Skip to main content
Disciplines
Automotive Business IT + Informatics Construction + Real Estate Electrical Engineering + Electronics Energy + Sustainability Insurance + Risk Finance + Banking Management + Leadership Marketing + Sales Mechanical Engineering + Materials
Events
DE
EN
Books
Journals
Topic Page
Marketing
Start single access now
Access for companies
EXTENDED SEARCH
Log in
Top
Published in:
Cover of the book

2018 | OriginalPaper | Chapter

Synthesis of N-Linked Glycopeptides Using Convergent Enzymatic Glycosylation Combined with SPPS

Authors : Renata Kowalczyk, Harveen Kaur, Antony J. Fairbanks, Margaret A. Brimble

Published in: Coupling and Decoupling of Diverse Molecular Units in Glycosciences

Publisher: Springer International Publishing

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

Glycosylation of peptides and proteins has emerged as a promising strategy to improve the pharmacokinetic profile of peptide- and protein-based therapeutics. The synthesis of pure homogeneous N-linked glycopeptides and glycoproteins is a challenging task, and efficient routes to access them are in high demand. Endo-β-N-acetylglucosaminidise catalysed glycosylation of N-acetylglucosamine-tagged peptides, using activated oligosaccharide oxazolines as donors, has recently attracted attention due to the relative simplicity by which the process convergently affords glycoconjugates with complete control of stereo- and regioselectivity. Herein, a brief review of some examples of recent enzyme-mediated N-glycosylation used to synthesise glycopeptides with therapetic potential is provided.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

inform now
next chapter Synthetic Antitumor Vaccines Through Coupling of Mucin Glycopeptide Antigens to Proteins
Literature
1.
Spiro RG (2002) Protein glycosylation: nature, distribution, enzymatic formation, and disease implications of glycopeptide bonds. Glycobiology 12:43R–56RCrossRef
2.
Meledeo MA, Yarema KJ, Begley TP (2007) Glycan biosynthesis in mammals, in wiley encyclopedia of chemical biology. Wiley, New Jersey
3.
Lafite P, Daniellou R (2012) Rare and unusual glycosylation of peptides and proteins. Nat Prod Rep 29:729–738CrossRef
4.
Haltiwanger RS, Lowe JB (2004) Role of Glycosylation in Development. Annu Rev Biochem 73:491–537CrossRef
5.
Dube DH, Bertozzi CR (2005) Glycans in cancer and inflammation-potential for therapeutics and diagnostics. Nat Rev Drug Discov 4:477–488CrossRef
6.
Dwek RA (1996) Glycobiology: toward understanding the function of sugars. Chem Rev 96:683–720CrossRef
7.
Imperiali B, O’Connor SE (1999) Effect of N-linked glycosylation on glycopeptide and glycoprotein structure. Curr Opin Chem Biol 3:643–649CrossRef
8.
Wyss DF, Choi JS (1995) Conformation and function of the N-linked glycan in the adhesion domain of human CD2. Science 269:1270CrossRef
9.
Opdenakker G, Rudd PM, Ponting CP, Dwek RA (1993) Concepts and principles of glycobiology. FASEB J 7:1330–1337
10.
Erbayraktar S, Grasso G, Sfacteria A, Xie Q-W, Coleman T, Kreilgaard M, Torup L, Sager T, Erbayraktar Z, Gokmen N, Yilmaz O, Ghezzi P, Villa P, Fratelli M, Casagrande S, Leist M, Helboe L, Gerwein J, Christensen S, Geist MA, Pedersen LØ, Cerami-Hand C, Wuerth J-P, Cerami A, Brines M (2003) Asialoerythropoietin is a nonerythropoietic cytokine with broad neuroprotective activity in vivo. Proc Nat Acad Sci USA 100:6741–6746CrossRef
11.
Schachter H, Freeze HH (2009) Glycosylation diseases: quo vadis? Biochim Biophys Acta Mol Basis Dis 1792:925–930
12.
Murakami Y, Kinoshita T (2015) Congenital Disorders of Glycosylation: Glycosylphosphatidylinositol (GPI)-Related. In: Taniguchi N, Endo T, Hart GW, Seeberger PH, Wong C-H (eds) Glycoscience: biology and medicine. Springer, Japan, pp 1229–1236
13.
Akimoto Y, Miura Y, Endo T, Kawakami H, Hart G (2015) Diabetes and O-GlcNAcylation. In: Taniguchi N, Endo T, Hart GW, Seeberger PH, Wong C-H (eds) Glycoscience: biology and medicine. Springer, Japan, pp 1207–1212
14.
Hart GW, Housley MP, Slawson C (2007) Cycling of O-linked β-N-acetylglucosamine on nucleocytoplasmic proteins. Nature 446:1017–1022CrossRef
15.
Zeidan Q, Hart GW (2010) The intersections between O-GlcNAcylation and phosphorylation: implications for multiple signaling pathways. J Cell Sci 123:13–22CrossRef
16.
Stowell SR, Ju T, Cummings RD (2015) Protein Glycosylation in Cancer. Annu Rev Pathol Mech Dis 10:473–510CrossRef
17.
Korekane H, Taniguchi N (2015) Glycosylation in cancer: enzymatic basis for alterations in N-glycan branching. In: Taniguchi N, Endo T, Hart GW, Seeberger PH, Wong C-H (eds) Glycoscience: biology and medicine. Springer, Japan, pp 1349–1356
18.
Schedin-Weiss S, Winblad B, Tjernberg LO (2014) The role of protein glycosylation in Alzheimer disease. FEBS J 281:46–62CrossRef
19.
Gao C, Taniguchi N (2015) Chronic Obstructive Pulmonary Disease (COPD). In: Taniguchi N, Endo T, Hart GW, Seeberger PH, Wong C-H (eds) Glycoscience: Biology and Medicine. Springer, Japan, pp 1267–1274
20.
Solá RJ, Griebenow K (2009) Effects of Glycosylation on the Stability of Protein Pharmaceuticals. J Pharm Sci 98:1223–1245CrossRef
21.
Solá RJ, Griebenow K (2010) Glycosylation of Therapeutic Proteins: an effective strategy to optimize efficacy. BioDrugs 24:9–21CrossRef
22.
Ueda T, Tomita K, Notsu Y, Ito T, Fumoto M, Takakura T, Nagatome H, Takimoto A, Mihara SI, Togame H, Kawamoto K, Iwasaki T, Asakura K, Oshima T, Hanasaki K, Nishimura SI, Kondo H (2009) Chemoenzymatic Synthesis of Glycosylated Glucagon-like Peptide 1: effect of glycosylation on proteolytic resistance and in vivo blood glucose-lowering activity. J Am Chem Soc 131:6237–6245CrossRef
23.
Sinclair AM, Elliott S (2005) Glycoengineering: the effect of glycosylation on the properties of therapeutic proteins. J Pharm Sci 94:1626–1635CrossRef
24.
Costa AR, Rodrigues ME, Henriques M, Oliveira R, Azeredo J (2014) Glycosylation: impact, control and improvement during therapeutic protein production. Crit Rev Biotechnol 34:281–299CrossRef
25.
Li HJ, d’Anjou M (2009) Pharmacological significance of glycosylation in therapeutic proteins. Curr Opin Biotechnol 20:678–684CrossRef
26.
Jefferis R (2009) Glycosylation as a strategy to improve antibody-based therapeutics. Nat Rev Drug Discov 8:226–234CrossRef
27.
Sato M, Furuike T, Sadamoto R, Fujitani N, Nakahara T, Niikura K, Monde K, Kondo H, Nishimura SI (2004) Glycoinsulins: Dendritic sialyloligosaccharide-displaying insulins showing a prolonged blood-sugar-lowering activity. J Am Chem Soc 126:14013–14022CrossRef
28.
Ueda T, Ito T, Tomita K, Togame H, Fumoto M, Asakura K, Oshima T, Nishimura SI, Hanasaki K (2010) Identification of glycosylated exendin-4 analogue with prolonged blood glucose-lowering activity through glycosylation scanning substitution. Bioorg Med Chem Lett 20:4631–4634CrossRef
29.
Runkel L, Meier W, Pepinsky RB, Karpusas M, Whitty A, Kimball K, Brickelmaier M, Muldowney C, Jones W, Goelz SE (1998) Structural and functional differences between glycosylated and non-glycosylated forms of human interferon-β (IFN-β). Pharm Res 15:641–649CrossRef
30.
Lappin TRJ, Maxwell AP (1989) Chemistry and assays of erythropoietin. In: Erythropoietin, W. Jelkmann and A. J. Gross, Editors. 1989, Springer Berlin Heidelberg: Berlin, Heidelberg. p. 7–18
31.
32.
Gamblin DP, Scanlan EM, Davis BG (2009) Glycoprotein synthesis: an update. Chem Rev 109:131–163CrossRef
33.
Wang L-X, Amin Mohammed N (2014) Chemical and chemoenzymatic synthesis of glycoproteins for deciphering functions. Chem Biol 21:51–66
34.
Wang L-X, Davis BG (2013) Realizing the promise of chemical glycobiology. Chem Sci 4:3381–3394CrossRef
35.
Unverzagt C, Kajihara Y (2013) Chemical assembly of N-glycoproteins: a refined toolbox to address a ubiquitous posttranslational modification. Chem Soc Rev 42:4408–4420CrossRef
36.
Izumi M, Okamoto R, Kajihara Y (2015) Chemical synthesis of homogeneous glycoproteins. In: Taniguchi N, Endo T, Hart GW, Seeberger PH, Wong C-H (eds) Glycoscience: biology and medicine. Springer, Japan, pp 313–321
37.
Westerlind U (2012) Synthetic glycopeptides and glycoproteins with applications in biological research. Beilstein J Org Chem 8:804–818CrossRef
38.
Fernández-Tejada A, Brailsford J, Zhang Q, Shieh J-H, Moore MAS, Danishefsky SJ (2015) Total synthesis of glycosylated proteins. In: Liu L (ed) Protein ligation and total synthesis I. Springer International Publishing, Cham, pp 1–26
39.
Kajihara Y, Yamamoto N, Okamoto R, Hirano K, Murase T (2010) Chemical synthesis of homogeneous glycopeptides and glycoproteins. Chem Rec 10:80–100CrossRef
40.
Payne RJ, Wong C-H (2010) Advances in chemical ligation strategies for the synthesis of glycopeptides and glycoproteins. Chem Commun 46:21–43CrossRef
41.
Rich JR, Withers SG (2009) Emerging methods for the production of homogeneous human glycoproteins. Nat Chem Biol 5:206–215CrossRef
42.
Xu C, Li X (2015) Glycopeptide/glycoprotein synthesis. In: Taniguchi N, Endo T, Hart GW, Seeberger PH, Wong C-H (eds) Glycoscience: biology and medicine. Springer, Japan, pp 323–330
43.
Fairbanks AJ (2013) Endohexosaminidase-catalyzed synthesis of glycopeptides and proteins. Pure Appl Chem 85:1847–1863CrossRef
44.
Ellgaard L, Helenius A (2003) Quality control in the endoplasmic reticulum. Nat Rev Mol Cell Biol 4:181CrossRef
45.
Stanley P, Schachter H, Taniguchi N (2009) N-glycans. In: Varki A, Cummings RD, Esko JD, Freeze HH, Stanley P, Bertozzi CR, Hart GW, Etzler ME (eds) Essentials of glycobiology. Cold Spring Harbor Laboratory Press, New York
46.
Herzner H, Reipen T, Schultz M, Kunz H (2000) Synthesis of glycopeptides containing carbohydrate and peptide recognition motifs. Chem Rev 100:4495–4538CrossRef
47.
Rudd PM, Dwek RA (1997) Glycosylation: heterogeneity and the 3D structure of proteins. Crit Rev Biochem Mol Biol 32:1–100CrossRef
48.
Brimble MA, Kowalczyk R, Harris PWR, Dunbar PR, Muir VJ (2008) Synthesis of fluorescein-labelled O-mannosylated peptides as components for synthetic vaccines: comparison of two synthetic strategies. Org Biomol Chem 6:112–121CrossRef
49.
Miller N, Williams GM, Brimble MA (2009) Synthesis of fish antifreeze neoglycopeptides using microwave-assisted “click chemistry”. Org Lett 11:2409–2412CrossRef
50.
Kowalczyk R, Harris PWR, Dunbar RP, Brimble MA (2009) Stability of 5(6)-carboxyfluorescein in microwave-assisted synthesis of fluorescein-labelled O-dimannosylated peptides. Synthesis 2009:2210–2222CrossRef
51.
Lee DJ, Mandal K, Harris PWR, Brimble MA, Kent SBH (2009) A one-pot approach to neoglycopeptides using orthogonal native chemical ligation and click chemistry. Org Lett 11:5270–5273CrossRef
52.
Lee DJ, Harris PWR, Kowalczyk R, Dunbar PR, Brimble MA (2010) Microwave-assisted synthesis of fluorescein-labelled GalNAcα1-O-Ser/Thr (Tn) glycopeptides as immunological probes. Synthesis 2010:763–769CrossRef
53.
Peltier R, Evans CW, DeVries AL, Brimble MA, Dingley AJ, Williams DE (2010) Growth habit modification of ice crystals using antifreeze glycoprotein (AFGP) analogues. Cryst Growth Des 10:5066–5077CrossRef
54.
Lee DJ, Harris PWR, Brimble MA (2011) Synthesis of MUC1 neoglycopeptides using efficient microwave-enhanced chaotrope-assisted click chemistry. Org Biomol Chem 9:1621–1626CrossRef
55.
Lee DJ, Yang S-H, Williams GM, Brimble MA (2012) Synthesis of multivalent neoglyconjugates of MUC1 by the conjugation of carbohydrate-centered, triazole-linked gllycoclusters to MUC1 peptides using click chemistry. J Org Chem 77:7564–7571CrossRef
56.
Brimble MA, Edwards PJ, Harris PWR, Norris GE, Patchett ML, Wright TH, Yang S-H, Carley SE (2015) Synthesis of the antimicrobial S-linked glycopeptide, glycocin F. Chem Eur J 21:3556–3561CrossRef
57.
McIntosh JD, Brimble MA, Brooks AES, Dunbar PR, Kowalczyk R, Tomabechi Y, Fairbanks AJ (2015) Convergent chemo-enzymatic synthesis of mannosylated glycopeptides; targeting of putative vaccine candidates to antigen presenting cells. Chem Sci 6:4636–4642CrossRef
58.
Kowalczyk R, Brimble MA, Tomabechi Y, Fairbanks AJ, Fletcher M, Hay DL (2014) Convergent chemoenzymatic synthesis of a library of glycosylated analogues of pramlintide: structure-activity relationships foramyl in receptor agonism. Org Biomol Chem 12:8142–8151CrossRef
59.
Reichert JM (2012) Marketed therapeutic antibodies compendium. mAbs 4:413–415
60.
61.
Bang LM, Keating GM (2004) Adalimumab a review of its use in rheumatoid arthritis. BioDrugs 18:121–139CrossRef
62.
Mazumdar S, Greenwald D (2009) Golimumab. mAbs 1:422–431
63.
Swiech K, de Freitas M, Covas D, Picanço-Castro V (2015) Recombinant glycoprotein production in human cell lines. In: García-Fruitós E (ed) Insoluble proteins. Springer, New York, pp 223–240
64.
Hamilton SR, Davidson RC, Sethuraman N, Nett JH, Jiang Y, Rios S, Bobrowicz P, Stadheim TA, Li H, Choi B-K, Hopkins D, Wischnewski H, Roser J, Mitchell T, Strawbridge RR, Hoopes J, Wildt S, Gerngross TU (2006) Humanization of yeast to produce complex terminally sialylated glycoproteins. Science 313:1441–1443CrossRef
65.
Hamilton SR, Bobrowicz P, Bobrowicz B, Davidson RC, Li H, Mitchell T, Nett JH, Rausch S, Stadheim TA, Wischnewski H, Wildt S, Gerngross TU (2003) Production of complex human glycoproteins in yeast. Science 301:1244–1246CrossRef
66.
Wang L-X, Lomino JV (2012) Emerging technologies for making glycan-defined glycoproteins. ACS Chem Biol 7:110–122CrossRef
67.
Fernandez-Tejada A, Danishefsky SJ (2014) Chapter 25 Development of cancer vaccines from fully synthetic mucin-based glycopeptide antigens. A vision on mucins from the bioorganic chemistry perspective. In: Carbohydrate Chemistry, vol 40. The Royal Society of Chemistry, pp 533–563
68.
Gaidzik N, Westerlind U, Kunz H (2013) The development of synthetic antitumour vaccines from mucin glycopeptide antigens. Chem Soc Rev 42:4421–4442CrossRef
69.
Payne RJ (2013) Total synthesis of erythropoietin through the development and exploitation of enabling synthetic technologies. Angew Chem Int Ed 52:505–507CrossRef
70.
Kajihara Y, Okamoto R, Yamamoto N, Izumi M (2010) Chapter twenty-four—synthesis of glycopeptides. In: Minoru F (ed) Methods in enzymology. Academic Press, pp 503–519
71.
Panda SS, Jones RA, Dennis Hall C, Katritzky AR (2015) Applications of chemical ligation in peptide synthesis via acyl transfer. In: Liu L (ed) Protein ligation and total synthesis I. Springer International Publishing, Cham, pp 229–265
72.
Behrendt R, White P, Offer J (2016) Advances in Fmoc solid-phase peptide synthesis. J Pept Sci 22:4–27CrossRef
73.
Merrifield RB (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J Am Chem Soc 85:2149–2154CrossRef
74.
Dawson P, Muir T, Clark-Lewis I, Kent S (1994) Synthesis of proteins by native chemical ligation. Science 266:776–779CrossRef
75.
Muir TW (2003) Semisynthesis of proteins by expressed protein ligation. Annu Rev Biochem 72:249–289CrossRef
76.
Xu C, Lam HY, Zhang Y, Li X (2013) Convergent synthesis of MUC1 glycopeptides via serine ligation. Chem Commun 49:6200–6202CrossRef
77.
Zhang Y, Xu C, Lam HY, Lee CL, Li X (2013) Protein chemical synthesis by serine and threonine ligation. Proc Nat Acad Sci USA 110:6657–6662CrossRef
78.
Li X, Lam HY, Zhang Y, Chan CK (2010) Salicylaldehyde ester-induced chemoselective peptide ligations: enabling generation of natural peptidic linkages at the serine/threonine sites. Org Lett 12:1724–1727CrossRef
79.
Sakamoto I, Tezuka K, Fukae K, Ishii K, Taduru K, Maeda M, Ouchi M, Yoshida K, Nambu Y, Igarashi J, Hayashi N, Tsuji T, Kajihara Y (2012) Chemical synthesis of homogeneous human glycosyl-interferon-β that exhibits potent antitumor activity in vivo. J Am Chem Soc 134:5428–5431CrossRef
80.
Izumi M, Makimura Y, Dedola S, Seko A, Kanamori A, Sakono M, Ito Y, Kajihara Y (2012) Chemical synthesis of intentionally misfolded homogeneous glycoprotein: a unique approach for the study of glycoprotein quality Control. J Am Chem Soc 134:7238–7241CrossRef
81.
Hojo H, Tanaka H, Hagiwara M, Asahina Y, Ueki A, Katayama H, Nakahara Y, Yoneshige A, Matsuda J, Ito Y, Nakahara Y (2012) Chemoenzymatic Synthesis of hydrophobic glycoprotein: synthesis of saposin c carrying complex-type Carbohydrate. J Org Chem 77:9437–9446CrossRef
82.
Piontek C, Ring P, Harjes O, Heinlein C, Mezzato S, Lombana N, Pöhner C, Püttner M, Varón Silva D, Martin A, Schmid FX, Unverzagt C (2009) Semisynthesis of a homogeneous glycoprotein enzyme: Ribonuclease C: part 1. Angew Chem Int Ed 48:1936–1940CrossRef
83.
Piontek C, Varón Silva D, Heinlein C, Pöhner C, Mezzato S, Ring P, Martin A, Schmid FX, Unverzagt C (2009) Semisynthesis of a homogeneous glycoprotein enzyme: Ribonuclease C: part 2. Angew Chem Int Ed 48:1941–1945CrossRef
84.
Haase C, Seitz O (2007) Chemical synthesis of glycopepticles. In: Wittmann V (ed) Glycopeptides and glycoproteins: synthesis, structure, and application. Springer, Berlin, pp 1–36
85.
Palitzsch B, Gaidzik N, Stergiou N, Stahn S, Hartmann S, Gerlitzki B, Teusch N, Flemming P, Schmitt E, Kunz H (2016) A synthetic glycopeptide vaccine for the induction of a monoclonal antibody that differentiates between normal and tumor mammary cells and enables the diagnosis of human pancreatic cancer. Angew Chem Int Ed 55:2894–2898CrossRef
86.
Hartmann S, Palitzsch B, Glaffig M, Kunz H (2014) Chapter 24 tumour-associated glycopeptide antigens and their modification in anticancer vaccines. In: Carbohydrate chemistry: volume 40. The Royal Society of Chemistry, pp 506–532
87.
Kowalczyk R, Harris PWR, Dunbar RP, Brimble MA (2009) Stability of 5(6)-carboxyfluorescein in microwave-assisted synthesis of fluorescein-labelled o-dimannosylated peptides. Synthesis, 2210–2222
88.
Lee DJ, Harris PWR, Kowalczyk R, Dunbar PR, Brimble MA (2010) Microwave-assisted synthesis of fluorescein-labelled GalNAc α 1-O-Ser/Thr (Tn) glycopeptides as immunological probes. Synthesis-Stuttgart, 763–769
89.
Yamamoto N, Ohmori Y, Sakakibara T, Sasaki K, Juneja LR, Kajihara Y (2003) Solid-phase synthesis of sialylglycopeptides through selective Esterification of the sialic acid residues of an asn-linked complex-type sialyloligosaccharide. Angew Chem Int Ed 42:2537–2540CrossRef
90.
Kajihara Y, Suzuki Y, Yamamoto N, Sasaki K, Sakakibara T, Juneja LR (2004) Prompt chemoenzymatic synthesis of diversecomplex-type oligosaccharides and Its application to the solid-phase synthesisof a glycopeptide with asn-linked sialyl-undeca- and asialo-nonasaccharides. Chem Eur J 10:971–985CrossRef
91.
Murakami M, Kiuchi T, Nishihara M, Tezuka K, Okamoto R, Izumi M, Kajihara Y (2016) Chemical synthesis of erythropoietin glycoforms for insights into the relationship between glycosylation pattern and bioactivity. Sci Adv 2:1–12CrossRef
92.
Murakami M, Okamoto R, Izumi M, Kajihara Y (2012) Chemical synthesis of an erythropoietin glycoform containing a complex-type Disialyloligosaccharide. Angew Chem Int Ed 51:3567–3572CrossRef
93.
Yamamoto N, Takayanagi A, Yoshino A, Sakakibara T, Kajihara Y (2007) An approach for a synthesis of asparagine-linked sialylglycopeptides having intact and homogeneous complex-type undecadisialyloligosaccharides. Chem Eur J 13:613–625CrossRef
94.
Cohen-Anisfeld ST, Lansbury PT (1993) A practical, convergent method for glycopeptide synthesis. J Am Chem Soc 115:10531–10537CrossRef
95.
Anisfeld ST, Lansbury PT (1990) A convergent approach to the chemical synthesis of asparagine-linked glycopeptides. J Org Chem 55:5560–5562CrossRef
96.
Wang P, Dong S, Brailsford JA, Iyer K, Townsend SD, Zhang Q, Hendrickson RC, Shieh J, Moore MAS, Danishefsky SJ (2012) At Last: erythropoietin as a single Glycoform. Angew Chem Int Ed 51:11576–11584CrossRef
97.
Wang P, Dong S, Shieh J-H, Peguero E, Hendrickson R, Moore MAS, Danishefsky SJ (2013) Erythropoietin derived by chemical synthesis. Science 342:1357–1360CrossRef
98.
Yan LZ, Dawson PE (2001) Synthesis of peptides and proteins without cysteine Residues by native chemical ligation combined with desulfurization. J Am Chem Soc 123:526–533CrossRef
99.
Wang P, Aussedat B, Vohra Y, Danishefsky SJ (2012) An advance in the chemical synthesis of homogeneous N-linked glycopolypeptides by convergent aspartylation. Angew Chem Int Ed 51:11571–11575CrossRef
100.
Ullmann V, Rädisch M, Boos I, Freund J, Pöhner C, Schwarzinger S, Unverzagt C (2012) Convergent solid-phase synthesis of NGlycopeptides facilitated by pseudoprolines at consensus-sequence Ser/Thr residues. Angew Chem Int Ed 51:11566–11570CrossRef
101.
Katoh T, Yamamoto K (2015) Glycoenzymes in glycan analysis and synthesis. In: Taniguchi N, Endo T, Hart GW, Seeberger PH, Wong C-H (eds) Glycoscience: biology and medicine. Springer, Japan, pp 379–389
102.
Malet C, Planas A (1998) From β-glucanase to β-glucansynthase: glycosyl transfer to α-glycosyl fluorides catalyzed by a mutant endoglucanase lacking its catalytic nucleophile. FEBS Lett 440:208–212CrossRef
103.
Mackenzie LF, Wang Q, Warren RAJ, Withers SG (1998) Glycosynthases: mutant glycosidases for oligosaccharide synthesis. J Am Chem Soc 120:5583–5584CrossRef
104.
Hancock SM, Vaughan MD, Withers SG (2006) Engineering of glycosidases and glycosyltransferases. Curr Opin Chem Biol 10:509–519CrossRef
105.
Yamamoto K (2015) Endo-enzymes. In: Taniguchi N, Endo T, Hart GW, Seeberger PH, Wong C-H (eds) Glycoscience: biology and medicine. Springer, Japan, pp 391–399
106.
107.
Murakami S, Takaoka Y, Ashida H, Yamamoto K, Narimatsu H, Chiba Y (2013) Identification and characterization of endo-β-nacetylglucosaminidas from methylotrophic yeast Ogataea minuta. Glycobiology 23:736–744CrossRef
108.
Yamamoto K (2001) Chemo-Enzymatic synthesis of bioactive glycopeptide using microbial endoglycosidase. J Biosci Bioeng 92:493–501CrossRef
109.
Kadowaki S, Yamamoto K, Fujisaki M, Kumagai H, Tochikura T (1988) A novel endo-β-N-acetylglucosaminidase acting on complex oligosaccharides of glycoproteins in a fungus. Agric Biol Chem 52:2387–2389
110.
Yamamoto KJ, Kadowaki S, Watanabe J, Kumagai H (1994) Transglycosylation activity of mucor hiemalis endo-β-N-acetylglucosaminidase which transfers complex oligosaccharides to the N-Acetylglucosamine moieties of peptides. Biochem Biophys Res Commun 203:244–252CrossRef
111.
Haneda K, Inazu T, Yamamoto K, Kumagai H, Nakahara Y, Kobata A (1996) Transglycosylation of intact sialo complex-type oligosaccharides to the N-acetylglucosamine moieties of glycopeptides by Mucor hiemalis endo-β-N-acetylglucosaminidase. Carbohydr Res 292:61–70CrossRef
112.
Yamamoto K, Fujimori K, Haneda K, Mizuno M, Inazu T, Kumagai H (1997) Chemoenzymatic synthesis of a novel glycopeptide using a microbial endoglycosidase. Carbohydr Res 305:415–422CrossRef
113.
Mizuno M, Haneda K, Iguchi R, Muramoto I, Kawakami T, Aimoto S, Yamamoto K, Inazu T (1999) Synthesis of a glycopeptide containing oligosaccharides: chemoenzymatic synthesis of eel calcitonin analogues having natural N-linked oligosaccharides. J Am Chem Soc 121:284–290CrossRef
114.
Haneda K, Inazu T, Mizuno M, Iguchi R, Yamamoto K, Kumagai H, Aimoto S, Suzuki H, Noda T (1998) Chemo-enzymatic synthesis of calcitonin derivatives containing N-linked oligosaccharides. Bioorg Med Chem Lett 8:1303–1306CrossRef
115.
Yamanoi T, Tsutsumida M, Oda Y, Akaike E, Osumi K, Yamamoto K, Fujita K (2004) Transglycosylation reaction of mucor hiemalis endo-β-N-acetylglucosaminidase using sugar derivatives modified at C-1 or C-2 as oligosaccharide acceptors. Carbohydr Res 339:1403–1406CrossRef
116.
Osumi K, Makino Y, Akaike E, Yamanoi T, Mizuno M, Noguchi M, Inazu T, Yamamoto K, Fujita K (2004) Mucor hiemalis endo-β-N-acetylglucosaminidase can transglycosylate a bisecting hybrid-type oligosaccharide from an ovalbumin glycopeptide. Carbohydr Res 339:2633–2635CrossRef
117.
Haneda K, Takeuchi M, Tagashira M, Inazu T, Toma K, Isogai Y, Hori M, Kobayashi K, Takeuchi M, Takegawa K, Yamamoto K (2006) Chemo-enzymatic synthesis of eel calcitonin glycosylated at two sites with the same and different carbohydrate structures. Carbohydr Res 341:181–190CrossRef
118.
Makimura Y, Watanabe S, Suzuki T, Suzuki Y, Ishida H, Kiso M, Katayama T, Kumagai H, Yamamoto K (2006) Chemoenzymatic synthesis and application of a sialoglycopolymer with a chitosan backbone as a potent inhibitor of human influenza virus hemagglutination. Carbohydr Res 341:1803–1808CrossRef
119.
Yamanoi T, Yoshida N, Oda Y, Akaike E, Tsutsumida M, Kobayashi N, Osumi K, Yamamoto K, Fujita K, Takahashi K, Hattori K (2005) Synthesis of mono-glucose-branched cyclodextrins with a high inclusion ability for doxorubicin and their efficient glycosylation using Mucor hiemalis endo-β-N-acetylglucosaminidase. Bioorg Med Chem Lett 15:1009–1013CrossRef
120.
Tomabechi Y, Inazu T (2011) Preparation of pseudo glycoamino acid and its application to glycopeptide synthesis. Tetrahedron Lett 52:6504–6507CrossRef
121.
Takegawa K, Nakoshi M, Iwahara S, Yamamoto K, Tochikura T (1989) Induction and purification of endo-β-N-acetylglucosaminidase from arthrobacter protophormiae grown in ovalbumin. Appl Environ Microbiol 55:3107–3112
122.
Fan J-Q, Huynh LH, Reinhold BB, Reinhold VN, Takegawa K, Iwahara S, Kondo A, Kato I, Lee YC (1996) Transfer of Man9GlcNAc tol-fucose by endo-β-N-acetylglucosaminidase from arthrobacter protophormiae. Glycoconjugate J 13:643–652CrossRef
123.
Takegawa K, Tabuchi M, Yamaguchi S, Kondo A, Kato I, Iwahara S (1995) Synthesis of neoglycoproteins using oligosaccharide-transfer activity with endo-β-N-acetylglucosaminidase. J Biol Chem 270:3094–3099CrossRef
124.
Fan J-Q, Quesenberry MS, Takegawa K, Iwahara S, Kondo A, Kato I, Lee YC (1995) Synthesis of Neoglycoconjugates by Transglycosylation with Arthrobacter protophormiae endo-β-N-acetylglucosaminidase: demonstration of a macro-cluster effect for mannose-binding proteins. J Biol Chem 270:17730–17735CrossRef
125.
Fan J-Q, Takegawa K, Iwahara S, Kondo A, Kato I, Abeygunawardana C, Lee YC (1995) Enhanced transglycosylation activity of arthrobacter protophormiae endo-β-N-acetylglucosaminidase in media containing organic solvents. J Biol Chem 270:17723–17729CrossRef
126.
Takegawa K, Fujita K, Fan J-Q, Tabuchi M, Tanaka N, Kondo A, Iwamoto H, Kato I, Lee YC, Iwahara S (1998) Enzymatic synthesis of a neoglycoconjugate by transglycosylation with arthrobacter endo-β-N-acetylglucosaminidase: a substrate for colorimetric detection of endo-β-N-acetylglucosaminidase activity. Anal Biochem 257:218–223CrossRef
127.
Fujita K, Tanaka N, Sano M, Kato I, Asada Y, Takegawa K (2000) Synthesis of neoglycoenzymes with homogeneous Nlinked oligosaccharides using Immobilized endo-β-N-acetylglucosaminidase A. Biochem Biophys Res Commun 267:134–138CrossRef
128.
Takegawa K, Yamabe K, Fujita K, Tabuchi M, Mita M, Izu H, Watanabe A, Asada Y, Sano M, Kondo A, Kato I, Iwahara S (1997) Cloning, sequencing, and expression of arthrobacter protophormiae endo-β-N-acetylglucosaminidase in escherichia coli. Arch Biochem Biophys 338:22–28CrossRef
129.
Muramatsu H, Tachikui H, Ushida H, Song X-J, Qiu Y, Yamamoto S, Muramatsu T (2001) Molecular cloning and expression of endo-β-N-acetylglucosaminidase D, which acts on the core structure of complex type asparagine-linked oligosaccharides. J Biochem 129:923–928CrossRef
130.
Parsons TB, Patel MK, Boraston AB, Vocadlo DJ, Fairbanks AJ (2010) Streptococcus pneumoniae endohexosaminidase D; feasibility of using N-glycan oxazoline donors for synthetic glycosylation of a GlcNAc-asparagine acceptor. Org Biomol Chem 8:1861–1869CrossRef
131.
Fujita K, Takami H, Yamamoto K, Takegawa K (2004) Characterization of endo-β-N-acetylglucosaminidase from alkaliphilic bacillus halodurans C-125. Biosci Biotechnol Biochem 68:1059–1066CrossRef
132.
Tarentino AL, Maley F (1974) Purification and properties of an endo-β-N-acetylglucosaminidase from streptomyces griseus. J Biol Chem 249:811–817
133.
Goodfellow JJ, Baruah K, Yamamoto K, Bonomelli C, Krishna B, Harvey DJ, Crispin M, Scanlan CN, Davis BG (2012) An endoglycosidase with alternative glycan specificity allows broadened glycoprotein remodelling. J Am Chem Soc 134:8030–8033CrossRef
134.
Collin M, Olsén A (2001) EndoS, a novel secreted protein from streptococcus pyogenes with endoglycosidase activity on human IgG. EMBO J 20:3046–3055CrossRef
135.
Huang W, Li J, Wang L-X (2011) Unusual transglycosylation activity of flavobacterium meningosepticum endoglycosidases enables convergent chemoenzymatic synthesis of core fucosylated complex N-glycopeptides. ChemBioChem 12:932–941CrossRef
136.
Trimble RB, Tarentino AL (1991) Identification of distinct endoglycosidase (endo) activities in flavobacterium meningosepticum: endo F1, endo F2, and endo F3. Endo F1 and endo H hydrolyze only high mannose and hybrid glycans. J Biol Chem 266:1646–1651
137.
Tarentino AL, Plummer TH Jr (1994) [4] Enzymatic deglycosylation of asparagine-linked glycans: purification, properties, and specificity of oligosaccharide-cleaving enzymes from flavobacterium meningosepticum. In: Methods in enzymology, vol 230. Academic Press, Cambridge, pp 44–57
138.
Zhao G, Liu Y, Wu Z, Zhu H, Yu Z, Fang J, Wang P (2015) Chemoenzymatic synthesis of glycoproteins. In: Taniguchi N, Endo T, Hart GW, Seeberger PH, Wong C-H (eds) Glycoscience: biology and medicine. Springer, Japan, pp 427–435
139.
Wang L-X (2008) Chemoenzymatic synthesis of glycopeptides and glycoproteins through endoglycosidase-catalyzed transglycosylation. Carbohydr Res 343:1509–1522CrossRef
140.
Rising TWDE, Heidecke CD, Moir JWB, Ling ZL, Fairbanks AJ (2008) Endohexosaminidase-catalysed glycosylation with oxazoline donors: fine tuning of catalytic efficiency and reversibility. Chem Eur J 14:6444–6464CrossRef
141.
Rising TWDF, Claridge TDW, Davies N, Gamblin DP, Moir JWB, Fairbanks AJ (2006) Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation. Carbohydr Res 341:1574–1596CrossRef
142.
Rising TWDF, Claridge TDW, Moir JWB, Fairbanks AJ (2006) Endohexosaminidase M: exploring and exploiting enzyme substrate specificity. ChemBioChem 7:1177–1180CrossRef
143.
Parsons TB, Moir JWB, Fairbanks AJ (2009) Synthesis of a truncated bi-antennary complextype N-glycan oxazoline; glycosylation catalysed by the endohexosaminidases endo A and endo M. Org Biomol Chem 7:3128–3140CrossRef
144.
Huang W, Ochiai H, Zhang XY, Wang LX (2008) Introducing N-glycans into natural products through a chemoenzymatic approach. Carbohydr Res 343:2903–2913CrossRef
145.
Li B, Song HJ, Hauser S, Wang LX (2006) A highly efficient chemoenzymatic approach toward glycoprotein synthesis. Org Lett 8:3081–3084CrossRef
146.
Li B, Zeng Y, Hauser S, Song HJ, Wang LX (2005) Highly efficient endoglycosidase-catalyzed synthesis of glycopeptides using oligosaccharide oxazolines as donor substrates. J Am Chem Soc 127:9692–9693CrossRef
147.
Ochiai H, Huang W, Wang LX (2009) Endo-β-N-acetylglucosaminidase-catalyzed polymerization of β-Glcp-(1->4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation. Carbohydr Res 344:592–598CrossRef
148.
Wang LX, Song HJ, Liu SW, Lu H, Jiang SB, Ni JH, Li HG (2005) Chemoenzymatic synthesis of HIV-1 gp41 glycopeptides: effects of glycosylation on the anti-HIV activity and alpha-helix bundle-forming ability of peptide C34. ChemBioChem 6:1068–1074CrossRef
149.
Wei YD, Li CS, Huang W, Li B, Strome S, Wang LX (2008) Glycoengineering of human IgG1-Fc through combined yeast expression and in vitro chemoenzymatic glycosylation. Biochemistry 47:10294–10304CrossRef
150.
Zeng Y, Wang JS, Li B, Hauser S, Li HG, Wang LX (2006) Glycopeptide synthesis through endo-glycosidasecatalyzed oligosaccharide transfer of sugar oxazolines: probing substrate structural requirement. Chem Eur J 12:3355–3364CrossRef
151.
Fujita M, Shoda S-i, Haneda K, Inazu T, Takegawa K, Yamamoto K (2001) A novel disaccharide substrate having 1,2-oxazoline moiety for detection of transglycosylating activity of endoglycosidases. Biochim Biophys Acta Gen Subj 1528:9–14
152.
Fairbanks AJ (2011) Endohexosaminidase catalysed glycosylation with oxazoline donors: the development of robust biocatalytic methods for synthesis of defined homogeneous glycoconjugates. C R Chim 14:44–58CrossRef
153.
Heidecke CD, Ling Z, Bruce NC, Moir JWB, Parsons TB, Fairbanks AJ (2008) Enhanced glycosylation with mutants of endohexosaminidase A (endo A). ChemBioChem 9:2045–2051CrossRef
154.
Heidecke CD, Parsons TB, Fairbanks AJ (2009) Endohexosaminidase-catalysed glycosylation with oxazoline donors: effects of organic co-solvent and pH on reactions catalysed by endo A and endo M. Carbohydr Res 344:2433–2438CrossRef
155.
Li B, Zeng Y, Hauser S, Song H, Wang L-X (2005) Highly efficient endoglycosidase-catalyzed synthesis of glycopeptides using oligosaccharide oxazolines as donor substrates. J Am Chem Soc 127:9692–9693CrossRef
156.
Li H, Li B, Song H, Breydo L, Baskakov IV, Wang L-X (2005) Chemoenzymatic synthesis of HIV-1 V3 glycopeptides carrying two N-glycans and effects of glycosylation on the peptide domain. J Org Chem 70:9990–9996CrossRef
157.
Wang L-X, Song H, Liu S, Lu H, Jiang S, Ni J, Li H (2005) Chemoenzymatic synthesis of HIV-1 gp41 glycopeptides: effects of glycosylation on the anti-HIV activity and α-helix bundle-forming ability of peptide C34. ChemBioChem 6:1068–1074CrossRef
158.
Li B, Song H, Hauser S, Wang L-X (2006) A highly efficient chemoenzymatic approach toward glycoprotein synthesis. Org Lett 8:3081–3084CrossRef
159.
Zeng Y, Wang J, Li B, Hauser S, Li H, Wang L-X (2006) Glycopeptide synthesis through endo-glycosidase-catalyzed oligosaccharide yransfer of sugar pxazolines: probing substrate structural requirement. Chem Eur J 12:3355–3364CrossRef
160.
Ochiai H, Huang W, Wang L-X (2008) Expeditious chemoenzymatic synthesis of homogeneous N-glycoproteins carrying defined oligosaccharide ligands. J Am Chem Soc 130:13790–13803CrossRef
161.
Umekawa M, Huang W, Li B, Fujita K, Ashida H, Wang L-X, Yamamoto K (2008) Mutants of mucor hiemalis endo-β-N-acetylglucosaminidase show enhanced transglycosylation and glycosynthaselike activities. J Biol Chem 283:4469–4479CrossRef
162.
Li H, Singh S, Zeng Y, Song H, Wang L-X (2005) Chemoenzymatic synthesis of CD52 glycoproteins carrying native N-glycans. Bioorg Med Chem Lett 15:895–898CrossRef
163.
Wei Y, Li C, Huang W, Li B, Strome S, Wang L-X (2008) Glycoengineering of human IgG1-Fc through combined yeast expression and in vitro chemoenzymatic glycosylation. Biochemistry 47:10294–10304CrossRef
164.
Huang W, Li C, Li B, Umekawa M, Yamamoto K, Zhang X, Wang L-X (2009) Glycosynthases enable a highly efficient chemoenzymatic eynthesis of N-glycoproteins carrying intact natural N-glycans. J Am Chem Soc 131:2214–2223CrossRef
165.
Tomabechi Y, Krippner G, Rendle PM, Squire MA, Fairbanks AJ (2013) Glycosylation of pramlintide: synthetic glycopeptides that display in vitro and in vivo activities as amylin receptor agonists. Chem Eur J 19:15084–15088CrossRef
166.
167.
Fujita K, Takegawa K (2001) Tryptophan-216 is essential for the transglycosylation activity of endo-β-N-acetylglucosaminidase A. Biochem Biophys Res Commun 283:680–686CrossRef
168.
Umekawa M, Li CS, Higashiyama T, Huang W, Ashida H, Yamamoto K, Wang LX (2010) Efficient glycosynthase mutant derived from mucor hiemalis endo-b-N-acetylglucosaminidase capable of transferring oligosaccharide from both sugar oxazoline and natural N-glycan. J Biol Chem 285:511–521CrossRef
169.
Fan S-Q, Huang W, Wang L-X (2012) Remarkable transglycosylation activity of glycosynthase mutants of endo-D, an endo-β-N-acetylglucosaminidase from streptococcus pneumoniae. J Biol Chem 287:11272–11281CrossRef
170.
Huang W, Giddens J, Fan S-Q, Toonstra C, Wang L-X (2012) Chemoenzymatic glycoengineering of intact IgG antibodies for gain of functions. J Am Chem Soc 134:12308–12318CrossRef
171.
Parsons TB, Struwe WB, Gault J, Yamamoto K, Taylor TA, Raj R, Wals K, Mohammed S, Robinson CV, Benesch JLP, Davis BG (2016) Optimal synthetic glycosylation of a therapeutic antibody. Angew Chem Int Ed 55:2361–2367CrossRef
172.
Rosati S, van den Bremer ETJ, Schuurman J, Parren PWHI, Kamerling JP, Heck AJR (2013) In-depth qualitative and quantitative analysis of composite glycosylation profiles and other micro-heterogeneity on intactmonoclonal antibodies by high-resolution native mass spectrometry using a modified orbitrap. mAbs 5:917–924
173.
Lin C-W, Tsai M-H, Li S-T, Tsai T-I, Chu K-C, Liu Y-C, Lai M-Y, Wu C-Y, Tseng Y-C, Shivatare SS, Wang C-H, Chao P, Wang S-Y, Shih H-W, Zeng Y-F, You T-H, Liao J-Y, Tu Y-C, Lin Y-S, Chuang H-Y, Chen C-L, Tsai C-S, Huang C-C, Lin N-H, Ma C, Wu C-Y, Wong C-H (2015) A common glycan structure on immunoglobulin G for enhancement of effector functions. Proc Nat Acad Sci USA 112:10611–10616CrossRef
174.
Saini KS, Azim HA Jr, Cocorocchio E, Vanazzi A, Saini ML, Raviele PR, Pruneri G, Peccatori FA (2011) Rituximab in Hodgkin lymphoma: is the target always a hit? Cancer Treat Rev 37:385–390
175.
Ellis P (2008) Trastuzumab (Herceptin) a treatment for HER2-positive breast cancer. In: Handbook of therapeutic antibodies. Wiley-VCH Verlag GmbH, pp 1109–1130
176.
Tomabechi Y, Odate Y, Izumi R, Haneda K, Inazu T (2010) Acceptor specificity in the transglycosylation reaction using endo-M. Carbohydr Res 345:2458–2463CrossRef
177.
Tomabechi Y, Squire MA, Fairbanks AJ (2014) Endo-b-N-acetylglucosaminidase catalysed glycosylation: tolerance of enzymes to structural variation of the glycosyl amino acid acceptor. Org Biomol Chem 12:942–955CrossRef
178.
Boltje TJ, Buskas T, Boons G-J (2009) Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research. Nat Chem 1:611–622CrossRef
179.
Noguchi M, Tanaka T, Gyakushi H, Kobayashi A, Shoda S-I (2009) Efficient synthesis of sugar oxazolines from unprotected N-acetyl-2-amino sugars by using chloroformamidinium reagent in water. J Org Chem 74:2210–2212CrossRef
180.
Watt GM, Boons G-J (2004) A convergent strategy for the preparation of N-glycan core di-, tri-, and pentasaccharide thioaldoses for the site-specific glycosylation of peptides and proteins bearing free cysteines. Carbohydr Res 339:181–193CrossRef
181.
Seko A, Koketsu M, Nishizono M, Enoki Y, Ibrahim HR, Juneja LR, Kim M, Yamamoto T (1997) Occurrence of a sialylglycopeptide and free sialylglycans in hen's egg yolk. Biochim Biophys Acta Gen Subj 1335:23–32
182.
Evers DL, Hung RL, Thomas VH, Rice KG (1998) Preparative purification of a High-mannose typeN-glycan from soy bean agglutinin by hydrazinolysis and tyrosinamide derivatization. Anal Biochem 265:313–316CrossRef
183.
Liener IE (1955) The photometric determination of the hemagglutinating activity of soyin and crude soybean extracts. Arch Biochem Biophys 54:223–231CrossRef
184.
Wang L-X, Ni J, Singh S, Li H (2004) Binding of high-mannose-type oligosaccharides and synthetic oligomannose clusters to human antibody 2G12. Cell Chem Biol 11:127–134
185.
Specker D, Wittmann V (2007) Synthesis and application of glycopeptide and glycoprotein mimetics. In: Wittmann V (ed) Glycopeptides and glycoproteins: synthesis, structure, and application. Springer Berlin Heidelberg, Berlin, Heidelberg, pp 65–107
186.
Tornoe CW, Christensen C, Meldal M (2002)Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem 67:3057–3064CrossRef
187.
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew Chem Int Ed 41:2596–2599CrossRef
188.
Trabocchi A, Guarna A (2014) Click chemistry: the triazole ring as a privileged peptidomimetic scaffold. In: Peptidomimetics in organic and medicinal chemistry. Wiley, New Jersey, pp 99–121
189.
Miller N, Williams GM, Brimble MA (2010) Synthesis of fish antifreeze neoglycopeptides using microwave-assisted “Click Chemistry”. Org Lett 12:1375–1376CrossRef
190.
Wojnar JM, Lee DJ, Evans CW, Mandal K, Kent SBH, Brimble MA (2013) Neoglycoprotein synthesis using the copper-catalyzed azide–alkyne click reaction and native chemical ligation. In: Click chemistry in glycoscience. Wiley, New Jersey, pp 251–270
191.
Lim D, Brimble MA, Kowalczyk R, Watson AJA, Fairbanks AJ (2014) Protecting-group-free one-pot synthesis of glycoconjugates directly from reducing sugars. Angew Chem Int Ed 53:11907–11911CrossRef
192.
Grunberger GJ (2013) Novel therapies for the management of type 2 diabetes mellitus: part 1. Pramlintide and bromocriptine-QR. J Diabetes 5:110–117CrossRef
193.
Younk LM, Mikeladze M, Davis SN (2011) Pramlintide and the treatment of diabetes: a review of the data since its introduction. Expert Opin Pharmacother 12:1439–1451CrossRef
194.
Young AA, Vine W, Gedulin BR, Pittner R, Janes S, Gaeta LSL, Percy A, Moore CX, Koda JE, Rink TJ, Beaumont K (1996) Preclinical pharmacology of pramlintide in the rat: Comparisons with human and rat amylin. Drug Dev Res 37:231–248CrossRef
195.
Roberts AN, Leighton B, Todd JA, Cockburn D, Schofield PN, Sutton R, Holt S, Boyd Y, Day AJ, Foot EA, Willis AC, Reid KBM, Cooper GJS (1989) Molecular and functional-characterization of amylin, a peptide associated with type-2 diabetes-mellitus. Proc Nat Acad Sci USA 86:9662–9666CrossRef
196.
Maruyama K, Nagasawa H, Suzuki A (1999) 2,2'-bispyridyl disulfide rapidly induces intramolecular disulfide bonds in peptides. Peptides 20:881–884CrossRef
197.
Inazu T, Kobayashi K (1993) A new simple method for the synthesis of N(α)-Fmoc-N(b)-glycosylated-l-asparagine derivatives. Synlett, 869–870
198.
Katayama H, Asahina Y, Hojo H (2011) Chemical synthesis of the S-linked glycopeptide, sublancin. J Pept Sci 17:818–821CrossRef
199.
Umekawa M, Higashiyama T, Koga Y, Tanaka T, Noguchi M, Kobayashi A, Shoda S, Huang W, Wang LX, Ashida H, Yamamoto K (2010) Efficient transfer of sialo-oligosaccharide onto proteins by combined use of a glycosynthase-like mutant of mucor hiemalis endoglycosidase and synthetic sialo-complex-type sugar oxazoline. Biophys Acta Gen Subj 1800:1203–1209
200.
Hay DL, Christopoulos G, Christopoulos A, Poyner DR, Sexton PM (2005) Pharmacological discrimination of calcitonin receptor: receptor activity-modifying protein complexes. Mol Pharmacol 67:1655–1665CrossRef
201.
Tilakaratne N, Christopoulos G, Zumpe ET, Foord SM, Sexton PM (2000) Amylin receptor phenotypes derived from human calcitonin receptor/RAMP coexpression exhibit pharmacological differences dependent on receptor isoform and host cell environment. J Pharmacol Exp Ther 294:61–72
202.
Gingell JJ, Burns ER, Hay DL (2014) Activity of pramlintide, rat and human amylin but not Ab1-42 at human amylin receptors. Endocrinology 155:21–26CrossRef
203.
Vilaseca M, Nicolas E, Capdevila F, Giralt E (1998) Reduction of methionine sulfoxide with NH4I/TFA: compatibility with peptides containing cysteine and aromatic amino acids. Tetrahedron 54:15273–15286CrossRef
204.
Wang Z, Chinoy ZS, Ambre SG, Peng W, McBride R, de Vries RP, Glushka J, Paulson JC, Boons G-J (2013) A general strategy for the chemoenzymatic synthesis of asymmetrically branched N-glycans. Science 341:379–383CrossRef
Metadata
Title
Synthesis of N-Linked Glycopeptides Using Convergent Enzymatic Glycosylation Combined with SPPS
Authors
Renata Kowalczyk
Harveen Kaur
Antony J. Fairbanks
Margaret A. Brimble
Copyright Year
2018
Book
Coupling and Decoupling of Diverse Molecular Units in Glycosciences

Print ISBN: 978-3-319-65586-4

Electronic ISBN: 978-3-319-65587-1

Copyright Year: 2018

DOI
https://doi.org/10.1007/978-3-319-65587-1_1