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2015 | OriginalPaper | Chapter

SIGLEC-4 (MAG) Antagonists: From the Natural Carbohydrate Epitope to Glycomimetics

Authors : Oliver Schwardt, Soerge Kelm, Beat Ernst

Published in: SialoGlyco Chemistry and Biology II

Publisher: Springer International Publishing

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Abstract

Siglec-4, also known as myelin-associated glycoprotein (MAG), is a member of the siglec (sialic acid-binding immunoglobulin-like lectins) family. MAG binds with high preference to sialic acids α(2–3)-linked to D-galactose. Although the involvement and relevance of its sialic acid binding activity is still controversial, it could be demonstrated that interactions of MAG with sialylated gangliosides play an important role in axon stability and regeneration. In this article we describe in detail our current understanding of the biological role and the carbohydrate specificity of siglec-4. Furthermore, this review compiles the intensive research efforts leading from the identification of the minimal oligosaccharide binding epitope in gangliosides via micromolar oligosaccharide mimics to the development of small molecular weight and more drug-like sialic acid derivatives binding with low nanomolar affinities. Such compounds will be useful to elucidate MAG’s biological functions, which are currently not fully understood.

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Footnotes
1
The numbering of the amino acids was carried out according to [69]; see also Swiss-Prot entry P20916.
 
2
For recent reviews, see [9799].
 
Literature
2.
3.
go back to reference Crocker PR, Clark EA, Filbin MT, Gordon S, Jones Y, Kehrl JH, Kelm S, Le Douarin N, Powell L, Roder J, Schnaar RL, Sgroi DC, Stamenkovic K, Schauer R, Schachner M, van den Berg TK, van der Merwe PA, Watt SM, Varki A (1998) Glycobiology 8:v Crocker PR, Clark EA, Filbin MT, Gordon S, Jones Y, Kehrl JH, Kelm S, Le Douarin N, Powell L, Roder J, Schnaar RL, Sgroi DC, Stamenkovic K, Schauer R, Schachner M, van den Berg TK, van der Merwe PA, Watt SM, Varki A (1998) Glycobiology 8:v
4.
go back to reference Quarles RH, Everly JL, Brady RO (1972) Biochem Biophys Res Commun 47:491–497CrossRef Quarles RH, Everly JL, Brady RO (1972) Biochem Biophys Res Commun 47:491–497CrossRef
6.
go back to reference Sternberger NH, Quarles RH, Itoyama Y, Webster HD (1979) Proc Natl Acad Sci U S A 76:1510–1514CrossRef Sternberger NH, Quarles RH, Itoyama Y, Webster HD (1979) Proc Natl Acad Sci U S A 76:1510–1514CrossRef
7.
go back to reference Itoyama Y, Sternberger NH, Webster HD, Quarles RH, Cohen SR, Richardson EP (1980) Ann Neurol 7:167–177CrossRef Itoyama Y, Sternberger NH, Webster HD, Quarles RH, Cohen SR, Richardson EP (1980) Ann Neurol 7:167–177CrossRef
8.
go back to reference Kruse J, Mailhammer R, Wernecke H, Faissner A, Sommer I, Goridis C, Schachner M (1984) Nature 311:153–155CrossRef Kruse J, Mailhammer R, Wernecke H, Faissner A, Sommer I, Goridis C, Schachner M (1984) Nature 311:153–155CrossRef
10.
11.
go back to reference Poltorak M, Sadoul R, Keilhauer G, Landa C, Fahrig T, Schachner M (1987) J Cell Biol 105:1893–1899CrossRef Poltorak M, Sadoul R, Keilhauer G, Landa C, Fahrig T, Schachner M (1987) J Cell Biol 105:1893–1899CrossRef
12.
go back to reference Frail DE, Braun PE (1984) J Biol Chem 259:14857–14862 Frail DE, Braun PE (1984) J Biol Chem 259:14857–14862
13.
go back to reference Lai C, Brow MA, Nave KA, Noronha AB, Quarles RH, Bloom FE, Milner RJ, Sutcliffe JG (1987) Proc Natl Acad Sci U S A 84:4337–4341CrossRef Lai C, Brow MA, Nave KA, Noronha AB, Quarles RH, Bloom FE, Milner RJ, Sutcliffe JG (1987) Proc Natl Acad Sci U S A 84:4337–4341CrossRef
14.
15.
go back to reference Li C, Tropak MB, Gerlai R, Clapoff S, Abramow-Newerly W, Trapp B, Peterson A, Roder J (1994) Nature 369:747–750CrossRef Li C, Tropak MB, Gerlai R, Clapoff S, Abramow-Newerly W, Trapp B, Peterson A, Roder J (1994) Nature 369:747–750CrossRef
16.
go back to reference Montag D, Giese KP, Bartsch U, Martini R, Lang Y, Blüthmann H, Karthigasan J, Kirschner DA, Wintergerst ES, Nave KA (1994) Neuron 13:229–246CrossRef Montag D, Giese KP, Bartsch U, Martini R, Lang Y, Blüthmann H, Karthigasan J, Kirschner DA, Wintergerst ES, Nave KA (1994) Neuron 13:229–246CrossRef
17.
go back to reference Umemori H, Sato S, Yagi T, Aizawa S, Yamamoto T (1994) Nature 367:572–576CrossRef Umemori H, Sato S, Yagi T, Aizawa S, Yamamoto T (1994) Nature 367:572–576CrossRef
18.
go back to reference Kelm S, Pelz A, Schauer R, Filbin MT, Tang S, de Bellard M-E, Schnaar RL, Mahoney JA, Hartnell A, Bradfield P, Crocker PR (1994) Curr Biol 4:965–972CrossRef Kelm S, Pelz A, Schauer R, Filbin MT, Tang S, de Bellard M-E, Schnaar RL, Mahoney JA, Hartnell A, Bradfield P, Crocker PR (1994) Curr Biol 4:965–972CrossRef
19.
go back to reference McKerracher L, David S, Jackson DL, Kottis V, Dunn RJ, Braun PE (1994) Neuron 13:805–811CrossRef McKerracher L, David S, Jackson DL, Kottis V, Dunn RJ, Braun PE (1994) Neuron 13:805–811CrossRef
20.
go back to reference Mukhopadhyay G, Doherty P, Walsh FS, Crocker PR, Filbin MT (1994) Neuron 13:757–767CrossRef Mukhopadhyay G, Doherty P, Walsh FS, Crocker PR, Filbin MT (1994) Neuron 13:757–767CrossRef
22.
go back to reference Quarles RH, Barbarash GR, Figlewicz DA, McIntyre LJ (1983) Biochim Biophys Acta 757:140–143CrossRef Quarles RH, Barbarash GR, Figlewicz DA, McIntyre LJ (1983) Biochim Biophys Acta 757:140–143CrossRef
23.
26.
go back to reference May AP, Robinson RC, Vinson M, Crocker PR, Jones EY (1998) Mol Cell 1:719–728CrossRef May AP, Robinson RC, Vinson M, Crocker PR, Jones EY (1998) Mol Cell 1:719–728CrossRef
27.
go back to reference Strenge K, Schauer R, Bovin N, Hasegawa A, Ishida H, Kiso M, Kelm S (1998) Eur J Biochem 258:677–685CrossRef Strenge K, Schauer R, Bovin N, Hasegawa A, Ishida H, Kiso M, Kelm S (1998) Eur J Biochem 258:677–685CrossRef
28.
go back to reference Kelm S, Brossmer R, Isecke R, Gross H-J, Strenge K, Schauer R (1998) Eur J Biochem 255:663–672CrossRef Kelm S, Brossmer R, Isecke R, Gross H-J, Strenge K, Schauer R (1998) Eur J Biochem 255:663–672CrossRef
29.
go back to reference Kelm S, Schauer R, Manuguerra J-C, Gross H, Crocker PR (1994) Glycoconjugate J 11:576–585CrossRef Kelm S, Schauer R, Manuguerra J-C, Gross H, Crocker PR (1994) Glycoconjugate J 11:576–585CrossRef
30.
go back to reference Collins BE, Ito H, Sawada N, Ishida H, Kiso M, Schnaar RL (1999) J Biol Chem 274:37637–37643CrossRef Collins BE, Ito H, Sawada N, Ishida H, Kiso M, Schnaar RL (1999) J Biol Chem 274:37637–37643CrossRef
31.
go back to reference Collins BE, Yang LJS, Mukhopadhyay G, Filbin MT, Kiso M, Hasegawa A, Schnaar RL (1997) J Biol Chem 272:1248–1255CrossRef Collins BE, Yang LJS, Mukhopadhyay G, Filbin MT, Kiso M, Hasegawa A, Schnaar RL (1997) J Biol Chem 272:1248–1255CrossRef
32.
go back to reference Strenge K, Brossmer R, Ihrig P, Schauer R, Kelm S (2001) FEBS Lett 499:262–267CrossRef Strenge K, Brossmer R, Ihrig P, Schauer R, Kelm S (2001) FEBS Lett 499:262–267CrossRef
34.
go back to reference Vyas AA, Patel HV, Fromholt SE, Heffer-Lauc M, Vyas KA, Dang J, Schachner M, Schnaar RL (2002) Proc Natl Acad Sci U S A 99:8412–8417CrossRef Vyas AA, Patel HV, Fromholt SE, Heffer-Lauc M, Vyas KA, Dang J, Schachner M, Schnaar RL (2002) Proc Natl Acad Sci U S A 99:8412–8417CrossRef
35.
37.
go back to reference Cao Z, Gao Y, Deng K, Williams G, Doherty P, Walsh FS (2010) Mol Cell Neurosci 43:1–14CrossRef Cao Z, Gao Y, Deng K, Williams G, Doherty P, Walsh FS (2010) Mol Cell Neurosci 43:1–14CrossRef
38.
go back to reference Quarles RH (2007) J Neurochem 100:1431–1448 Quarles RH (2007) J Neurochem 100:1431–1448
40.
41.
go back to reference Yin X, Crawford TO, Griffin JW, Tu P-h, Lee VMY, Li C, Roder J, Trapp BD (1998) J Neurosci 18:1953–1962 Yin X, Crawford TO, Griffin JW, Tu P-h, Lee VMY, Li C, Roder J, Trapp BD (1998) J Neurosci 18:1953–1962
42.
go back to reference Mehta NR, Nguyen T, Bullen JW Jr, Griffin JW, Schnaar RL (2010) ACS Chem Neurosci 1:215–222CrossRef Mehta NR, Nguyen T, Bullen JW Jr, Griffin JW, Schnaar RL (2010) ACS Chem Neurosci 1:215–222CrossRef
43.
go back to reference Lopez PHH, Ahmad AS, Mehta NR, Toner M, Rowland EA, Zhang J, Doré S, Schnaar RL (2011) J Neurochem 116:900–908CrossRef Lopez PHH, Ahmad AS, Mehta NR, Toner M, Rowland EA, Zhang J, Doré S, Schnaar RL (2011) J Neurochem 116:900–908CrossRef
44.
go back to reference Mountney A, Zahner MR, Lorenzini I, Oudega M, Schramm LP, Schnaar RL (2010) Proc Natl Acad Sci U S A 107:11561–11566CrossRef Mountney A, Zahner MR, Lorenzini I, Oudega M, Schramm LP, Schnaar RL (2010) Proc Natl Acad Sci U S A 107:11561–11566CrossRef
45.
go back to reference Crocker PR, Kelm S, Hartnell A, Freeman S, Nath D, Vinson M, Mucklow S (1996) Biochem Soc Trans 24:150–156 Crocker PR, Kelm S, Hartnell A, Freeman S, Nath D, Vinson M, Mucklow S (1996) Biochem Soc Trans 24:150–156
47.
go back to reference Yang LJS, Zeller CB, Shaper NL, Kiso M, Hasegawa A, Shapiro RE, Schnaar RL (1996) Proc Natl Acad Sci U S A 93:814–818CrossRef Yang LJS, Zeller CB, Shaper NL, Kiso M, Hasegawa A, Shapiro RE, Schnaar RL (1996) Proc Natl Acad Sci U S A 93:814–818CrossRef
48.
go back to reference Collins BE, Kiso M, Hasegawa A, Tropak MB, Roder JC, Crocker PR, Schnaar RL (1997) J Biol Chem 272:16889–16895CrossRef Collins BE, Kiso M, Hasegawa A, Tropak MB, Roder JC, Crocker PR, Schnaar RL (1997) J Biol Chem 272:16889–16895CrossRef
49.
go back to reference Sheikh KA, Sun J, Liu Y, Kawai H, Crawford TO, Proia RL, Griffin JW, Schnaar RL (1999) Proc Natl Acad Sci U S A 96:7532–7537CrossRef Sheikh KA, Sun J, Liu Y, Kawai H, Crawford TO, Proia RL, Griffin JW, Schnaar RL (1999) Proc Natl Acad Sci U S A 96:7532–7537CrossRef
50.
go back to reference Ito H, Ishida H, Collins BE, Fromholt SE, Schnaar RL, Kiso M (2003) Carbohydr Res 338:1621–1639CrossRef Ito H, Ishida H, Collins BE, Fromholt SE, Schnaar RL, Kiso M (2003) Carbohydr Res 338:1621–1639CrossRef
51.
go back to reference Prabhanjan H, Kameyama A, Ishida H, Kiso M, Hasegawa A (1991) Carbohydr Res 220:127–143CrossRef Prabhanjan H, Kameyama A, Ishida H, Kiso M, Hasegawa A (1991) Carbohydr Res 220:127–143CrossRef
52.
go back to reference Prabhanjan H, Aoyama K, Kiso M, Hasegawa A (1992) Carbohydr Res 233:87–99CrossRef Prabhanjan H, Aoyama K, Kiso M, Hasegawa A (1992) Carbohydr Res 233:87–99CrossRef
53.
54.
go back to reference Ito H, Ishida H, Kiso M, Hasegawa A (1998) Carbohydr Res 306:581–585 Ito H, Ishida H, Kiso M, Hasegawa A (1998) Carbohydr Res 306:581–585
55.
go back to reference Sawada N, Ishida H, Collins BE, Schnaar RL, Kiso M (1999) Carbohydr Res 316:1–5CrossRef Sawada N, Ishida H, Collins BE, Schnaar RL, Kiso M (1999) Carbohydr Res 316:1–5CrossRef
56.
go back to reference Richardson PJ, Walker JH, Jones RT, Whittaker VP (1982) J Neurochem 38:1605–1614CrossRef Richardson PJ, Walker JH, Jones RT, Whittaker VP (1982) J Neurochem 38:1605–1614CrossRef
57.
go back to reference Hirabayashi Y, Nakao T, Irie F, Whittaker VP, Kon K, Ando S (1992) J Biol Chem 267:12973–12978 Hirabayashi Y, Nakao T, Irie F, Whittaker VP, Kon K, Ando S (1992) J Biol Chem 267:12973–12978
58.
go back to reference Bock N, Kelm S (2006) Binding and inhibition assay for siglecs. In: Brockhausen I (ed) Methods in molecular biology, vol 347. Humana, Totowa, pp 359–376 Bock N, Kelm S (2006) Binding and inhibition assay for siglecs. In: Brockhausen I (ed) Methods in molecular biology, vol 347. Humana, Totowa, pp 359–376
59.
go back to reference Blixt O, Collins BE, van den Nieuwenhof IM, Crocker PR, Paulson JC (2003) J Biol Chem 278:31007–31019CrossRef Blixt O, Collins BE, van den Nieuwenhof IM, Crocker PR, Paulson JC (2003) J Biol Chem 278:31007–31019CrossRef
60.
go back to reference Blixt O, Brown J, Schur MJ, Wakarchuk W, Paulson JC (2001) J Org Chem 66:2442–2448CrossRef Blixt O, Brown J, Schur MJ, Wakarchuk W, Paulson JC (2001) J Org Chem 66:2442–2448CrossRef
61.
go back to reference Blixt O, Allin K, Pereira L, Datta A, Paulson JC (2002) J Am Chem Soc 124:5739–5746CrossRef Blixt O, Allin K, Pereira L, Datta A, Paulson JC (2002) J Am Chem Soc 124:5739–5746CrossRef
63.
64.
go back to reference Lüning B, Norberg T, Rivera-Baeza C, Tejbrant J (1991) Glycoconjugate J 8:450–455CrossRef Lüning B, Norberg T, Rivera-Baeza C, Tejbrant J (1991) Glycoconjugate J 8:450–455CrossRef
65.
go back to reference Vyas AA, Blixt O, Paulson JC, Schnaar RL (2005) J Biol Chem 280:16305–16310CrossRef Vyas AA, Blixt O, Paulson JC, Schnaar RL (2005) J Biol Chem 280:16305–16310CrossRef
66.
go back to reference Bhunia A, Schwardt O, Gäthje H, Gao G-P, Kelm S, Benie AJ, Hricovini M, Peters T, Ernst B (2008) ChemBioChem 9:2941–2945CrossRef Bhunia A, Schwardt O, Gäthje H, Gao G-P, Kelm S, Benie AJ, Hricovini M, Peters T, Ernst B (2008) ChemBioChem 9:2941–2945CrossRef
67.
go back to reference Schwardt O, Gao G-P, Visekruna T, Rabbani S, Gassmann E, Ernst B (2004) J Carbohydr Chem 23:1–26CrossRef Schwardt O, Gao G-P, Visekruna T, Rabbani S, Gassmann E, Ernst B (2004) J Carbohydr Chem 23:1–26CrossRef
68.
go back to reference Shin S-Y, Gäthje H, Schwardt O, Gao G-P, Ernst B, Kelm S, Meyer B (2008) ChemBioChem 9:2946–2949CrossRef Shin S-Y, Gäthje H, Schwardt O, Gao G-P, Ernst B, Kelm S, Meyer B (2008) ChemBioChem 9:2946–2949CrossRef
69.
go back to reference Sato S, Fujita N, Kurihara T, Kuwano R, Kakahashi Y, Miyatake T (1989) Biochem Biophys Res Commun 163:1473–1480CrossRef Sato S, Fujita N, Kurihara T, Kuwano R, Kakahashi Y, Miyatake T (1989) Biochem Biophys Res Commun 163:1473–1480CrossRef
70.
go back to reference Schwardt O, Gäthje H, Vedani A, Mesch S, Gao G-P, Spreafico M, von Orelli J, Kelm S, Ernst B (2009) J Med Chem 52:989–1004CrossRef Schwardt O, Gäthje H, Vedani A, Mesch S, Gao G-P, Spreafico M, von Orelli J, Kelm S, Ernst B (2009) J Med Chem 52:989–1004CrossRef
71.
go back to reference Schwizer D, Gäthje H, Kelm S, Porro M, Schwardt O, Ernst B (2006) Bioorg Med Chem 14:4944–4957CrossRef Schwizer D, Gäthje H, Kelm S, Porro M, Schwardt O, Ernst B (2006) Bioorg Med Chem 14:4944–4957CrossRef
72.
go back to reference Kelm S, Brossmer R (2003) PCT patent WO 03/000709A2 Kelm S, Brossmer R (2003) PCT patent WO 03/000709A2
73.
go back to reference Shelke SV, Gao G-P, Mesch S, Gäthje H, Kelm S, Schwardt O, Ernst B (2007) Bioorg Med Chem 15:4951–4965CrossRef Shelke SV, Gao G-P, Mesch S, Gäthje H, Kelm S, Schwardt O, Ernst B (2007) Bioorg Med Chem 15:4951–4965CrossRef
74.
go back to reference Gao G, Smiesko M, Schwardt O, Gäthje H, Kelm S, Vedani A, Ernst B (2007) Bioorg Med Chem 15:7459–7469CrossRef Gao G, Smiesko M, Schwardt O, Gäthje H, Kelm S, Vedani A, Ernst B (2007) Bioorg Med Chem 15:7459–7469CrossRef
76.
80.
go back to reference Hansch C (1971) Quantitative structure-activity relationships in drug design. In: Ariens EJ (ed) Drug design, vol 1. Academic, New York, pp 271–342 Hansch C (1971) Quantitative structure-activity relationships in drug design. In: Ariens EJ (ed) Drug design, vol 1. Academic, New York, pp 271–342
81.
go back to reference Mesch S, Moser D, Strasser DS, Kelm A, Cutting B, Rossato G, Vedani A, Koliwer-Brandl H, Wittwer M, Rabbani S, Schwardt O, Kelm S, Ernst B (2010) J Med Chem 53:1597–1615CrossRef Mesch S, Moser D, Strasser DS, Kelm A, Cutting B, Rossato G, Vedani A, Koliwer-Brandl H, Wittwer M, Rabbani S, Schwardt O, Kelm S, Ernst B (2010) J Med Chem 53:1597–1615CrossRef
82.
go back to reference Mesch S, Lemme K, Koliwer-Brandl H, Strasser DS, Schwardt O, Kelm S, Ernst B (2010) Carbohydr Res 345:1348–1359CrossRef Mesch S, Lemme K, Koliwer-Brandl H, Strasser DS, Schwardt O, Kelm S, Ernst B (2010) Carbohydr Res 345:1348–1359CrossRef
83.
go back to reference Schwardt O, Koliwer-Brandl H, Zimmerli R, Mesch S, Rossato G, Spreafico M, Vedani A, Kelm S, Ernst B (2010) Bioorg Med Chem 18:7239–7251CrossRef Schwardt O, Koliwer-Brandl H, Zimmerli R, Mesch S, Rossato G, Spreafico M, Vedani A, Kelm S, Ernst B (2010) Bioorg Med Chem 18:7239–7251CrossRef
85.
86.
87.
go back to reference Markgren P-O, Schaal W, Hämäläinen M, Karlén A, Hallberg A, Samuelsson B, Danielson UH (2002) J Med Chem 45:5430–5439CrossRef Markgren P-O, Schaal W, Hämäläinen M, Karlén A, Hallberg A, Samuelsson B, Danielson UH (2002) J Med Chem 45:5430–5439CrossRef
88.
go back to reference Shuman CF, Hämäläinen MD, Danielson UH (2004) J Mol Recognit 17:106–119CrossRef Shuman CF, Hämäläinen MD, Danielson UH (2004) J Mol Recognit 17:106–119CrossRef
89.
90.
go back to reference Wild MK, Huang MC, Schulze-Horsel U, van der Merwe PA, Vestweber D (2001) J Biol Chem 276:31602–31612CrossRef Wild MK, Huang MC, Schulze-Horsel U, van der Merwe PA, Vestweber D (2001) J Biol Chem 276:31602–31612CrossRef
91.
go back to reference Herfurth L, Ernst B, Öhrlein R, Wagner B, Ricklin D, Strasser DS, Magnani JL, Benie AJ, Peters T (2005) J Med Chem 48:6879–6886CrossRef Herfurth L, Ernst B, Öhrlein R, Wagner B, Ricklin D, Strasser DS, Magnani JL, Benie AJ, Peters T (2005) J Med Chem 48:6879–6886CrossRef
92.
go back to reference Regan J, Pargellis CA, Cirillo PF, Gilmore T, Hickey ER, Peet GW, Proto A, Swinamer A, Moss N (2003) Bioorg Med Chem Lett 13:3101–3104CrossRef Regan J, Pargellis CA, Cirillo PF, Gilmore T, Hickey ER, Peet GW, Proto A, Swinamer A, Moss N (2003) Bioorg Med Chem Lett 13:3101–3104CrossRef
93.
go back to reference Kati WM, Montgomery D, Carrick R, Gubareva L, Maring C, McDaniel K, Steffy K, Molla A, Hayden F, Kempf D, Kohlbrenner W (2002) Antimicrob Agents Chemother 46:1014–1021CrossRef Kati WM, Montgomery D, Carrick R, Gubareva L, Maring C, McDaniel K, Steffy K, Molla A, Hayden F, Kempf D, Kohlbrenner W (2002) Antimicrob Agents Chemother 46:1014–1021CrossRef
96.
go back to reference Nagata K, Handa H (2000) Real-time analysis of biomolecular interactions: applications of Biacore. Springer, BerlinCrossRef Nagata K, Handa H (2000) Real-time analysis of biomolecular interactions: applications of Biacore. Springer, BerlinCrossRef
101.
go back to reference Shelke SV, Cutting B, Jiang X, Koliwer-Brandl H, Strasser DS, Schwardt O, Kelm S, Ernst B (2010) Angew Chem Int Ed 49:5721–5725CrossRef Shelke SV, Cutting B, Jiang X, Koliwer-Brandl H, Strasser DS, Schwardt O, Kelm S, Ernst B (2010) Angew Chem Int Ed 49:5721–5725CrossRef
102.
go back to reference Ernst B, Cutting B, Shelke SV (2006) PCT/WO2007/105094A1 Ernst B, Cutting B, Shelke SV (2006) PCT/WO2007/105094A1
104.
105.
go back to reference Jahnke W, Perez LB, Paris CG, Strauss A, Fendrich G, Nalin CM (2000) J Am Chem Soc 122:7394–7395CrossRef Jahnke W, Perez LB, Paris CG, Strauss A, Fendrich G, Nalin CM (2000) J Am Chem Soc 122:7394–7395CrossRef
106.
107.
go back to reference Vazquez J, Tautz L, Ryan JJ, Vuori K, Mustelin T, Pellecchia M (2007) J Med Chem 50:2137–2143CrossRef Vazquez J, Tautz L, Ryan JJ, Vuori K, Mustelin T, Pellecchia M (2007) J Med Chem 50:2137–2143CrossRef
108.
go back to reference Jain NU, Venot A, Umemoto K, Leffler H, Prestegard JH (2001) Protein Sci 10:2393–2400CrossRef Jain NU, Venot A, Umemoto K, Leffler H, Prestegard JH (2001) Protein Sci 10:2393–2400CrossRef
109.
go back to reference Bertini I, Fragai M, Lee Y-M, Luchinat C, Terni B (2004) Angew Chem Int Ed 43:2254–2256CrossRef Bertini I, Fragai M, Lee Y-M, Luchinat C, Terni B (2004) Angew Chem Int Ed 43:2254–2256CrossRef
110.
111.
go back to reference Lewis WG, Green LG, Grynszpan F, Radic Z, Carlier PR, Taylor P, Finn MG, Sharpless KB (2002) Angew Chem 114:1095–1099CrossRef Lewis WG, Green LG, Grynszpan F, Radic Z, Carlier PR, Taylor P, Finn MG, Sharpless KB (2002) Angew Chem 114:1095–1099CrossRef
112.
go back to reference Lewis WG, Green LG, Grynszpan F, Radic Z, Carlier PR, Taylor P, Finn MG, Sharpless KB (2002) Angew Chem Int Ed 41:1053–1057CrossRef Lewis WG, Green LG, Grynszpan F, Radic Z, Carlier PR, Taylor P, Finn MG, Sharpless KB (2002) Angew Chem Int Ed 41:1053–1057CrossRef
113.
go back to reference Manetsch R, Krasinski A, Radic Z, Raushel J, Taylor P, Sharpless KB, Kolb HC (2004) J Am Chem Soc 126:12809–12818CrossRef Manetsch R, Krasinski A, Radic Z, Raushel J, Taylor P, Sharpless KB, Kolb HC (2004) J Am Chem Soc 126:12809–12818CrossRef
114.
go back to reference Mocharla VP, Colasson B, Lee LV, Roeper S, Sharpless KB, Wong C-H, Kolb HC (2004) Angew Chem 116:118–122CrossRef Mocharla VP, Colasson B, Lee LV, Roeper S, Sharpless KB, Wong C-H, Kolb HC (2004) Angew Chem 116:118–122CrossRef
115.
go back to reference Mocharla VP, Colasson B, Lee LV, Roeper S, Sharpless KB, Wong C-H, Kolb HC (2005) Angew Chem Int Ed 44:116–120CrossRef Mocharla VP, Colasson B, Lee LV, Roeper S, Sharpless KB, Wong C-H, Kolb HC (2005) Angew Chem Int Ed 44:116–120CrossRef
116.
go back to reference Krasinski A, Radic Z, Manetsch R, Raushel J, Taylor P, Sharpless KB, Kolb HC (2005) J Am Chem Soc 127:6686–6692CrossRef Krasinski A, Radic Z, Manetsch R, Raushel J, Taylor P, Sharpless KB, Kolb HC (2005) J Am Chem Soc 127:6686–6692CrossRef
117.
go back to reference Whiting M, Muldoon J, Lin Y-C, Silverman SM, Lindstrom W, Olson AJ, Kolb HC, Finn MG, Sharpless KB, Elder JH, Fokin VV (2006) Angew Chem 118:1463–1467CrossRef Whiting M, Muldoon J, Lin Y-C, Silverman SM, Lindstrom W, Olson AJ, Kolb HC, Finn MG, Sharpless KB, Elder JH, Fokin VV (2006) Angew Chem 118:1463–1467CrossRef
118.
go back to reference Whiting M, Muldoon J, Lin Y-C, Silverman SM, Lindstrom W, Olson AJ, Kolb HC, Finn MG, Sharpless KB, Elder JH, Fokin VV (2006) Angew Chem Int Ed 46:1435–1439CrossRef Whiting M, Muldoon J, Lin Y-C, Silverman SM, Lindstrom W, Olson AJ, Kolb HC, Finn MG, Sharpless KB, Elder JH, Fokin VV (2006) Angew Chem Int Ed 46:1435–1439CrossRef
Metadata
Title
SIGLEC-4 (MAG) Antagonists: From the Natural Carbohydrate Epitope to Glycomimetics
Authors
Oliver Schwardt
Soerge Kelm
Beat Ernst
Copyright Year
2015
DOI
https://doi.org/10.1007/128_2013_498