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2016 | OriginalPaper | Buchkapitel

3. N-glycosides

verfasst von : Marco Brito-Arias

Erschienen in: Synthesis and Characterization of Glycosides

Verlag: Springer International Publishing

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Abstract

N-glycosides are generated when a sugar component is attached to an aglycon, through a nitrogen atom, establishing as a result a C–N–C linkage. Nucleosides are among the most relevant N-glycosides since they are essential components of DNA, RNA, cofactors, and a variety of antiviral and antineoplastic drugs.

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Vorheriges Kapitel O-glycoside Formation

Nächstes Kapitel Nucleoside Mimetics

Nishimura S (1982) Minor components in transfer RNA: their characterization, location, and function. Prog Res Mol Biol 12:49–85CrossRef

Kondo T, Ohgi T, Goto T (1977) Synthesis of 5-methyltubercidin and its α-anomer via condensation of the anion of 4-methoxy-5-methyl-2-methylthiopyrrolo [2, 3-d] pyrimidine and 2, 3, 5-tri-O-benzyl-D-ribofuranosyl Bromide. Agric Biol Chem 41:1501–1507

Akimoto H, Imayima E, Hitaka T, Nomura H, Nishimura S (1988) Synthesis of queuine, the base of naturally occurring hypermodified nucleoside (queuosine), and its analogues. J Chem Soc Perkin 1 1637–1644

Barnett CJ, Grubb LM (2000) Total synthesis of Q Base (Queuine). Tetrahedron 56:9221–9225CrossRef

Itaya T (1990) Synthesis of 7-methyl-3-β-D-ribofuranosylwye, the putative structure for the hypermodified nucleoside isolated from archaebacterial transfer ribonucleic acids. Chem Pharm Bull 38:2656–2661CrossRef

Knapp S (1995) Synthesis of complex nucleoside antibiotics. Chem Rev 95:1859–1876CrossRef

Migawa MT, Risen LM, Griffey RH, Swayze EE (2005) An efficient synthesis of gougerotin and related analogues using solid- and solution-phase methodology. Org Lett 7:3429–3432CrossRef

Chida N, Koizumi K, Kitada Y, Yokohama C, Ogawa S (1994) Total synthesis of (+)-polyoxin J starting from myo-inositol. J Chem Soc Chem Commun 111–113

Maguire MP, Feldman PL, Rapoport H (1990) Stereoselective synthesis and absolute stereochemistry of sinefungin. J Org Chem 55:948–955CrossRef

10.

Kalvoda L, Prystas M, Sorm F (1976) Synthesis of exotoxin produced by Bacillus thuringiensis. I. Formation of the ethereal bond between ribose and glucose. Collect Czech Chem Commun 41:788–799CrossRef

11.

Myers AG, Gin DY, Rogers DH (1994) Synthetic studies of the tunicamycin antibiotics. Preparation of (+)-tunicaminyluracil, (+)-tunicamycin-V, and 5′-epitunicamycin-V. J Am Chem Soc 116:4697–4718CrossRef

12.

Hahn H, Heitsch H, Rathmann R, Zimmermann G, Bormann C, Zahner H, Konig W (1987) Partialsynthese der Nikkomycine Bx und Kx sowie unnatürlicher Stereoisomerer und Strukturanaloga (Partial synthesis of nikkomycins Bx, Kx and unnatural stereoisomers and structural analogs). Liebigs Ann Chem 1987:803–807CrossRef

13.

Hanessian S, Kloss J, Sugawara T (1986) Stereocontrolled access to the octosyl acids: total synthesis of octosyl acid A. J Am Chem Soc 108:2758CrossRef

14.

Ikemoto N, Schreiber SL (1992) Total synthesis of (-)-hikizimycin employing the strategy of two-directional chain synthesis. J Am Chem Soc 114:2524–2536CrossRef

15.

Knapp S, Nandan SR (1994) Synthesis of capuramycin. J Org Chem 59:281–283CrossRef

16.

Blackburn GM, Gait M (1990) Nucleic acids in chemistry and biology. IRL, Oxford

17.

Blaisdell TP, Lee S, Kasaplar P, Sun X, Tan KL (2013) Practical silyl protection of ribonucleosides. Org Lett 15:4710–4713CrossRef

18.

Ferrero M, Gotor V (2000) Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides. Chem Rev 100:4319–4348CrossRef

19.

Wong CH, Chen ST, Hennen WJ, Bibbs JA, Wang YF, Liu JLC, Pantoliano MW, Whitlo M, Bryan PN (1990) Enzymes in organic synthesis: use of subtilisin and a highly stable mutant derived from multiple site-specific mutations. J Am Chem Soc 112:945–953CrossRef

20.

de la Cruz A, Elguero J, Gotor V, Goya P, Martínez A, Moris F (1991) Lipase-mediated acylation of acyclonucleosides. Application to novel fluoroquinolone derivatives. Synth Commun 21:1477–1480CrossRef

21.

Gotor V, Morís F (1992) Regioselective acylation of 2′-deoxynucleosides through an enzymatic reaction with oxime esters. Synthesis 1992:626–628CrossRef

22.

Ozaki S, Yamashita K, Konishi T, Maekawa T, Eshima M, Uemura A, Ling L (1995) Enzyme aided regioselective acylation of nucleosides. Nucleosides Nucleotides 14:401–404CrossRef

23.

Singh HK, Cote GL, Sikirski RS (1993) Enzymatic regioselective deacylation of 2′,3′,5′-tri-o-acylribonucleosides - enzymatic-synthesis of 2′,3′-di-o-acylribonucleosides. Tetrahedron Lett 34:5201–5204CrossRef

24.

Damkjaer DI, Petersen M, Wengel J (1994) Lipase catalyzed diastereoselective deacetylations of anomeric mixtures of peracetylated 2′-deoxynucleosides. Nucleosides Nucleotides 13:1801–1807CrossRef

25.

Kawana M (1981) The reactions of benzylated pyrrole and adenine ribonucleosides with Grignard reagents. Chem Lett 10:1541–1542CrossRef

26.

Kozai S, Fuzikawa T, Harumoto K, Maruyama T (2003) Introduction of a benzyl group onto the 2′-OH of 6-chloropurine 3′-O-benzoylriboside. Nucleosides Nucleotides Nucleic Acids 22:779–781CrossRef

27.

Serebryany V, Beigelman L (2002) An efficient preparation of protected ribonucleosides for phosphoramidite RNA synthesis. Tetrahedron Lett 43:1983–1985CrossRef

28.

Taniguchi T, Ogasawara K (1988) Extremely facile and selective nickel-catalyzed allyl ether cleavage. Angew Chem Int Ed 37:1136–1137CrossRef

29.

Robins MJ, Samano V, Johnson MD (1990) Nucleic acid-related compounds. 58. Periodinane oxidation, selective primary deprotection, and remarkably stereoselective reduction of tert-butyldimethylsilyl-protected ribonucleosides. Synthesis of 9-(.beta.-D-xylofuranosyl)adenine or 3′-deuterioadenosine from adenosine. J Org Chem 55:410–412CrossRef

30.

Kondo T, Ohgi T, Goto T (1983) Synthesis of Q base (queuine). Chem Lett 12:419–422CrossRef

31.

Battacharya BK, Rao TS, Revankar GR (1995) Total synthesis of 2′-deoxy-2′-arafluoro-tubercidin, 2′-deoxy-2′-arafluoro-toyocamycin, 2′-deoxy-2′-arafluoro-sangivamycin and certain related nucleosides. J Chem Soc Perkin 1 1543–1550

32.

Seela F, Steker H, Driller H, Bindig U (1987) 2-Amino-2′-desoxytubercidin und verwandte Pyrrolo[2,3-d]pyrimidinyl-2′-desoxyribofuranoside. Liebigs Ann Chem 1987:15–19CrossRef

33.

Seela F, Kehne A (1983) Desoxytubercidin - Synthese eines 2-Desoxyadenosin-Isosteren durch Phasentransferglykosylierung. Liebigs Ann Chem 1983:876–884CrossRef

34.

Kazimierczuk Z, Cottam HB, Revankar GR, Robins RK (1984) Synthesis of 2′-deoxytubercidin, 2′-deoxyadenosine, and related 2′-deoxynucleosides via a novel direct stereospecific sodium salt glycosylation procedure. J Am Chem Soc 106:6379–6382CrossRef

35.

Edstrom E, Wei Y (1995) A new synthetic route to β-2′-deoxyribosyl-5-substituted pyrrolo[2,3-d]pyrimidines. Synthesis of 2′-deoxycadeguomycin. J Org Chem 60:5069–5076CrossRef

36.

Davoll J, Lythgoe B, Todd AR (1948) 185. Experiments on the synthesis of purine nucleosides. Part XIX. A synthesis of adenosine. J Chem Soc 967–969

37.

Montgomery JA, Thomas HL (1962) Purine nucleosides. Adv Carbohydr Chem 17:301–369

38.

Tipson RS (1939) A note on the action of silver salts of organic acids on bromoacetyl sugars. a new form of tetraacetyl l-rhamnose. J Biol Chem 130:55–59

39.

Jung KH, Schmidt RR (1988) Synthese von N-Ethylguanosin-5′-carboxamid. Liebigs Ann Chem 1988:1013–1014CrossRef

40.

De Clercq E, Gosselin G, Bergogne MC, De Ruddes J, Imbach JL (1987) Systematic synthesis and biological evaluation of alpha- and beta-D-lyxofuranosyl nucleosides of the five naturally occurring nucleic acid bases. J Med Chem 30:982–991CrossRef

41.

Hilbert GE, Johnson TB (1930) Researches on pyrimidines. CXVII. A method for the synthesis of nucleosides. J Am Chem Soc 52:4489–4494CrossRef

42.

Vorbrüggen H, Krolikiewicz K, Bennua B (1981) Nucleoside syntheses, (XXII1) Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts. Chem Ber 114:1234–1255CrossRef

43.

Vorbrüggen H, Höfle G (1981) Nucleoside syntheses, (XXIII1) On the mechanism of nucleoside synthesis. Chem Ber 114:1256–1268CrossRef

44.

Wang P, Chun B-K, Rachakonda S, Du J, Khan N, Shi J, Stec W, Cleary D, Ross BS, Sofia MJ (2009) An efficient and diastereoselective synthesis of PSI-6130: a clinically efficacious inhibitor of HCV NS5B Polymerase. J Org Chem 74:6819–6824CrossRef

45.

Fukuyama K, Ohrui H, Kuwahara S (2015) Synthesis of EFdA via a diastereoselective aldol reaction of a protected 3-keto furanose. Org Lett 17:828–831CrossRef

46.

Kageyama M, Nagasawa T, Yoshida M, Ohrui H, Kuwahara S (2011) Enantioselective total synthesis of the potent anti-HIV nucleoside EfdA. Org Lett 13(13):5264–5266CrossRef

47.

Maier S, Preuss R, Schmidt RR (1990) Synthesis of the ezomycin A basic structure. Liebigs Ann Chem 1990:483–489CrossRef

48.

Liao J, Sun J, Yu B (2009) An improved procedure for nucleoside synthesis using glycosyl trifluoroacetimidates as donors. Carbohydr Res 344:1034–1038CrossRef

49.

Mitsunobu O (1981) The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 1981:1–28CrossRef

50.

Marminon C, Pierré A, Pfeiffer B, Pérez V, Léonce S, Joubert A, Bailly C, Renard P, Hickman J, Prudhomme M (2003) Syntheses and antiproliferative activities of 7-azarebeccamycin analogues bearing one 7-azaindole moiety. J Med Chem 46:609–622CrossRef

51.

Heck RF (1982) Palladium-catalyzed vinylation of organic halides. Org React 27:345–390

52.

Miyaura NM, Suzuki A (1995) Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 95:2457–2483CrossRef

53.

Scott WJ, Crisp GT, Stille JK (1984) Palladium-catalyzed coupling of vinyl triflates with organostannanes. A short synthesis of pleraplysillin-1. J Am Chem Soc 106:4630–4632CrossRef

54.

Negishi EI (2002) A genealogy of Pd-catalyzed cross-coupling. J Organomet Chem 653:30–40CrossRef

55.

Sonogashira K (1991) Coupling reactions between sp2 and sp carbon centers. Comprehens Org Chem 3:521–549

56.

Hatanaka Y, Hiyama T (1991) Highly selective cross-coupling reactions of organosilicon compounds mediated by fluoride ion and a palladium catalyst. Synlett 1991:845–853CrossRef

57.

Trost BM, Van Vranken DL (1996) Asymmetric transition metal-catalyzed allylic alkylations. Chem Rev 96:395–422CrossRef

58.

Tsuji J, Yamakawa T (1979) A convenient method for the preparation of 1-olefins by the palladium catalyzed hydrogenolysis of allylic acetates and allylic phenyl ethers with ammonium formate. Tetrahedron Lett 20:613–616CrossRef

59.

Ruth JL, Bergstrom DE (1978) C-5 substituted pyrimidine nucleosides. 1. Synthesis of C-5 allyl, propyl, and propenyl uracil and cytosine nucleosides via organopalladium intermediates. J Org Chem 43:2870–2876CrossRef

60.

Bergstrom DE, Ruth JL (1976) Synthesis of C-5 substituted pyrimidine nucleosides via organopalladium intermediates. J Am Chem Soc 98:1587–1589CrossRef

61.

Bergstrom DE, Ruth JL, Warwick P (1981) C-5-Substituted pyrimidine nucleosides. 3. Reaction of allylic chlorides, alcohols, and acetates with pyrimidine nucleoside derived organopalladium intermediates. J Org Chem 46:1432–1441CrossRef

62.

Agrofolio LA, Gillaizeau I, Saito Y (2003) Palladium-assisted routes to nucleosides. Chem Rev 103:1875–1916CrossRef

63.

Ji L, Xiang S-H, Leng W-L, Hoang KLM, Liu X-W (2015) Palladium-catalyzed glycosylation: novel synthetic approach to diverse N-heterocyclic glycosides. Org Lett 17:1357–1360CrossRef

64.

Nie S, Li W, Yu B (2014) Total synthesis of nucleoside antibiotic A201A. J Am Chem Soc 136:4157–4160CrossRef

65.

Li J, Yu B (2015) A modular approach to the total synthesis of tunicamycins. Angew Chem Int Ed 54:6618–6621CrossRef

66.

Gross A, Abril O, Lewis JM, Geresh S, Whitesides GM (1983) Practical synthesis of 5-phospho-D-ribosyl alpha-1-pyrophosphate (PRPP): enzymatic routes from ribose 5-phosphate or ribose. J Am Chem Soc 105:7428–7435CrossRef

67.

Timmons SC, Hui JP, Pearson JL, Peltier P, Daniellou R, Nugier-Chauvin C, Soo EC, Syvitski RT, Ferrieres V, Jakeman DL (2008) Enzyme-catalyzed synthesis of furanosyl nucleotides. Org Lett 10:161–163CrossRef

68.

Eckstein F (ed) (1991) Oligonucleotides and analogs- a practical approach. IRL Press, Oxford University Press, New York, NY

69.

Li NS, Piccirilli JA (2004) Synthesis of the phosphoramidite derivatives of 2¢ Deoxy-2¢-C-a-methylcytidine and 2′-Deoxy-2′-C-a-hydroxymethylcytidine: analogues for chemical dissection of RNA′s 2¢-hydroxyl group. J Org Chem 69:4751–4959CrossRef

70.

Ohkubo A, Seio K, Sekine M (2004) A new strategy for the synthesis of oligodeoxynucleotides directed towards perfect O-selective internucleotidic bond formation without base protection. Tetrahedron Lett 45:363–366CrossRef

71.

Ohkubo A, Kuwayama Y, Nishino Y, Tsunoda H, Seio K, Sekine M (2010) Oligonucleotide synthesis involving deprotection of amidine-type protecting groups for nucleobases under acidic conditions. Org Lett 12:2496–2499CrossRef

72.

Dai Q, Saikia M, Li N-S, Pan T, Piccirilli JA (2009) Efficient chemical synthesis of AppDNA by adenylation of immobilized DNA-5′-monophosphate. Org Lett 11:1067–1070CrossRef

73.

Zlatev I, Lavergne T, Debart F, Vasseur J-J, Manoharan M, Morvan F (2010) Efficient solid-phase chemical synthesis of 5′-triphosphates of DNA, RNA, and their analogues. Org Lett 12:2190–2193CrossRef

74.

De Mesmaeker A, Haner R, Martin P, Moser HE (1995) Antisense oligonucleotides. Acc Chem Res 28:366–374CrossRef

75.

Damha MJ, Giannaris PA, Marfey PA, Reid LS (1991) Oligodeoxynucleotides containing unnatural L-2′-deoxyribose. Tetrahedon Lett 32:2573–2576CrossRef

76.

Sekine M, Tsuruoka H, Iimura S, Kusuoku H, Wada T (1996) Studies on steric and electronic control of 2′-3′ phosphoryl migration in 2′-phosphorylated uridine derivatives and its application to the synthesis of 2′-phosphorylated oligouridylates. J Org Chem 61:4087–4100CrossRef

77.

Mitsuya H, Yarchoan R, Broder S (1990) Molecular targets for AIDS therapy. Science 249:1533–1544CrossRef

78.

Dempcy R, Browne KA, Bruice TC (1995) Synthesis of the polycationic thymidyl DNG, its fidelity in binding polyanionic DNA/RNA and the stability and nature of the hybrid complexes. J Am Chem Soc 117:6140–6141CrossRef

79.

Oka N, Kondo T, Fujiwara S, Maizuru Y, Wada T (2009) Stereocontrolled synthesis of oligoribonucleoside phosphorothioates by an oxazaphospholidine approach. Org Lett 11:967–970CrossRef

80.

Barton DHR, McCombie SW (1975) A new method for the deoxygenation of secondary alcohols. J Chem Soc Perkin 1 1574–1585

Titel: N-glycosides
verfasst von: Marco Brito-Arias
Verlag: Springer International Publishing
Buch: Synthesis and Characterization of Glycosides
Print ISBN: 978-3-319-32308-4

Electronic ISBN: 978-3-319-32310-7

Copyright-Jahr: 2016
DOI: https://doi.org/10.1007/978-3-319-32310-7_3

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