Chemoenzymatic synthesis of the sialyl-α-(2→3′)-lactosamine trisaccharide with a 3-aminopropyl group as a spacer at the reducing end

被引：11

作者：

Choudhury, I ^{[1
]}

Minoura, N ^{[1
]}

Uzawa, H ^{[1
]}

机构：

[1] Natl Inst Adv Ind Sci & Technol, Lab Adv Bioelect, Tsukuba, Ibaraki 3058565, Japan

来源：

CARBOHYDRATE RESEARCH | 2003年 / 338卷 / 12期

关键词：

lactosamine; sialic acid; trisaccharide; chemoenzymatic;

D O I：

10.1016/S0008-6215(03)00167-8

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The trisaccharide, 3-aminopropyl 5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto -2-nonulopyranosylonic acid-(2 --> 3)-beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside has been synthesized chemoenzymatically for the first time. First, the acceptor, 3-aminopropyl beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside was synthesized in a conventional chemical manner, and then it was coupled with CMP-sialic acid using alpha-(2 --> 3)-(N)-sialyltransferase to afford the desired trisaccharide by an enzymatically stereocontrolled manner. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1265 / 1270

页数：6

共 21 条

[1] Chemical diversity in the sialic acids and related α-keto acids:: An evolutionary perspective [J].

Angata, T ;

Varki, A .

CHEMICAL REVIEWS, 2002, 102 (02) :439-469

[2] DIVERSITY OF OLIGOSACCHARIDE STRUCTURES LINKED TO ASPARAGINES OF THE SCRAPIE PRION PROTEIN [J].

ENDO, T ;

GROTH, D ;

PRUSINER, SB ;

KOBATA, A .

BIOCHEMISTRY, 1989, 28 (21) :8380-8388

[3] A NOVEL AND EFFICIENT SYNTHESIS OF NEOLACTO SERIES GANGLIOSIDES 3'-NLM(1) AND 6'NLM(1) [J].

GAUDINO, JJ ;

PAULSON, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :1149-1150

[4]

Grundler G., 1984, LIEBIGS ANN CHEM, V11, P1826

[5] Microbial glycosyltransferases for carbohydrate synthesis:: α-2,3-sialyltransferase from Neisseria gonorrheae [J].

Izumi, M ;

Shen, GJ ;

Wacowich-Sgarbi, S ;

Nakatani, T ;

Plettenburg, O ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10909-10918

[6] Biochemical engineering of the N-acyl side chain of sialic acid:: biological implications [J].

Keppler, OT ;

Horstkorte, R ;

Pawlita, M ;

Schmidts, C ;

Reutter, W .

GLYCOBIOLOGY, 2001, 11 (02) :11R-18R

[7] GLYCOSYLIMIDATES .24. APPLICATION OF THE TRICHLOROACETIMIDATE METHOD TO THE SYNTHESIS OF GLYCOPEPTIDES OF THE MUCIN TYPE CONTAINING A BETA-D-GALP-(1-]3)-D-GALPNAC UNIT [J].

KINZY, W ;

SCHMIDT, RR .

CARBOHYDRATE RESEARCH, 1987, 164 :265-276

[8]

Limberg G, 1996, LIEBIGS ANN-RECL, P1773

[9] Generation of molecular diversity on N-acetyllactosamine via O-cyanomethyl ethers [J].

Malet, C ;

Hindsgaul, O .

CARBOHYDRATE RESEARCH, 1997, 303 (01) :51-65

[10] A NOVEL STEREOSELECTIVE SYNTHESIS OF N-ACETYL-ALPHA-NEURAMINOSYL-GALACTOSE DISACCHARIDE DERIVATIVES, USING ANOMERIC S-GLYCOSYL XANTHATES [J].

MARRA, A ;

SINAY, P .

CARBOHYDRATE RESEARCH, 1990, 195 (02) :303-308

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