Synthesis of L-glycero-D-manno-heptopyranose-containing oligosaccharide structures found in lipopolysaccharides from Haemophilus influenzae

被引：12

作者：

Bernlind, C ^{[1
]}

Oscarson, S ^{[1
]}

机构：

[1] UNIV STOCKHOLM,ARRHENIUS LAB,DEPT ORGAN CHEM,S-10691 STOCKHOLM,SWEDEN

来源：

CARBOHYDRATE RESEARCH | 1997年 / 297卷 / 03期

基金：

瑞典研究理事会;

关键词：

carbohydrates; oligosaccharide synthesis; bacterial antigens; lipopolysaccharide; heptopyranose;

D O I：

10.1016/S0008-6215(96)00275-3

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：

Syntheses are described of the tetrasaccharide 2-(4-trifluoroacetamidophenyl)ethyl O-(beta-D-galactopyranosyl)-(1 --> 2)-O-(L-glycero-alpha-D-manno-heptopyranosyl)-(1 --> 2)-O-(L-glycero-alpha-D--manno-heptopyranosyl)-(1 --> 3)-L-glycero-alpha-D-mnnno-heptopyranoside (20) and the three trisaccharides 2-(4-trifluoroacetamidophenyl)ethyl O-(L-glycero-alpha-D-manno-heptopyranosyl)-(1 --> 2)-O-(L-glycero-alpha-D-manno-heptopyranosl)-(1 --> 3)-L-glycero-alpha-D-manno-heptopyranoside(17), 2-(4-trifluoroacetamidophenyl)ethyl O-(beta-D-glucopyranosyl)-(1 --> 4)-O-(beta-D-glucopyranosyl)-(1 --> 4)-L-glycero-alpha-D-manno-heptopyranoside (5), and 2-(4-trifluoroacetamidophenyl)ethyl O-(beta-D-galactopyranosyl)-(1 --> 4)-O-(beta-D-glucopyranosyl)-(1 --> 4)-L-glycero-alpha-D-manno-heptopyranoside (8), corresponding to structures found in the lipooligosaccharides of Haemophilus influenzae. (C) 1997 Elsevier Science Ltd.

引用

页码：251 / 260

页数：10

共 21 条

[1]

BERNLIND C, 1996, THESIS STOCKHOLM U

[2] SYNTHESIS OF LD-HEPP AND KDO CONTAINING DISACCHARIDE AND TETRASACCHARIDE DERIVATIVES OF NEISSERIA-MENINGITIDIS INNER-CORE REGION VIA IODONIUM ION PROMOTED GLYCOSIDATIONS [J].

BOONS, GJPH ;

VANDELFT, FL ;

VANDERKLEIN, PAM ;

VANDERMAREL, GA ;

VANBOOM, JH .

TETRAHEDRON, 1992, 48 (05) :885-904

[3] A NOVEL PROMOTER FOR THE EFFICIENT CONSTRUCTION OF 1,2-TRANS LINKAGES IN GLYCOSIDE SYNTHESIS, USING THIOGLYCOSIDES AS GLYCOSYL DONORS [J].

FUGEDI, P ;

GAREGG, PJ .

CARBOHYDRATE RESEARCH, 1986, 149 (01) :C9-C12

[4] SYNTHESIS OF METHYL 3-O-(ALPHA-D-GLUCOPYRANOSYL)-7-O-(L-GLYCERO-ALPHA-D-MANNO-HEPTOPYRANOSYL)-L-GLYCERO-ALPHA-D-MANNO-HEPTOPYRANOSIDE [J].

GAREGG, PJ ;

OSCARSON, S ;

SZONYI, M .

CARBOHYDRATE RESEARCH, 1990, 205 :125-132

[5] STUDIES ON KOENIGS-KNORR GLYCOSIDATIONS [J].

GAREGG, PJ ;

KONRADSSON, P ;

KVARNSTROM, I ;

NORBERG, T ;

SVENSSON, SCT ;

WIGILIUS, B .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1985, 39 (07) :569-577

[6]

GAREGG PJ, 1992, CARBOHYD RES, V228, P121

[7] CHEMISTRY OF GLYCOSIDIC LINKAGE - EFFICIENT SYNTHESIS OF 1,2-TRANS-DISACCHARIDES [J].

HANESSIAN, S ;

BANOUB, J .

CARBOHYDRATE RESEARCH, 1977, 53 (01) :C13-C16

[8] THE DESIGN AND SYNTHESIS OF ANTIBODY-BINDING SITE PROBES - 3 PENTASACCHARIDE ANALOGS OF THE BRUCELLA-A ANTIGEN PREPARED BY ACTIVATION INSITU OF THIOGLYCOSIDES WITH BROMINE [J].

KIHLBERG, J ;

EICHLER, E ;

BUNDLE, DR .

CARBOHYDRATE RESEARCH, 1991, 211 (01) :59-75

[9] CARBOHYDRATE THIO ORTHO ESTERS - SYNTHESIS AND CHARACTERIZATION [J].

MAGNUSSON, G .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (26) :4110-4112

[10]

MASKELL DJ, 1992, MOL MICROBIOL, V6, P3052

← 1 2 3 →