Synthesis and identification in bacterial lipopolysaccharides of 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto- and -D-glycero-D-talo-non-2-ulosonic acids

被引:55
作者
Tsvetkov, YE
Shashkov, AS
Knirel, YA
Zähringer, U
机构
[1] Russian Acad Sci, ND Zelinskii Inst Organ Chem, Moscow 117913, Russia
[2] Forschungszentrum Borstel, Zentrum Med & Biowissensch, D-23845 Borstel, Germany
基金
俄罗斯基础研究基金会;
关键词
5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acid; synthesis; legionaminic acid; identification of; lipopolysaccharide components; Legionella pneumophila;
D O I
10.1016/S0008-6215(01)00041-6
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
5,7-Diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto- and -D-glycero-D-talo-non-2-ulosonic acids were synthesized by condensation of 2,4-diacetamido-2,4,6-trideoxy-D-mannose with oxalacetic acid. Comparison of the H-1 and C-13 NMR data and the specific optical rotation values of these monosaccharides and the corresponding L-glycero-D-galacto and L-glycero-D-talo isomers synthesized earlier [Tsvetkov, Y. E.; Shashkov, A. S.; Knirel, Y. A.; Backinowsky, L. V.; Zahringer, U. Mendelera Commun. 2000, 90-92] with data of the natural compounds enabled the identification in bacterial lipopolysaccharides of derivatives of 5,7-diamino-3,5,7,9-tetradeoxy-D-glycerogalacto-non-2-ulosonic (legionaminic) acid and epimers of legionaminic acid at C-4 and C-8. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:233 / 237
页数:5
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