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[从铜绿假单胞菌免疫型7的脂多糖中鉴定3-脒基-2-乙酰氨基-2,3-二脱氧-L-古洛糖醛酸]

[Identification of 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid in lipopolysaccharide from Pseudomonas aeruginosa immunotype 7].

作者信息

Knirel' Iu A, Paramonov N A, Vinogradov E V, Shashkov A S, Kochetkov N K

出版信息

Bioorg Khim. 1986 Jul;12(7):992-4.

PMID:2429670
Abstract

O-Specific polysaccharide chain of Pseudomonas aeruginosa immunotype 7 lipopolysaccharide is composed of 3-acetamidino-2-acetamido-2,3-dideoxy-L-guluronic acid (GulNAcAmA), 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid (ManN2Ac2A), and N-acetyl-D-fucosamine (FucNAc). On solvolysis with anhydrous hydrogen fluoride, the polysaccharide afforded a trisaccharide containing all its components. Borohydride reduction of the trisaccharide in boric acid solution resulted in conversion of reducing fucosamine into fucosaminitol, whereas in water the reduction was accompanied by reductive deamination of acetamidino function into ethylamino group. On hydrolysis with aqueous triethylamine, acetamidino group gave acetamido group. Analysis of the trisaccharides thus obtained by 1H NMR spectroscopy (including nuclear Overhauser effect), 13C NMR spectroscopy, and fast-atom bombardment mass spectrometry allowed the determination of the structure of the unusual uronic acid derivative and the following structure of the polysaccharide repeating unit: -4)-alpha-L-GulNAcAmA-(1-4)-beta-D-ManN2Ac2A-(1-3)-alpha-D-+ ++FucNAc-(1-.

摘要

铜绿假单胞菌免疫型7脂多糖的O-特异性多糖链由3-脒基-2-乙酰氨基-2,3-二脱氧-L-古洛糖醛酸(GulNAcAmA)、2,3-二乙酰氨基-2,3-二脱氧-D-甘露糖醛酸(ManN2Ac2A)和N-乙酰-D-岩藻糖胺(FucNAc)组成。用无水氟化氢进行溶剂解时,该多糖得到了一种包含其所有组分的三糖。在硼酸溶液中对该三糖进行硼氢化还原,导致还原性岩藻糖胺转化为岩藻糖胺醇,而在水中进行还原时,脒基会伴随着还原脱氨基反应转化为乙氨基。用三乙胺水溶液水解时,脒基会转化为乙酰氨基。通过1H NMR光谱(包括核Overhauser效应)、13C NMR光谱和快原子轰击质谱对由此得到的三糖进行分析,从而确定了这种不寻常的糖醛酸衍生物的结构以及多糖重复单元的以下结构:-4)-α-L-GulNAcAmA-(1-4)-β-D-ManN2Ac2A-(1-3)-α-D-+ ++FucNAc-(1- 。

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