4.2 Article

Synthesis and reactivity of the monosaccharide esters of amino acids as models of teichoic acid fragment

期刊

GLYCOCONJUGATE JOURNAL
卷 17, 期 5, 页码 273-282

出版社

SPRINGER
DOI: 10.1023/A:1007157018792

关键词

monosaccharide; amino acid; ester; glycation; teichoic acid; Gram-positive bacteria

向作者/读者索取更多资源

The increasing prevalence of sepsis from Gram-positive bacterial pathogens necessitates further evaluation of the basic assumptions about the molecular pathogenesis of septic shock. Since diverse physiological functions of Gram-positive bacteria are controlled by the degree of esterification of teichoic acids with D-alanine, we examined the reactivity of monosaccharide esters in which anomerically free or protected D-glucose is linked through its C-6 hydroxy group to either phenylalanyl or tyrosyl residues as models for teichoic acid fragment. We show that the attached sugar moiety induces activation of the amino acid residue. Due to the enhanced reactivity of the NH2 group in the monosaccharide esters studied, the formation of products generated by intramolecular and intermolecular glycation reactions is accelerated resulting in heterogeneous mixture of compounds. These findings suggest that, if similar adducts are formed by glycation of D-alanine in teichoic acid of Gram-positive bacteria, they should be examined as potential bioactive ligands or chemical message for infection.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.2
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

暂无数据
暂无数据