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通过将2-溴乙基糖苷与T细胞刺激肽中的半胱氨酸和高半胱氨酸残基偶联来进行新糖肽的汇聚合成。

Convergent synthesis of neoglycopeptides by coupling of 2-bromoethyl glycosides to cysteine and homocysteine residues in T cell stimulating peptides.

作者信息

Bengtsson M, Broddefalk J, Dahmén J, Henriksson K, Kihlberg J, Lönn H, Srinivasa B R, Stenvall K

机构信息

Astra Draco AB, Preclinical R&D, Lund, Sweden.

出版信息

Glycoconj J. 1998 Mar;15(3):223-31. doi: 10.1023/a:1006988810800.

DOI:10.1023/a:1006988810800
PMID:9579799
Abstract

The 2-bromoethyl beta-glycosides of the disaccharide galabiose [Gal(alpha1-4)Gal] and the trisaccharides globotriose [Gal(alpha1-4)Gal(beta1-4)Glc] and 3'-sialyllactose [Neu5Ac(alpha2-3)Gal(beta1-4)Glc] have been prepared by improved routes. The 2-bromoethyl glycosides were then used in cesium carbonate promoted alkylations of the sulfhydryl groups of cysteine and homocysteine residues in T cell stimulating peptides. This convergent and general approach was used to prepare 16 neoglycopeptides which were obtained in 52-95% yields after purification by HPLC. 1H NMR spectroscopy revealed that beta-elimination and epimerization of neoglycopeptide stereocentres did not occur during the synthesis.

摘要

通过改进的路线制备了二糖半乳糖（Gal(α1-4)Gal）、三糖球三糖（Gal(α1-4)Gal(β1-4)Glc）和3'-唾液酸乳糖（Neu5Ac(α2-3)Gal(β1-4)Glc）的2-溴乙基β-糖苷。然后将2-溴乙基糖苷用于碳酸铯促进的T细胞刺激肽中半胱氨酸和高半胱氨酸残基巯基的烷基化反应。采用这种收敛性通用方法制备了16种新糖肽，经高效液相色谱纯化后，产率为52-95%。核磁共振氢谱显示，在合成过程中，新糖肽立体中心未发生β-消除和差向异构化。

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