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

被引:24
作者
Bengtsson, M
Broddefalk, J
Dahmén, J
Henriksson, K
Kihlberg, J
Lönn, H
Srinivasa, BR
Stenvall, K
机构
[1] Astro Draco AB, Preclin R&D, S-22100 Lund, Sweden
[2] Umea Univ, S-90187 Umea, Sweden
[3] Astra Res Ctr India, Bangalore 560003, Karnataka, India
关键词
glycopeptide; synthesis; T cell; immune response;
D O I
10.1023/A:1006988810800
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
The 2-bromoethyl beta-glycosides of the disaccharide galabiose [Gal(alpha 1-4) Gal] and the trisaccharides globotriose [Gal(alpha 1-4)Gal(beta 1-4)Glc] and 3'-sialyllactose [Neu5Ac(alpha 2-3)Gal(beta 1-4)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. H-1 NMR spectroscopy revealed that beta-elimination and epimerization of neoglycopeptide stereocentres did not occur during the synthesis.
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页码:223 / 231
页数:9
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