ISSN:
1573-4986
Keywords:
glycopeptide
;
synthesis
;
T cell
;
immune response
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract The 2-bromoethyl β-glycosides of the disaccharide galabiose [Gal(α1-4)Gal] and the trisaccharides globotriose [Gal(α1-4)Gal(β1-4)Glc] and 3′-sialyllactose [Neu5Ac(α2-3)Gal(β1-4)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 β-elimination and epimerization of neoglycopeptide stereocentres did not occur during the synthesis.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1006988810800
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