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

Autor: Bengtsson, Marita, Broddefalk, Johan, Dahmen, Jan, Henriksson, Krister, Kihlberg, Jan, Lonn, Hans, Srinivasa, B.R., Stenvall, Kristina
Zdroj: Glycoconjugate Journal; Mar1998, Vol. 15 Issue 3, p223-231, 9p
Abstrakt: 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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index