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Application of the trichloroacetimidate method to the synthesis of glycopeptides of the mucin type containing a β-d-Galp-(1→3)-d-GalpNAc unit

✍ Scribed by Willy Kinzy; Richard R. Schmidt

Book ID
102992333
Publisher
Elsevier Science
Year
1987
Tongue
English
Weight
846 KB
Volume
164
Category
Article
ISSN
0008-6215

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✦ Synopsis

Mucin-type O-glycopeptides containing the &D-Gab-( l-+3)-o-G@NAc disaccharide core unit, which is also the T-antigenic determinant, were synthesized from o-galactose, 2-azido-%deoxy-o-galactose, 2-azido-2-deoxylactose, and L-serine precursors by applying the trichloroacetimidate method. Thus, fi-~-Gal~?-(1+3)a-D-GalpNAc-( l-3)-Ser (1) and B-D-Gal_@( l-+/%~-GlcpNAc-( 1-6)~[P-D-Galp-(l-3)]-cw-o-GalpNAc-(1+3)-Ser (2) were obtained. A protected precursor of 2 having free OH groups at C-4 and C-6 of the inner sugar unit is a valuable intermediate for the synthesis of further O-glycopeptides of this core-unit type. * Dedicated to Burckhardt Helferich in commemoration of the hundredth anniversary of his birth. + Glycosylimidates, part 24. For part 23, see ref. 1.

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