126740-79-2Relevant academic research and scientific papers
SYNTHESIS OF GLYCOPEPTIDES OF THE MUCIN TYPE CONTAINING A β-D-GlcpNAc-(1->3)-D-GalpNAc UNIT
Kinzy, Willy,Schmidt, Richard R.
, p. 33 - 48 (2007/10/02)
Mucin-type O-glycopeptides containing the β-D-GlcpNAc-(1->3)-D-GalpNAc core unit were synthesised from 2-azido-2-deoxy-D-glucose, 2-azido-2-deoxy-D-galactose, 2-azido-2-deoxylactose, and L-serine precursors, using the trichloroacetimidate method.Thus, β-D-GlcpNAc-(1->3)-α-D-GalpNAc-(1->3)-Ser (1) and a derivative of β-D-Galp-(1->4)-β-D-GlcpNAc-(1->6)-3)>-α-D-GalpNAc-(1->3)-Ser (2) were obtained.A precursor of 1 having HO-4,6 of the 2-azido-2-deoxy-D-galactose residue unsubstituted was a valuable intermediate for the synthesis of 2 due to regioselective glycosylation at O-6.Regioselectivity in this reaction was not observed for precursors having a tert-butyldimethylsilyl group at O-1 instead of a protected L-serine moiety.
