Journal of Organic Chemistry 2001-05-04

Chemoenzymatic synthesis of neoglycopeptides: application to an alpha-Gal-terminated neoglycopeptide.

D Ramos, P Rollin, W Klaffke

Index: J. Org. Chem. 66 , 2948-56, (2001)

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Abstract

A novel methodology for the enzymatic preparation from suitably derivatized oligosaccharides of N-linked neoglycopeptides using the microbial glutaminyl-peptide gamma-glutamyl transferase, transglutaminase (TGase), is described. N-Allyl glycosides of various oligosaccharides were photochemically coupled with cysteamine to yield amino-terminated thioether spacers, which were accepted by transglutaminase to transamidate the side-chain gamma-carboxamide group in the dipeptide Z-Gln-Gly.