Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Solid-Phase O-Glycosylation with a Glucosamine Derivative for the Synthesis of a Glycopeptide

Philip Ryan A B C , Andy Hsien Wei Koh D , Anna Elizabeth Lohning D and Santosh Rudrawar A B C E F
+ Author Affiliations
- Author Affiliations

A Menzies Health Institute Queensland, Griffith University, Gold Coast, Qld 4222, Australia.

B School of Pharmacy and Pharmacology, Griffith University, Gold Coast, Qld 4222, Australia.

C School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia.

D Faculty of Health Sciences and Medicine, Bond University, Robina, Qld 4229, Australia.

E Quality Use of Medicines Network, Gold Coast, Qld 4222, Australia.

F Corresponding author. Email: s.rudrawar@griffith.edu.au

Australian Journal of Chemistry - https://doi.org/10.1071/CH17201
Submitted: 10 April 2017  Accepted: 16 June 2017   Published online: 20 July 2017

Abstract

An efficient synthesis of the O-linked glycosylamino acid Fmoc–l-Ser((Ac)3–β-d-GlcNAc)-OH building block is described. The utility of the method was demonstrated with direct solid-phase O-glycosylation of the hydroxyl group on the amino acid (Ser) side chain of a human α-A crystallin-derived peptide (AIPVSREEK) in nearly quantitative glycosylation yield.


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