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

Philip Ryan; Andy Hsien Wei Koh; Anna Elizabeth Lohning; Santosh Rudrawar

doi:10.1071/CH17201

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

Philip Ryan
, Andy Hsien Wei Koh
, Anna Elizabeth Lohning
, Santosh Rudrawar^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Research › peer-review

5 Citations (Scopus)

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 A crystallin-derived peptide (AIPVSREEK) in nearly quantitative glycosylation yield.

Original language	English
Pages (from-to)	1151-1157
Number of pages	7
Journal	Australian Journal of Chemistry
Volume	70
Issue number	10
DOIs	https://doi.org/10.1071/CH17201
Publication status	Published - 2017

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10.1071/CH17201

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title = "Solid-Phase O-Glycosylation with a Glucosamine Derivative for the Synthesis of a Glycopeptide",

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 A crystallin-derived peptide (AIPVSREEK) in nearly quantitative glycosylation yield.",

author = "Philip Ryan and Koh, \{Andy Hsien Wei\} and Lohning, \{Anna Elizabeth\} and Santosh Rudrawar",

year = "2017",

doi = "10.1071/CH17201",

language = "English",

volume = "70",

pages = "1151--1157",

journal = "Australian Journal of Chemistry",

issn = "0004-9425",

publisher = "CSIRO",

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T1 - Solid-Phase O-Glycosylation with a Glucosamine Derivative for the Synthesis of a Glycopeptide

AU - Ryan, Philip

AU - Koh, Andy Hsien Wei

AU - Lohning, Anna Elizabeth

AU - Rudrawar, Santosh

PY - 2017

Y1 - 2017

N2 - 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 A crystallin-derived peptide (AIPVSREEK) in nearly quantitative glycosylation yield.

AB - 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 A crystallin-derived peptide (AIPVSREEK) in nearly quantitative glycosylation yield.

UR - https://www.scopus.com/pages/publications/85030227747

U2 - 10.1071/CH17201

DO - 10.1071/CH17201

M3 - Article

AN - SCOPUS:85030227747

SN - 0004-9425

VL - 70

SP - 1151

EP - 1157

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 10

ER -

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

Abstract

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