Synthesis of the Antimicrobial S-Linked Glycopeptide, Glycocin F

被引：26

作者：

Brimble, Margaret A. ^{[1
,2
]}

Edwards, Pat J. ^{[3
]}

Harris, Paul W. R. ^{[1
,2
]}

Norris, Gillian E. ^{[3
]}

Patchett, Mark L. ^{[3
]}

Wright, Tom H. ^{[1
,2
]}

Yang, Sung-Hyun ^{[1
]}

Carley, Sarah E. ^{[1
]}

机构：

[1] Univ Auckland, Sch Chem Sci, Auckland 1142, New Zealand

[2] Univ Auckland, Sch Biol Sci, Maurice Wilkins Ctr Mol Biodiscovery, Auckland 1142, New Zealand

[3] Massey Univ, Inst Fundamental Sci, Palmerston North 4442, New Zealand

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 09期

关键词：

antimicrobial peptides; disulfide; glycocinF; glycopeptides; glycosylation; NATIVE CHEMICAL LIGATION; SOLID-PHASE SYNTHESIS; AMINO-ACIDS; PEPTIDES; EPIMERIZATION; DERIVATIVES; MECHANISM; PROTEINS; STRATEGY; GLYCOSYL;

D O I：

10.1002/chem.201405692

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of glycocinF, a uniquely diglycosylated antimicrobial peptide bearing a rare S-linked N-acetylglucosamine (GlcNAc) moiety in addition to an O-linked GlcNAc, has been accomplished using a native chemical ligation strategy. The synthetic and naturally occurring peptides were compared by HPLC, mass spectrometry, NMR and CD spectroscopy, and their stability towards chymotrypsin digestion and antimicrobial activity were measured. This is the first comprehensive structural and functional comparison of a naturally occurring glycocin with an active synthetic analogue.

引用

页码：3556 / 3561

页数：6

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