Substitution of the GalNAc-α-O-Thr11 residue in drosocin with O-linked glyco-peptoid residue: Effect on antibacterial activity and conformational change

被引：12

作者：

Ahn, Mija ^{[3
]}

Murugan, Ravichandran N. ^{[3
]}

Nan, Yong Hai ^{[1
,2
]}

Cheong, Chaejoon ^{[3
]}

Sohn, Holk ^{[4
]}

Kim, Eun-Hee ^{[3
]}

Hwang, Eunha ^{[3
]}

Ryu, Eun Kyoung ^{[3
]}

Kang, Shin Won ^{[5
]}

Shin, Song Yub ^{[1
,2
]}

Bang, Jeong Kyu ^{[3
]}

机构：

[1] Chosun Univ, Dept Biomat, Grad Sch, Kwangju 501759, South Korea

[2] Chosun Univ, Sch Med, Dept Cellular & Mol Med, Kwangju 501759, South Korea

[3] Korea Basic Sci Inst, Div Magnet Resonance, Ochang 363883, Chung Buk, South Korea

[4] Univ Texas Austin, Coll Nat Sci, Dept Chem & Biochem, Austin, TX 78712 USA

[5] Pusan Natl Univ, Dept Chem, Pusan 609735, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 20期

关键词：

Glyco-peptoid; Antibacterial peptide; Drosocin; Structure-activity relationship (SAR); PEPTIDE; DROSOPHILA; ANALOGS; NMR;

D O I：

10.1016/j.bmcl.2011.08.012

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

One of the obvious disadvantages of natural peptides is their liability to proteases. Among the several solutions for this issue, peptoids or oligomers of N-substituted glycine have emerged as a promising tool that may enhance the stability of proteolysis-susceptible natural peptides. We have synthesized the drosocin and its glyco-peptoid analogues linked O-GalNAc at the Thr(11) residue. One of our glyco-peptoid analogues showed an increased antibacterial activity by the modification of the Thr(11) residue with glycopeptoid. Structure-activity relationship studies revealed that the antibacterial activity by glyco-peptoid drosocin requires three key elements: free hydroxyl group on the carbohydrate moiety, gamma-methyl group of the Thr(11) residue derivative and (S)-configuration over (R)-configuration. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6148 / 6153

页数：6

共 13 条

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