Using Chemical Synthesis to Probe Structure-Activity Relationships of the Glycoactive Bacteriocin Glycocin F

被引：23
作者：
Bisset, Sean W. [1 ,2 ]
Yang, Sung-Hyun [3 ]
Amso, Zaid [3 ]
Harris, Paul W. R. [2 ,3 ]
Patchett, Mark L. [1 ]
Brimble, Margaret A. [2 ,3 ]
Norris, Gillian E. [1 ,2 ]
机构：
[1] Massey Univ, Inst Fundamental Sci, Colombo Rd, Palmerston North 4442, New Zealand
[2] Univ Auckland, Maurice Wilkins Ctr Mol Biodiscovery, Private Bag 92019, Auckland, New Zealand
[3] Univ Auckland, Sch Chem Sci, 23 Symonds St, Auckland 1142, New Zealand
来源：
ACS CHEMICAL BIOLOGY | 2018年 / 13卷 / 05期
关键词：
S-LINKED GLYCOPEPTIDE; LACTOBACILLUS-PLANTARUM; PHOSPHOTRANSFERASE SYSTEM; GLYCOSYLATED BACTERIOCIN; ANTIMICROBIAL ACTIVITY; SUBLANCIN; 168; NMR STRUCTURE; ENTEROCIN; 96; PEPTIDE; PHOSPHORYLATION;
D O I：
10.1021/acschembio.8b00055
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Glycocin F, a bacteriocin produced by Lactobacillus plantarum KW30, is glycosylated with two N-acetyl-D-glucosamine sugars, and has been shown to exhibit a rapid and reversible bacteriostasis on susceptible cells. The roles of certain structural features of glycocin F have not been studied to date. We report here the synthesis of various glycocin F analogues through solid-phase peptide synthesis (SPPS) and native chemical ligation (NCL), allowing us to probe the roles of different structural features of this peptide. Our results indicate that the bacteriostatic activity of glycocin F is controlled by the glycosylated interhelical loop, while the glycosylated flexible tail appears to be involved in localizing the peptide to its cellular target.
引用
收藏
页码：1270 / 1278
页数：9
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