Genomics-driven discovery of chlorinated cyclic hexapeptides ulleungmycins A and B from a Streptomyces species

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Title
Genomics-driven discovery of chlorinated cyclic hexapeptides ulleungmycins A and B from a Streptomyces species
Author(s)
Sangkeun Son; Young-Soo Hong; Mina Jang; Kyung Taek Heo; Byeongsan Lee; Jun-Pil Jang; Jong Won Kim; In Ja RyooWon Gon KimSung-Kyun KoBo Yeon KimJae-Hyuk JangJong Seog Ahn
Bibliographic Citation
Journal of Natural Products, vol. 80, no. 11, pp. 3025-3031
Publication Year
2017
Abstract
Analysis of the genome sequence of Streptomyces sp. KCB13F003 showed the presence of a cryptic gene cluster encoding flavin-dependent halogenase and nonribosomal peptide synthetase. Pleiotropic approaches using multiple culture media followed by LC-MS-guided isolation and spectroscopic analysis enabled the identification of two new chlorinated cyclic hexapeptides, ulleungmycins A and B (1 and 2). Their structures, including absolute configurations, were determined by 1D and 2D NMR techniques, advanced Marfey's analysis, and GITC derivatization. The new peptides, featuring unusual amino acids 5-chloro-l-tryptophan and d-homoleucine, exhibited moderate antibacterial activities against Gram-positive pathogenic bacteria including methicillin-resistant and quinolone-resistant Staphylococcus aureus.
ISSN
0163-3864
Publisher
Amer Chem Soc
DOI
http://dx.doi.org/10.1021/acs.jnatprod.7b00660
Type
Article
Appears in Collections:
Ochang Branch Institute > Anticancer Agent Research Center > 1. Journal Articles
Division of Research on National Challenges > Infectious Disease Research Center > 1. Journal Articles
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