3 years ago

Genomics-Driven Discovery of Chlorinated Cyclic Hexapeptides Ulleungmycins A and B from a Streptomyces Species

Genomics-Driven Discovery of Chlorinated Cyclic Hexapeptides Ulleungmycins A and B from a Streptomyces Species
Jong Seog Ahn, Mina Jang, Bo Yeon Kim, Sung-Kyun Ko, Young-Soo Hong, Kyung Taek Heo, In-Ja Ryoo, Jae-Hyuk Jang, Sangkeun Son, Won-Gon Kim, Jong-Won Kim, Jun-Pil Jang, Byeongsan Lee
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.

Publisher URL: http://dx.doi.org/10.1021/acs.jnatprod.7b00660

DOI: 10.1021/acs.jnatprod.7b00660

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