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

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Genomics-Driven Discovery of Chlorinated Cyclic Hexapeptides Ulleungmycins A and B from a Streptomyces Species
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-10-30 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00660
Sangkeun Son _{1,

2} , Young-Soo Hong _{1,

2} , Mina Jang _{1,

2} , Kyung Taek Heo _{1,

2} , Byeongsan Lee ₁ , Jun-Pil Jang ₁ , Jong-Won Kim ₁ , In-Ja Ryoo ₁ , Won-Gon Kim _{2,

3} , Sung-Kyun Ko _{1,

2} , Bo Yeon Kim _{1,

2} , Jae-Hyuk Jang _{1,

2} , Jong Seog Ahn _{1,

2}

Affiliation

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.

中文翻译：

基因组学驱动的链霉菌属物种中的氯化环六肽Ulleungmycins A和B的发现。

链霉菌（Streptomyces sp。）的基因组序列分析。KCB13F003显示存在一个编码黄素依赖性卤化酶和非核糖体肽合成酶的隐性基因簇。使用多种培养基的多效性方法，再用LC-MS指导的分离和光谱分析，可以鉴定出两种新的氯化环六肽，乌来霉素A和B（1和2）。它们的结构（包括绝对构型）通过1D和2D NMR技术，先进的Marfey分析和GITC衍生化确定。新的肽，具有不常见的氨基酸5-氯-1-色氨酸和d-高丝氨酸对革兰氏阳性病原菌（包括耐甲氧西林和耐喹诺酮的金黄色葡萄球菌）表现出中等的抗菌活性。

更新日期：2017-10-30

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