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Isolation and Structure Determination of New Antibacterial Peptide Curacomycin Based on Genome Mining
Author(s) -
Kaweewan Issara,
Komaki Hisayuki,
Hemmi Hikaru,
Kodani Shinya
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700433
Subject(s) - chemistry , valine , peptide , isoleucine , antimicrobial , genome , streptomyces , stereochemistry , gene cluster , leucine , combinatorial chemistry , gene , amino acid , bacteria , biochemistry , organic chemistry , genetics , biology
A new antibacterial cyclic peptide, named curacomycin ( 1 ), and its analogue dechlorocuracomycin ( 2 ) were isolated from Streptomyces curacoi (NBRC 12761 T ) and Streptomyces noursei (NBRC 15452 T ), respectively, by using genome mining. The chemical structures of these two peptides were determined by using a combination of MS (ESI) and NMR spectroscopy. The structure of compound 1 was determined to be a cyclic peptide that consisted of six amino acids, including: valine (Val), leucine (Leu), isoleucine (Ile), ornithine (Orn), β‐hydroxyasparagine (OHAsn), and 5‐chlorotryptophan (ClTrp). The NMR data of compound 2 were very similar to that of compound 1 , which indicated that the structure of compound 2 was a dechlorinated analogue of compound 1 . A comparison of the antimicrobial activities of these two peptides indicated that the presence of chlorine in compound 1 was critical for its antimicrobial activity. The proposed biosynthetic gene clusters for compounds 1 and 2 were found in the genome data of S. curacoi and S. noursei , respectively. The functions of the biosynthetic genes were considered by comparison of the two gene clusters.