Isolation and Structure Determination of New Antibacterial Peptide Curacomycin Based on Genome Mining. Issue 12 (17th October 2017)

• Record Type: Journal Article
• Authors: Kaweewan, Issara; Komaki, Hisayuki; Hemmi, Hikaru; Kodani, Shinya
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 12(2017)
• Page Start: 1838
• Page End: 1844
• Publication Date: 2017-10-17
• Subjects: amino acids -- genome mining -- peptides -- streptomyces -- structure elucidation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700433
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: 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. Abstract : Sweet Child O′ Mining : A new antibacterial cyclic peptide, named curacomycin, and its analogue dechlorocuracomycin were isolated based on genome mining. The biosynthetic pathways for these peptides were proposed by analysis of biosynthetic gene clusters that were found in the genome sequences.