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Diversity of Polyketide Chains Achieved by Deleting the Tailoring Genes in the Biosynthesis of Ansatrienins
Author(s) -
Wang Jianxiong,
Li Xiaoman,
Lu Chunhua,
Shen Yuemao
Publication year - 2018
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201700528
Subject(s) - biosynthesis , polyketide , gene cluster , stereochemistry , genbank , gene , accession number (library science) , hydroxylation , strain (injury) , polyketide synthase , mutant , chemistry , streptomyces , biochemistry , biology , genetics , enzyme , bacteria , anatomy
The ast gene cluster (GenBank accession numbers KF813023.1 and KP284551) was characterized to be responsible for the biosynthesis of ansatrienins in Streptomyces sp. XZQH13, which contains astC , astF1 , and astF2 genes involved in the assembly of the N ‐cyclohexanoyl d ‐alanyl side chain and the hydroxylation of C‐19, respectively. Further to investigating the biosynthetic mechanism of ansatrienins, herein we constructed the mutant strains XZQH13OEΔ astF2 and XZQH13OEΔ astC Δ astF2 . Three new ansatrienin analogues, namely, ansatrienols I–K ( 1 – 3 ), along with trienomycinol ( 4 ) and 3‐ O ‐demethyltrienomycinol ( 5 ), were isolated from the XZQH13OEΔ astC Δ astF2 strain, and trienomycin A ( 6 ) and trienomycin G ( 7 ) were isolated from the XZQH13OEΔ astF2 strain. Their structures were determined by a combination of high‐resolution MS (ESI) and 1D and 2D NMR spectroscopy. Accordingly, a pathway for the biosynthesis of these new ansatrienins was proposed.