Identification and Proposed Relative and Absolute Configurations of Niphimycins C-E from the Marine-Derived Streptomyces sp. IMB7-145 by Genomic Analysis

Journal of Natural Products
Yuanyuan HuMaoluo Gan

Abstract

Analysis of the whole genome sequence of Streptomyces sp. IMB7-145 revealed the presence of seven type I polyketide synthase biosynthetic gene clusters, one of which was highly homologous to the biosynthetic gene cluster of azalomycin F. Detailed bioinformatic analysis of the modular organization of the PKS gene suggested that this gene is responsible for niphimycin biosynthesis. Guided by genomic analysis, a large-scale cultivation ultimately led to the discovery and characterization of four new niphimycin congeners, namely, niphimycins C-E (1-3) and 17-O-methylniphimycin (4). The configurations of most stereocenters of niphimycins have not been determined to date. In the present study, the relative configurations were elucidated by spectroscopic analysis, including J-based analysis and the CNMR database method. Further, the full absolute configurations of niphimycins were completely proposed for the first time based on biosynthetic gene cluster analysis of the ketoreductase and enoylreductase domains for hydroxy- and methyl-bearing stereocenters. Compounds 1, 3, 4, and niphimycin Iα (5) showed antimicrobial activity against methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci (MIC: 8-64 μg/mL), as ...Continue Reading

References

Mar 24, 2000·Science·E W MyersJ C Venter
Jul 18, 2001·Journal of the American Chemical Society·A B BenowitzY Kishi
Jul 10, 2003·Chembiochem : a European Journal of Chemical Biology·Patrick Caffrey
Apr 9, 2005·The Journal of Antibiotics·János Bérdy
Aug 28, 2007·Chemistry & Biology·Adrian T Keatinge-Clay
Nov 28, 2008·Clinical Infectious Diseases : an Official Publication of the Infectious Diseases Society of America·Helen W BoucherJohn Bartlett
May 8, 2009·Genome Research·Ruiqiang LiJun Wang
Jun 11, 2009·Angewandte Chemie·Christian Hertweck
Nov 30, 2010·Current Opinion in Chemical Biology·Jaclyn M WinterChristian Hertweck
Mar 30, 2011·Proceedings of the National Academy of Sciences of the United States of America·Luisa LauretiBertrand Aigle
Apr 9, 2011·Nature·Matthew A Cooper, David Shlaes
Nov 15, 2011·Chembiochem : a European Journal of Chemical Biology·Marie E YurkovichPeter F Leadlay
Apr 21, 2012·Angewandte Chemie·Keishi IshidaChristian Hertweck
Apr 25, 2012·Magnetic Resonance in Chemistry : MRC·Tomasz LaskowskiJan Pawlak
Jul 17, 2012·Microbiological Research·Ramesh Subramani, William Aalbersberg
Aug 21, 2013·Microbiological Research·Panchanathan ManivasaganSe-Kwon Kim
Nov 13, 2013·Angewandte Chemie·Hui HongPeter F Leadlay
May 23, 2014·Angewandte Chemie·Olaf Hartmann, Markus Kalesse
Jun 22, 2014·BMC Bioinformatics·Marten Boetzer, Walter Pirovano
Nov 22, 2014·Nucleic Acids Research·Aron Marchler-BauerStephen H Bryant
May 8, 2015·Nucleic Acids Research·Tilmann WeberMarnix H Medema
Nov 7, 2015·Genomics, Proteomics & Bioinformatics·Anthony Rhoads, Kin Fai Au
Jun 9, 2016·Natural Product Reports·Nadine ZiemertTilmann Weber
Nov 11, 2016·Beilstein Journal of Organic Chemistry·Hui HongPeter F Leadlay

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Citations

Jun 30, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jing WangLinzhuan Wu
Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Feb 23, 2020·Microorganisms·Adriana RegoCatarina Magalhães
Aug 7, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jiao LiMaoluo Gan
Jul 22, 2020·Archives of Pharmacal Research·Cong WangShugeng Cao
Nov 2, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xiaoyuan SongSheng Cao
Feb 6, 2020·International Journal of Molecular Sciences·Ganjun YuanZezhang Tom Wen
Oct 7, 2020·Natural Product Reports·Roberto G S BerlinckIgor D Jurberg
Dec 13, 2019·Organic Letters·Jiao LiMaoluo Gan

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