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Unique post-translational oxime formation in the biosynthesis of the azolemycin complex of novel ribosomal peptides from Streptomyces sp. FXJ1.264

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Li, Ning, Song, Lijiang, Liu, Minghao, Shang, Fei, Anderson, Zoe, Fox, David J., Challis, Gregory L. and Huang, Yingping (2015) Unique post-translational oxime formation in the biosynthesis of the azolemycin complex of novel ribosomal peptides from Streptomyces sp. FXJ1.264. Chemical Science, 7 (1). pp. 482-488. doi:10.1039/c5sc03021h ISSN 2041-6520.

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Official URL: http://dx.doi.org/10.1039/C5SC03021H

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Abstract

Streptomycetes are a rich source of bioactive specialized metabolites, including several examples of the rapidly growing class of ribosomally-biosynthesized and post-translationally-modified peptide (RiPP) natural products. Here we report the discovery from Streptomyces sp. FXJ1.264 of azolemycins A–D, a complex of novel linear azole-containing peptides incorporating a unique oxime functional group. Bioinformatics analysis of the Streptomyces sp. FXJ1.264 draft genome sequence identified a cluster of genes that was hypothesized to be responsible for elaboration of the azolemycins from a ribosomally-biosynthesized precursor. Inactivation of genes within this cluster abolished azolemycin production, consistent with this hypothesis. Moreover, mutants lacking the azmE and azmF genes accumulated azolemycin derivatives lacking the O-methyl groups and an amino group in place of the N-terminal oxime (as well as proteolysed derivatives), respectively. Thus AzmE, a putative S-adenosyl methionine-dependent methyl transferase, is responsible for late-stage O-methylation reactions in azolemycin biosynthesis and AzmF, a putative flavin-dependent monooxygenase, catalyzes oxidation of the N-terminal amino group in an azolemycin precursor to the corresponding oxime. To the best of our knowledge, oxime formation is a hitherto unknown posttranslational modification in RiPP biosynthesis.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Q Science > QP Physiology
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH): Metabolites , Peptides , Peptides--Synthesis
Journal or Publication Title: Chemical Science
Publisher: Royal Society of Chemistry
ISSN: 2041-6520
Official Date: 5 October 2015
Dates:
DateEvent
2016UNSPECIFIED
5 October 2015Accepted
14 October 2015Submitted
Volume: 7
Number: 1
Page Range: pp. 482-488
DOI: 10.1039/c5sc03021h
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Open Access (Creative Commons)
Description:

Correction: Unique post-translational oxime formation in the biosynthesis of the azolemycin complex of novel ribosomal peptides from Streptomyces sp. FXJ1.264
Ning Liu, Lijiang Song, Minghao Liu, Fei Shang, Zoe Anderson, David J. Fox, Gregory L. Challis, Ying Huang
Chem Sci. 2016 Jan 1; 7(1): 810. Published online 2015 Nov 5. doi: 10.1039/c5sc90063h

Date of first compliant deposit: 18 August 2016
Date of first compliant Open Access: 18 August 2016
Funder: NSFC, Biotechnology and Biological Sciences Research Council (Great Britain) (BBSRC)
Grant number: 31170010 (NSFC), 31300010 (NSFC), BB/L010852/1 (BBSRC)

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