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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
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Official URL: http://dx.doi.org/10.1039/C5SC03021H
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 | ||||||||
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| Subjects: | Q Science > QD Chemistry Q Science > QP Physiology |
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| Divisions: | Faculty of 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: |
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| Date of first compliant deposit: | 18 August 2016 | ||||||||
| 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 | ||||||||
| Description: | Correction: 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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| 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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