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Pentamycin biosynthesis in Philippine Streptomyces sp. S816 : cytochrome P450-catalyzed installation of the C-14 hydroxyl group
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Zhou, Shanshan, Song, Lijiang, Masschelein, Joleen, Sumang, Felaine A. M., Papa, Irene A., Zulaybar, Teofila O., Custodio, Aileen B., Zabala, Daniel, Alcantara, Edwin P., Emmanuel de los Santos, L. C. and Challis, Gregory L. (2019) Pentamycin biosynthesis in Philippine Streptomyces sp. S816 : cytochrome P450-catalyzed installation of the C-14 hydroxyl group. ACS Chemical Biology, 14 (6). pp. 1305-1309. doi:10.1021/acschembio.9b00270 ISSN 1554-8929.
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WRAP-pentamycin-biosynthesis-Philippine-Streptomyces-sp.S816-Challis-2019.pdf - Accepted Version - Requires a PDF viewer. Download (647Kb) | Preview |
Official URL: http://dx.doi.org/10.1021/acschembio.9b00270
Abstract
Pentamycin is a polyene antibiotic, registered in Switzerland for the treatment of vaginal candidiasis, trichomoniasis, and mixed infections. Chemical instability has hindered its widespread application and development as a drug. Here, we report the identification of Streptomyces sp. S816, isolated from Philippine mangrove soil, as a pentamycin producer. Genome sequence analysis identified the putative pentamycin biosynthetic gene cluster, which shows a high degree of similarity to the gene cluster responsible for filipin III biosynthesis. The ptnJ gene, which is absent from the filipin III biosynthetic gene cluster, was shown to encode a cytochrome P450 capable of converting filipin III to pentamycin. This confirms that the cluster directs pentamycin biosynthesis, paving the way for biosynthetic engineering approaches to the production of pentamycin analogues. Several other Streptomyces genomes were found to contain ptnJ orthologues clustered with genes encoding polyketide synthases that appear to have similar architectures to those responsible for the assembly of filipin III and pentamycin, suggesting pentamycin production may be common in Streptomyces species.
| Item Type: | Journal Article | ||||||||||||||||||
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| Subjects: | R Medicine > RM Therapeutics. Pharmacology | ||||||||||||||||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||||||||||||
| Library of Congress Subject Headings (LCSH): | Polyene antibiotics, Streptomyces, Biochemistry | ||||||||||||||||||
| Journal or Publication Title: | ACS Chemical Biology | ||||||||||||||||||
| Publisher: | American Chemical Society | ||||||||||||||||||
| ISSN: | 1554-8929 | ||||||||||||||||||
| Official Date: | 21 June 2019 | ||||||||||||||||||
| Dates: |
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| Volume: | 14 | ||||||||||||||||||
| Number: | 6 | ||||||||||||||||||
| Page Range: | pp. 1305-1309 | ||||||||||||||||||
| DOI: | 10.1021/acschembio.9b00270 | ||||||||||||||||||
| Status: | Peer Reviewed | ||||||||||||||||||
| Publication Status: | Published | ||||||||||||||||||
| Reuse Statement (publisher, data, author rights): | This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Chemical Biology, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acschembio.9b00270 | ||||||||||||||||||
| Access rights to Published version: | Restricted or Subscription Access | ||||||||||||||||||
| Date of first compliant deposit: | 17 June 2019 | ||||||||||||||||||
| Date of first compliant Open Access: | 16 May 2020 | ||||||||||||||||||
| RIOXX Funder/Project Grant: |
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