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Synthesis of the C1-C27 fragment of stambomycin D validates modular polyketide synthase-based stereochemical assignments

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Lim, Jieyan, Chintalapudi, Venkaiah, Gudmundsson, Haraldur G, Tran, Minh, Bernasconi, Alice, Blanco, Araceli, Song, Lijiang, Challis, Gregory L. and Anderson, Edward A (2021) Synthesis of the C1-C27 fragment of stambomycin D validates modular polyketide synthase-based stereochemical assignments. Organic Letters, 23 (19). pp. 7439-7444. doi:10.1021/acs.orglett.1c02650 ISSN 1523-7060.

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Official URL: https://doi.org/10.1021/acs.orglett.1c02650

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Abstract

The stambomycins are a family of bioactive macrolides isolated from <i>Streptomyces ambofaciens</i>. Aside from two stereocenters installed through cytochrome P450 oxidations, their stereochemistry has been predicted by sequence analysis of the polyketide synthase. We report a synthesis of the C1-C27 fragment of stambomycin D, the spectroscopic data of which correlates well with that of the natural product, further validating predictive sequence analysis as a powerful tool for stereochemical assignment of complex polyketide natural products.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
SWORD Depositor: Library Publications Router
Library of Congress Subject Headings (LCSH): Stereochemistry, Alcohols, Chemistry, Organic -- Research, Ring formation (Chemistry)
Journal or Publication Title: Organic Letters
Publisher: American Chemical Society
ISSN: 1523-7060
Official Date: 1 October 2021
Dates:
DateEvent
1 October 2021Published
8 September 2021Available
8 September 2021Accepted
Volume: 23
Number: 19
Page Range: pp. 7439-7444
DOI: 10.1021/acs.orglett.1c02650
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Open Access (Creative Commons)
Date of first compliant deposit: 29 October 2021
Date of first compliant Open Access: 2 November 2021
RIOXX Funder/Project Grant:
Project/Grant IDRIOXX Funder NameFunder ID
RPG-2015-003Leverhulme Trusthttp://dx.doi.org/10.13039/501100000275
EP/S013172/1[EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
702385H2020 Marie Skłodowska-Curie ActionsUNSPECIFIED
Related URLs:
  • https://doi.org/10.1021/acs.orglett.1c02...
  • https://europepmc.org/articles/PMC849115...
  • https://europepmc.org/articles/PMC849115...

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