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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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WRAP-Synthesis-C1−C27-fragment-stambomycin-D-validates-modular-polyketide-synthase-stereochemical-2021.pdf - Published Version - Requires a PDF viewer. Available under License Creative Commons Attribution 4.0. Download (1898Kb) | Preview |
Official URL: https://doi.org/10.1021/acs.orglett.1c02650
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 | ||||||||||||
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| 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: |
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| 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: |
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