Synthesis of the C1–C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments

[Image: see text] The stambomycins are a family of bioactive macrolides isolated from Streptomyces ambofaciens. 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 o...

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Autores principales: Lim, Jieyan, Chintalapudi, Venkaiah, Gudmundsson, Haraldur G., Tran, Minh, Bernasconi, Alice, Blanco, Araceli, Song, Lijiang, Challis, Gregory L., Anderson, Edward A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8491158/
https://www.ncbi.nlm.nih.gov/pubmed/34494848
http://dx.doi.org/10.1021/acs.orglett.1c02650
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author Lim, Jieyan
Chintalapudi, Venkaiah
Gudmundsson, Haraldur G.
Tran, Minh
Bernasconi, Alice
Blanco, Araceli
Song, Lijiang
Challis, Gregory L.
Anderson, Edward A.
author_facet Lim, Jieyan
Chintalapudi, Venkaiah
Gudmundsson, Haraldur G.
Tran, Minh
Bernasconi, Alice
Blanco, Araceli
Song, Lijiang
Challis, Gregory L.
Anderson, Edward A.
author_sort Lim, Jieyan
collection PubMed
description [Image: see text] The stambomycins are a family of bioactive macrolides isolated from Streptomyces ambofaciens. 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.
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spelling pubmed-84911582021-10-05 Synthesis of the C1–C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments Lim, Jieyan Chintalapudi, Venkaiah Gudmundsson, Haraldur G. Tran, Minh Bernasconi, Alice Blanco, Araceli Song, Lijiang Challis, Gregory L. Anderson, Edward A. Org Lett [Image: see text] The stambomycins are a family of bioactive macrolides isolated from Streptomyces ambofaciens. 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. American Chemical Society 2021-09-08 2021-10-01 /pmc/articles/PMC8491158/ /pubmed/34494848 http://dx.doi.org/10.1021/acs.orglett.1c02650 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Lim, Jieyan
Chintalapudi, Venkaiah
Gudmundsson, Haraldur G.
Tran, Minh
Bernasconi, Alice
Blanco, Araceli
Song, Lijiang
Challis, Gregory L.
Anderson, Edward A.
Synthesis of the C1–C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments
title Synthesis of the C1–C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments
title_full Synthesis of the C1–C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments
title_fullStr Synthesis of the C1–C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments
title_full_unstemmed Synthesis of the C1–C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments
title_short Synthesis of the C1–C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments
title_sort synthesis of the c1–c27 fragment of stambomycin d validates modular polyketide synthase-based stereochemical assignments
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8491158/
https://www.ncbi.nlm.nih.gov/pubmed/34494848
http://dx.doi.org/10.1021/acs.orglett.1c02650
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