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

ABSTRACT: 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.

SUBMITTER: Lim J

PROVIDER: S-EPMC8491158 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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

Lim Jieyan J Chintalapudi Venkaiah V Gudmundsson Haraldur G HG Tran Minh M Bernasconi Alice A Blanco Araceli A Song Lijiang L Challis Gregory L GL Anderson Edward A EA

Organic letters 20210908 19

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 ass ...[more]

PMID: 34494848

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