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Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst.

ABSTRACT: Thiopeptides are a class of potent antibiotics with promising therapeutic potential. We developed a novel Mo(vi)-oxide/picolinic acid catalyst for the cyclodehydration of cysteine peptides to form thiazoline heterocycles. With this powerful tool in hand, we completed the total syntheses of two representative thiopeptide antibiotics: micrococcin P1 and thiocillin I. These two concise syntheses (15 steps, longest linear sequence) feature a C-H activation strategy to install the trisubstituted pyridine core and thiazole groups. The synthetic material displays promising antimicrobial properties measured against a series of Gram-positive bacteria.

SUBMITTER: Akasapu S

PROVIDER: S-EPMC6383332 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst.

Akasapu Siddhartha S Hinds Aaron B AB Powell Wyatt C WC Walczak Maciej A MA

Chemical science 20181203 7

Thiopeptides are a class of potent antibiotics with promising therapeutic potential. We developed a novel Mo(vi)-oxide/picolinic acid catalyst for the cyclodehydration of cysteine peptides to form thiazoline heterocycles. With this powerful tool in hand, we completed the total syntheses of two representative thiopeptide antibiotics: micrococcin P1 and thiocillin I. These two concise syntheses (15 steps, longest linear sequence) feature a C-H activation strategy to install the trisubstituted pyri ...[more]

PMID: 30881626

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