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An unusual intramolecular trans-amidation.

ABSTRACT: Polyketide biosynthesis engages a series of well-timed biosynthetic operations to generate elaborate natural products from simple building blocks. Mimicry of these processes has offered practical means for total synthesis and provided a foundation for reaction discovery. We now report an unusual intramolecular trans-amidation reaction discovered while preparing stabilized probes for the study of actinorhodin biosynthesis. This rapid cyclization event offers insight into the natural cyclization process inherent to the biosynthesis of type II polyketide antibiotics.

SUBMITTER: Rivera H

PROVIDER: S-EPMC4917018 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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An unusual intramolecular <i>trans</i>-amidation.

Rivera Heriberto H Dhar Sachin S La Clair James J JJ Tsai Shiou-Chuan SC Burkart Michael D MD

Tetrahedron 20160601 25

Polyketide biosynthesis engages a series of well-timed biosynthetic operations to generate elaborate natural products from simple building blocks. Mimicry of these processes has offered practical means for total synthesis and provided a foundation for reaction discovery. We now report an unusual intramolecular <i>trans</i>-amidation reaction discovered while preparing stabilized probes for the study of actinorhodin biosynthesis. This rapid cyclization event offers insight into the natural cycliz ...[more]

PMID: 27346894

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