title: An unusual intramoleculartrans-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 intramoleculartrans-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.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, United States.
authors.forename: Heriberto
authors.initials: H
authors.lastname: Rivera
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, United States.
authors.forename: Sachin
authors.initials: S
authors.lastname: Dhar
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, United States.
authors.forename: James J
authors.initials: JJ
authors.lastname: La Clair
authors.affiliation: Departments of Molecular Biology and Biochemistry, Chemistry, and Pharmaceutical Sciences, University of California, Irvine, California 92697, United States.
authors.forename: Shiou-Chuan
authors.initials: SC
authors.lastname: Tsai
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, United States.
authors.forename: Michael D
authors.initials: MD
authors.lastname: Burkart
keywords: Cyclization; Intramolecular reactions; Polyketide; Reaction mechanisms; Trans-amidation