Biosynthetic preparation of labeled cerulenin with high specific radioactivity.

The Journal of Antibiotics
1987.0

Abstract

Cerulenin, (2R)(3S)-2,3-epoxy-4-oxo-E,E'-7,10 dodecadienoylamide, is a potent inhibitor of fatty acid synthase systems isolated from various microorganisms and animal tissues.1} This antibiotic specifically blocks the activity of 2-oxoacyl thioester synthase (condensing enzyme).1} We have proposed that cerulenin covalently binds to the cysteine-SH at the active center of the condensing enzyme.2,3) Cerulenin has also been found to inhibit the biosynthesis of various polyketide-derived secondary metabolites such as macrolides4) and nanaomycin.5) Because of its unique mode of action and usefulness as a biological reagent, attempts were made to prepare [3H]- and [14C]cerulenin by the present authors6,7) and other research groups.8) Labeled cerulenin has been used for the binding and active-site studies on fatty acid synthase.6-8) However, the specific radioactivities of these preparations were not very high (0.46 and 0.016 mCi/mmol of [3H]cerulenin)7) although Tsukamoto et al.8) reported on [14C]cerulenin with fairly high specific radioactivity (2.21 mCi/mmol). On the other hand, Robert and Leadlay9,10) prepared [3H]tetrahydrocerulenin (45 Ci/mmol) by chemical reduction of cerulenin with tritium gas over PtO2. The purpose of this paper is to present a method of biosynthetic preparation of labeled cerulenin with high specific radioactivity. This method yielded 13.2 mCi/mmol of [3H]cerulenin.

Knowledge Graph

Similar Paper

Biosynthetic preparation of labeled cerulenin with high specific radioactivity.
The Journal of Antibiotics 1987.0
Structure−Activity Studies of Cerulenin Analogues as Protein Palmitoylation Inhibitors
Journal of Medicinal Chemistry 1999.0
Bioconversion and biosynthesis of nanaomycins using cerulenin, a specific inhibitor of fatty acid and polyketide biosyntheses.
The Journal of Antibiotics 1980.0
Biosynthetic preparation of radioactively labeled erbstatin.
The Journal of Antibiotics 1992.0
New ansamycin antibiotics, naphthoquinomycins A and B, inhibitors of fatty acid synthesis in Escherichia coli.
The Journal of Antibiotics 1986.0
The biosynthesis of caerulomycins in <i>Streptomyces</i> <i>caeruleus</i>. Isolation of a new caerulomycin and incorporation of picolinic acid and glycerol into caerulomycin A
Canadian Journal of Chemistry 1988.0
Further Studies on the Biosynthesis of Granaticin
Zeitschrift für Naturforschung C 1986.0
Studies on the biosynthesis of thiostrepton: 4-(1-hydroxyethyl)quinoline-2-carboxylate as a free intermediate on the pathway to the quinaldic acid moiety
Bioorganic &amp; Medicinal Chemistry 1996.0
Synthetic Secofriedelane and Friedelane Derivatives as Inhibitors of Human Lymphocyte Proliferation and Growth of Human Cancer Cell Lines in Vitro
Journal of Natural Products 2001.0
Studies on the Synthesis of Sesquiterpene Lactones, 12. Synthesis of (+)-Colartin, (+)-Arbusculin A and Their C-4 Epimers and Their Biological Activities
Journal of Natural Products 1991.0