PMID: 11902879Mar 21, 2002Paper

Nonactin biosynthesis: the initial committed step is the condensation of acetate (malonate) and succinate

Journal of the American Chemical Society
Michael E Nelson, Nigel D Priestley

Abstract

Nonactin is a macrotetrolide antibiotic produced by Streptomyces griseus subsp. griseus ETH A7796 that has shown activity against the P170-glycoprotein efflux pump associated with multiple drug resistant cancer cells. Nonactin is a polyketide, albeit a highly atypical one. The structure is composed of two units of each of the enantiomers of nonactic acid, arranged in a macrocycle, so that the molecule has S4 symmetry and is achiral. The monomer units, (+)- and (-)-nonactic acid, are derived from acetate, succinate, and propionate, although the exact details of the assembly process are quite unclear. We have used feeding experiments with a series of multiple stable isotope labeled precursors to elucidate the details of the first committed step of nonactic acid biosynthesis. We have found that the (13)C label from 3-ketoadipate is incorporated specifically into both nonactic acid and its homologue, homononactic acid. The data conclusively show that the first committed step of nonactin biosynthesis is the coupling of a succinate derivative with either acetate or malonate. The differentiation into either nonactate or homononactate occurs after the initial condensation; the homologues are not derived from use of a different "starter...Continue Reading

References

Jan 1, 1972·Helvetica Chimica Acta·M Dobler

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Citations

Apr 12, 2011·The Journal of Chemical Physics·Christie AroulandaPhilippe Lesot
Apr 26, 2016·Accounts of Chemical Research·Herbert Mayr, Armin R Ofial
Jul 14, 2016·Canadian Journal of Microbiology·Yulian Zhan, Shaolun Zheng
May 5, 2012·Angewandte Chemie·Jennifer M FinefieldRobert M Williams
Aug 26, 2016·Beilstein Journal of Organic Chemistry·Franziska Hemmerling, Frank Hahn
Dec 7, 2002·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Ben Shen, Hyung-Jin Kwon
Aug 2, 2003·Critical Reviews in Biotechnology·Christopher D Reeves
Nov 16, 2010·Angewandte Chemie·Alex M Szpilman, Erick M Carreira
Dec 30, 2014·Angewandte Chemie·Yuriy RebetsAndriy Luzhetskyy
Jun 25, 2021·The Journal of Antibiotics·Changxiang ShiJoong Sup Shim
Aug 24, 2002·Science·Hyung-Jin KwonBen Shen

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