Comparison of fatty acid and polyketide biosynthesis: stereochemistry of cladosporin and oleic acid formation in Cladosporium cladosporioides

BJ Rawlings, PB Reese, SE Ramer…

Index: Rawlings, Bernard J.; Reese, Paul B.; Ramer, Shawn E.; Vederas, John C. Journal of the American Chemical Society, 1989 , vol. 111, # 9 p. 3382 - 3390

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Citation Number: 48

Abstract

Abstract: Stereochemical aspects of the biosynthesis of the polyketide cladosporin (1) and of oleic acid (2) by Cladosporium cladosporioides NRRL 5507 were compared by use of stable isotope labeling and 2D NMR spectrometry. The absolute stereochemistry of 1 was confirmed by degradation to (2R, 6S)-(-)-(6-methyltetrahydropyran-2-yl) acetic acid (12). Incorporations of sodium [I-l3C]-,[2-I3C]-,[1, 2-I3C2]-,[l-'3C,'802]-,[1-'3C, 2H3]-, and [2-13C, ...