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Biosynthesis of Cytochalasans. Part 6. The Mode of Incorporation of Phenylalanine into Cytochalasin D

✍ Scribed by John C. Vederas; Christoph Tamm

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
598 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Rapid equilibrium of D‐ and L‐phenylalanines with phenylpyruvic acid (4) was shown to account for their equally efficient incorporation into cytochalasin D (1) by Zygosporium masonii. Transamination of phenylalanines stereospecifically labelled with tritium at C(2) and C(3) proceeded with complete hydrogen loss at the Ξ± position and extensive loss at the Ξ² position. Considerable suppression of the incorporation of the D‐amino acid by phenylpyruvic acid (4) indicated that the L‐enantiomer is the primary precursor of 1.

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