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

Vederas John C. | Zendy; Tamm Christoph | Zendy

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

Author(s) -

Vederas John C.,

Tamm Christoph

Publication year - 1976

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19760590221

Subject(s) - chemistry , phenylpyruvic acid , transamination , phenylalanine , enantiomer , stereochemistry , tritium , biochemistry , amino acid , physics , nuclear physics

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 α position and extensive loss at the β 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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