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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 .