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Incorporation of L-[2- 2 H]phenyl-[2- 2 H]alanine and L-phenyl-[2- 13 C,  15 N]alanine into cytochalasin D by Zygosporium masonii involved the complete loss of both the α- 2 H- and the α- 15 N-atom. Incorporation of a mixture of L-phenyl-[ 15 N]alanine and L-[U- 14 C]phenylalanine into cytochalasin D and protein amino acids (phenylalanine, leucine, isoleucine) was accompanied by a substantial loss of  15 N with respect to  14 C. These effects are attributed to rapid exchange reactions taking place while L-phenylalanine is part of the intracellular pool of amino acids. In addition, the medium- and concentration-dependent incorporation of the carbon skeleton of exogeneous D-phenylalanine into cytochalasin D is reported. In a peptone-based complex medium, D-phenylalanine is poorly incorporated. Throughout the whole concentration range (0-250 mg/l), the incorporation rates are less than 10% of those of L-phenylalanine. In a minimal medium containing NH 4 NO 3  as nitrogen source however, D-phenylalanine is preferred over the natural enantiomer by a factor of 1.28 up to 6.78, depending on the concentrations of exogeneous D - and L-phenylalanine. These effects are attributed to the medium-dependent activities of different amino acid transport systems responsible for the uptake of D - and L-phenylalanine in Z. masonii.

Biosynthesis of Cytochalasans. XI. New Results on the Incorporation of Phenylalanine into Cytochalasin D by Zygosporium masonii [1]