Stereochemistry and Biological Activity of Methyl Hydrogen 3-Phenyl-2,2′-iminodipro-pionate Produced by Botrytis squamosa

Abstract

The stereochemistry of 1-methyl hydrogen 3-phenyl-2,2′-iminodipropionate (BSF-A, 1) was determined to be 2S, 2′S by comparing the spectral data of 1 with those of synthetic derivatives. The effects of BSF-A (1) and its analogs on the growth rate of lettuce seedlings were examined. Both diastereomers, 3a (2S,2′S) and 3b (2S, 2′R), of dimethyl 3-phenyl-2,2′-iminodipropionate and a regioisomer, 1’-methyl hydrogen 3-phenyl-2,2′-iminodipropionate (2), exhibited biological activity similar to that of natural product BSF-A (1).