Metabolic products of microorganisms. 228. New nikkomycins produced by mutants of Streptomyces tendae.

Abstract

Four new dipeptidyl nikkomycins of the Z- and the X-series with a variation in the amino acid moiety of the molecule were isolated from the mutant S. tendae 901/395 and characterized. Nikkomycins Kz and Kx contain 2-amino-4-hydroxy-4-(2-pyridyl)butyric acid, and nikkomycins Oz and Ox 2-amino-4-hydroxy-4-(5-hydroxy-2-pyridyl)butyric acid. In contrast to nikkomycins Z and X, nikkomycins Kz and Ox are quite stable at alkaline pH, and exhibit a lower biological activity against various test organisms. From the mutant S. tendae 901/C37, which is auxotrophic for methionine and threonine, enhanced amounts of 2 tripeptidyl nikkomycins, Qz and Qx, were produced which are analogs of nikkomycins J and I, and contain a homoserine residue instead of glutamic acid. These nikkomycins exhibit a high pH instability.