Antimetabolites produced by microorganisms. XIII. The synthesis and microbiological production of a novel amino acid, L-2-amino-4-(2-aminoethoxy) butanoic acid.

A novel amino acid, L-2-amino-4-(2-aminoethoxy)-butanoic acid, was isolated from a fermentation broth of Streptomyces sp. X-11, 085. It was shown to be identical with the chemical reduction product of an antimetabolite antibiotic, L-2-amino-4-(2-aminoethoxy)-trans-3-butenoic acid, a co-product in the fermentation. Addition of the title compound to the fermentation led to an enhanced yield of the antimetabolitesuggesting that the saturated amino acid serves as a precursor for the antimetabolite.A de novo chemical synthesis and enzymatic resolution of the title compound are also reported.