Study on Orientomycin, Identified With D-4-Amino-3-Isoxazolidone Studies on Actinomyces Antibiotics. XXXVII

Abstract

Orientomycin^(1,2) is an antibiotic produced by a strain of streptomyces (K-300),^(3,4) upon which several reports have been published already. In those papers the antibiotic was called Special Substance No. 2^(3,5) or K-300 substance^(6,7). At that time, we could not obtain it in a pure form, although we were interested in its characteristic properties.

In those previous papers, it was reported that the antibiotic was soluble in water but insoluble in almost all organic solvents, scarcely adsorbed on carbon and alumina, and it showed an amphoteric behavior on electrophoretic papergram. It was also described that the antibiotic gave ninhydrin reaction in yellowish tinge, and among the degradation products of the antibiotic a substance migrated as glutamic acid or serine on the paperchromatography. Furthermore, it was recognized that the antibiotic inhibited gram positive bacteria, gram negative bacteria and tubercle bacilli in vitro, and its toxicity for mice was very low.

Thereafter, several laboratories reported the isolation of new antibiotics (oxamycin^(8,9,10) , cycloserinem^(11,12) , and PA-94⁽¹³⁾) which were identical with each other, and the structure of these antibiotics was determined as D-4-amino-3-isoxazolidone. The resemblance between characteristic properties of our orientomycin and that of D-4-amino-3-isoxazolidone came into our notice. Therefore, we carried out the purification of orientomycin according to the almost similar procedure as that used in oxamycin. Consequently, orientomycin was prepared in a pure form and identified as D-4-amino-3-isoxazolidone. The present paper deals with the purification, physico-chemical and biological properties and the identification of orientomycin.