ABSTRACT
The purification of a new antibiotic, Ro 22-5417, was achieved by a variety of preparative column chromatographic methods. The antibiotic was obtained crystalline with an overall recovery of 3% after a 300-fold purification. The structure was determined from proton and 13C NMR spectra to be 3-(7-oxo-1-aza-4-oxabicyclo[3.2.0]hept-3-yl)alanine.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Clavulanic Acids/isolation & purification , Streptomyces/metabolism , Chemical Phenomena , Chemistry , Chromatography/methods , Fermentation , Magnetic Resonance Spectroscopy , Spectrophotometry, InfraredABSTRACT
A new antibiotic, 3-O-oleandrosyl-5-O-desosaminylerythronolide A oxime (3) was produced from erythronolide A oxime (1) by the oleandomycin-producing culture, Streptomyces antibioticus ATCC 11891. The structure of 3 was determined by degradative studies and confirmed by X-ray analysis. Compound 3 was found to be less active, but more stable to acid, then erythromycin A oxime.
Subject(s)
Anti-Bacterial Agents , Erythromycin/analogs & derivatives , Oleandomycin/analogs & derivatives , Anti-Bacterial Agents/analysis , Anti-Bacterial Agents/biosynthesis , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Drug Stability , Erythromycin/pharmacology , Fermentation , Iodides , Models, Chemical , Oleandomycin/pharmacology , Oximes , Streptomyces antibioticus/metabolism , X-Ray DiffractionABSTRACT
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 antimetabolite suggesting that the saturated amino acid serves as a precursor for the antimetabolite.
Subject(s)
Aminobutyrates , Aminobutyrates/chemical synthesis , Aminobutyrates/isolation & purification , Aminobutyrates/pharmacology , Bacteria/drug effects , Catalysis , Fermentation , Oxidation-Reduction , Streptomyces/metabolismABSTRACT
(S)-Alanyl-3-[alpha-(S)-chloro-3-(S)-hydroxy-2-oxo-3-azetidinylmethyl]-(S)-alanine was isolated from a fermentation broth of an unidentified Streptomyces species 372 A. The structure was determined by single crystal X-ray diffraction analysis. The substance inhibits the growth of several strains of gram-positive and gram-negative bacteria in a chemically defined medium but growth inhibition is relieved by addition of L-glutamine to the medium.
