Process for the preparation of new aminocyclitol antibiotics

• Main Authors: ROBERT LAGRONE CLARKE, SOL JACOB DAUM
• Format: Patent
• Language: English
• Published: 30.06.1980
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; APPARATUS THEREFOR; BEER; BIOCHEMISTRY; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; DERIVATIVES THEREOF; ENZYMOLOGY; FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE; GENERAL METHODS OF ORGANIC CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; MICROBIOLOGY; MUTATION OR GENETIC ENGINEERING; NUCLEIC ACIDS; NUCLEOSIDES; NUCLEOTIDES; ORGANIC CHEMISTRY; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; SPIRITS; SUGARS; THEIR RELEVANT APPARATUS; TRANSPORTING; VINEGAR; WINE

New analogues of gentamicin C1, C2 and C1a as well as compounds thereof which are acylated on the 1-amino, 3-amino and 2'-amino groups by a lower omega -amino- alpha -hydroxyalkanoyl group are prepared. For this, a nutrient medium is produced containing carbohydrates, a source of assimilable nitrogen, essential salts and an aminocyclitol added in the presence of a mutant microorganism which is incapable of synthesising the said aminocyclitol itself but which is capable of incorporating the said aminocyclitol into the said new aminocyclitol, and if desired, the product obtained is acylated with an ester of a lower omega -(N-benzyloxycarbonyl)amino- alpha -hydroxyalkanoic acid and then the benzyloxycarbonyl group is removed by catalytic hydrogenolysis. The new compounds possess an antibacterial activity, in particular towards gentamicin-resistant microorganisms; they are useful as antibacterial agents.