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Author Maehr, H. ♦ Leach, M. ♦ Yarmchuk, L. ♦ Mitrovic, M.
Source J-STAGE
Content type Text
Publisher JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
Language English
Abstract Mocimycin was converted to the acylesters by selective acylation of the hydroxyl group of the 4-hydroxy-1-methyl-2(1H)pyridinone moiety. Subsequent N-methylation at the nuclear nitrogen and removal of the protective group from the resulting reaction products afforded aurodox. Mono-O-acetylmocimycin and several analogous aurodox esters thus prepared possess antibacterial activity in vitro and growth-promotion properties in poultry. Esters of aurodox involving the hydroxyl group of the 4-hydroxy-1-methyl-2(1H)pyridinone moiety are activated. Accordingly, acetic acid treatment of the aurodox esters generates O-acylgoldinamines which undergo transacylation furnishing N-acylgoldinamines. Alternatively, N-acylgoldinamines can be prepared by selective mono-O-arylsulfonylation of aurodox, liberating O-arylsulfonylgoldinamine by treatment with acetic acid followed by N-acylation and removal of the protective arylsulfonyl group. A third approach to N-acylgoldinamines consists in direct N-acylation of goldinamine itself which is prepared by acetic acid treatment of aurodox. None of these derivatives prepared, however, exhibited significant antimicrobial or growth-promoting properties, suggesting that the goldinonic acid moiety, or a closely related derivative thereof, is required for biological activity.
ISSN 00218820
Learning Resource Type Article
Publisher Date 1979-01-01
e-ISSN 18811469
Journal The Journal of Antibiotics(antibiotics1968)
Volume Number 32
Issue Number 4
Page Count 7
Starting Page 361
Ending Page 367


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