The Chemistry of Pyridomycin

Abstract

Structural studies on pyridomycin have been performed by chemical degradation such as ozonolysis and hydrolysis in alkaline and acidic media. New acids, α-oxo-β-methylvaleric acid, 4-amino-3-hydroxy-2-methyl-5-(3-pyridyl)pentanoic acid and its dehydration and deamination products are obtained as degradation products. The structure I, 10-hydroxy-6-(3-hydroxypicolinamido)-5, 11-dimethyl-2-(1-methylpropylidene)-9-(3-pyridylmethyl)-8-aza-1,4-dioxa-cyclododecane-3,7,12-trione, has been proposed for pyridomycin. This structure including its stereochemistry was recently determined by X-ray analysis of the crystal of pyridomycin dihydrobromide (C27H32O8N4⋅2HBrβH2O⋅CH3CH2OCOCH3).2). © 1968, The Pharmaceutical Society of Japan. All rights reserved.