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Translactonization of erythromycin A during oximation: mixture analysis and reaction monitoring by NMR
Author(s) -
Grover Rajesh K.,
Joshi B. S.,
Batra S.,
Roy Raja,
Bhaduri A. P.
Publication year - 2001
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.858
Subject(s) - chemistry , erythromycin , enol ether , methanol , oxime , hydrazine (antidepressant) , enol , ether , proton nmr , hydrochloride , hydroxylamine , organic chemistry , nuclear magnetic resonance spectroscopy , stereochemistry , medicinal chemistry , chromatography , catalysis , antibiotics , biochemistry
Oximation of erythromycin A with hydroxylamine hydrochloride and sodium acetate in methanol led to the formation of pseudoerythromycin A enol ether with erythromycin A oxime as analysed by detailed two‐dimensional NMR spectroscopy in the mixture along with traces of 8,9‐anhydroerythromycin A 6,9‐hemiketal and erythromycin A 6,9:9,12‐spiroketal. The formation of the degraded products was established by performing in situ 13 C NMR spectroscopy. The analysis suggests that pseudoerythromycin A enol ether is formed by the translactonization of erythromycin A enol ether which forms as a result of acid degradation. Copyright © 2001 John Wiley & Sons, Ltd.