Translactonization of erythromycin A during oximation: mixture analysis and reaction monitoring by NMR | Zendy

Grover Rajesh K. | Zendy; Joshi B. S. | Zendy; Batra S. | Zendy; Roy Raja | Zendy; Bhaduri A. P. | Zendy

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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.

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