Enhancement of the properties of a drug by mono-deuteriation: reduction of acid-catalysed formation of a gut-motilide enol ether from 8-deuterio-erythromycin B

Author:

Bhadra Pranab K.1234,Hassanzadeh Abdolreza1234,Arsic Biljana1234,Allison David G.1234,Morris Gareth A.5234,Barber Jill1234

Affiliation:

1. Manchester Pharmacy School

2. University of Manchester

3. Manchester

4. UK

5. School of Chemistry

Abstract

An efficient synthesis of 8-d-erythromycin B was achieved. A deuterium isotope effect suppresses formation of the corresponding enol ether, which may result in reduced gut-motilide effects.

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Reference40 articles.

1. G. Katzung Bertram , Basic & clinical pharmacology, McGraw-Hill, New York, 8th edn, 2001, p. 64

2. A. D. Buss and R. D.Waigh, in Burger's medicinal chemistry and drug discovery, ed. M. E. Wolff, John Wiley & Sons, New York, 5th edn, 1995, vol. 1, pp. 1009–1012

3. Anhydrolide Macrolides. 2. Synthesis and Antibacterial Activity of 2,3-Anhydro-6-O-methyl 11,12-Carbazate Erythromycin A Analogues

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