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

• Published in: Organic & biomolecular chemistry Vol. 14; no. 26; pp. 6289 - 6296
• Main Authors: Bhadra, Pranab K., Hassanzadeh, Abdolreza, Arsic, Biljana, Allison, David G., Morris, Gareth A., Barber, Jill
• Format: Journal Article
• Language: English
• Published: England 01.01.2016
• Subjects: Alcohols - chemical synthesis; Alcohols - chemistry; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Catalysis; Erythromycin - analogs & derivatives; Erythromycin - chemical synthesis; Erythromycin - chemistry; Erythromycin - pharmacology; Ethers - chemical synthesis; Ethers - chemistry; Gram-Negative Bacteria - drug effects; Gram-Negative Bacteria - growth & development; Gram-Positive Bacteria - drug effects; Gram-Positive Bacteria - growth & development; Hydrogen-Ion Concentration; Microbial Sensitivity Tests; Molecular Conformation; Oxidation-Reduction

Erythromycin B is structurally very similar to erythromycin A, and also shares its clinically important antibacterial activity. Its potential advantage is that it is much more stable to acid. Both compounds are susceptible to 6–9-enol ether formation, involving loss of a proton from C-8. The enol et...