✦ LIBER ✦

The so-called “interconversion” of stereoisomeric drugs: An attempt at clarification

✍ Scribed by Dr. Bernard Testa; Pierre-Alain Carrupt; Joseph Gal

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 619 KB
Volume: 5
Category: Article
ISSN: 0899-0042
DOI: 10.1002/chir.530050302

No coin nor oath required. For personal study only.

✦ Synopsis

A variety of reactions can be categorized under the global concept of the "interconversion of stereoisomers. " Thus, racemization or epimerization can result from inversion of labile chiral centers. From the examples available, some predictive rules are suggested for a chiral center of the type R"R'RC-H undergoing base-catalyzed inversion and a provisional table of affecting groups is presented. Unimolecular inversion of nonsymmetrical, nonplanar ring systems can also result in racemization or epimerization, but no generalization can yet be offered. Beside these cases of nonenzymatic reactions, a limited variety of enzymatic reactions can operate to interconvert stereoisomers, the outcome rarely being a racemic mixture. An important aspect of stereoisomer interconversion is the time scale in which the phenomenon is observed. Thus, several reactions to nonezymatic racemization or epimerization are fast compared to the duration of action of the drug and therefore have pharmacological sigmficance, while other are slower and are of pharmaceutical relevance only.

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