Aerial oxidation of the glucocorticoid side-chain under pH control

J.S. Edmonds, M. Morita, P. Turner, Brian Skelton, Allan White

Research output: Contribution to journalArticlepeer-review

10 Citations (Web of Science)


The outcome of aerial oxidation of the glucocortico-steroid side-chain (as exemplified by dexamethasone) has been shown to be subject to strict pH control. At pH 7.4 the glyoxal is the only product; at pH values of 8 and 9.2 the etioacid is formed, and at pH values of 13 or above the epimeric glycolic acids are produced. The glycolic acid epimer that predominates by a factor of 2 and is more stable has been shown by an X-ray crystal structural analysis to be the 20R. compound. The presence of arsenite changes the course of the reaction and only the glycolic acids are yielded at pH values of 8 and above. (c) 2005 Elsevier Inc. All rights reserved.
Original languageEnglish
Pages (from-to)34-41
Issue number1
Publication statusPublished - 2006


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