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. 2006 Jan;71(1):34-41.
doi: 10.1016/j.steroids.2005.08.003. Epub 2005 Sep 23.

Aerial oxidation of the glucocorticoid side-chain under pH control

John S Edmonds  1 , Masatoshi Morita, Peter Turner, Brian W Skelton, Allan H White
Affiliations

Aerial oxidation of the glucocorticoid side-chain under pH control

John S Edmonds et al. Steroids. 2006 Jan.

Abstract

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.

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