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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Aerial oxidation of the glucocorticoid side-chain under pH control.

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.[1]

References

  1. Aerial oxidation of the glucocorticoid side-chain under pH control. Edmonds, J.S., Morita, M., Turner, P., Skelton, B.W., White, A.H. Steroids (2006) [Pubmed]
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