Aerial oxidation of the glucocorticoid side-chain under pH control

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

doi:10.1016/j.steroids.2005.08.003

Aerial oxidation of the glucocorticoid side-chain under pH control

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

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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. (c) 2005 Elsevier Inc. All rights reserved.

Original language	English
Pages (from-to)	34-41
Journal	Steroids
Volume	71
Issue number	1
DOIs	https://doi.org/10.1016/j.steroids.2005.08.003
Publication status	Published - 2006

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title = "Aerial oxidation of the glucocorticoid side-chain under pH control",

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. (c) 2005 Elsevier Inc. All rights reserved.",

author = "J.S. Edmonds and M. Morita and P. Turner and Brian Skelton and Allan White",

year = "2006",

doi = "10.1016/j.steroids.2005.08.003",

language = "English",

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journal = "Steroids",

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T1 - Aerial oxidation of the glucocorticoid side-chain under pH control

AU - Edmonds, J.S.

AU - Morita, M.

AU - Turner, P.

AU - Skelton, Brian

AU - White, Allan

PY - 2006

Y1 - 2006

N2 - 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.

AB - 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.

U2 - 10.1016/j.steroids.2005.08.003

DO - 10.1016/j.steroids.2005.08.003

M3 - Article

SN - 0039-128X

VL - 71

SP - 34

EP - 41

JO - Steroids

JF - Steroids

IS - 1

ER -

Aerial oxidation of the glucocorticoid side-chain under pH control

Abstract

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