Chemical modification of the tryptophan residue in adrenocorticotropin

Canova-Davis, Eleanor ; Ramachandran, J. (1976) Chemical modification of the tryptophan residue in adrenocorticotropin Biochemistry, 15 (4). pp. 921-927. ISSN 0006-2960

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The single tryptophan residue in the pituitary hormone adrenocorticotropin was modified selectively by reaction with a variety of substituted o-nitrophenylsulfenyl chlorides. In addition to quantitative modification of the tryptophan residue, the reaction invariably resulted in partial oxidation of the methionine residue to the sulfoxide. The methionine sulfoxide derivative could be separated from the desired product by partition chromatography on Sephadex G-50 in the solvent system 1-butanol-pyridine-0.1% acetic acid (5:3:11). Thus, the 2,4-dinitrophenylsulfenyl, 2-nitro-4-carboxyphenylsulfenyl, and 2-nitro-4-carbamidophenylsulfenyl derivatives of adrenocorticotropin were prepared and characterized. Modifications in the isolation of adrenocorticotropin from ovine pituitaries are also described. The melanocyte stimulating activities of the native hormone and the analogues are discussed.

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Source:Copyright of this article belongs to American Chemical Society.
ID Code:40950
Deposited On:25 May 2011 10:21
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