Canova-Davis E, Ramachandran J
Biochemistry. 1976 Feb 24;15(4):921-7. doi: 10.1021/bi00649a030.
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.
通过与多种取代的邻硝基苯硫酰氯反应，选择性地修饰了垂体激素促肾上腺皮质激素中的单个色氨酸残基。除了对色氨酸残基进行定量修饰外，该反应总是导致甲硫氨酸残基部分氧化为亚砜。甲硫氨酸亚砜衍生物可通过在溶剂系统1-丁醇-吡啶-0.1%乙酸（5:3:11）中在Sephadex G-50上进行分配色谱从所需产物中分离出来。因此，制备并表征了促肾上腺皮质激素的2,4-二硝基苯硫酰基、2-硝基-4-羧基苯硫酰基和2-硝基-4-氨基甲酰基苯硫酰基衍生物。还描述了从绵羊垂体中分离促肾上腺皮质激素的改进方法。讨论了天然激素及其类似物的促黑素细胞活性。
