牛肾上腺雌激素硫酸转移酶的研究。III. 3'-磷酸腺苷5'-磷酸硫酸酯和2'-磷酸腺苷5'-磷酸硫酸酯的简便合成。

Studies on bovine adrenal estrogen sulfotransferase. III. Facile synthesis of 3'-phospho- and 2'-phosphoadenosine 5'-phosphosulfate.

作者信息

Horwitz J P, Neenan J P, Misra R S, Rozhin J, Huo A, Philips K D

出版信息

Biochim Biophys Acta. 1977 Feb 9;480(2):376-81. doi: 10.1016/0005-2744(77)90030-4.

Abstract

A practical synthesis of 3'-phosphoadenosine 5'-phosphosulfate (IV) in yields of 68-72% from adenosine 2',3'-cyclic phosphate 5'-phosphate (II) is described. Reaction of II with triethylamine-N-sulfonic acid affords adenosine 2',3'-cyclic phosphate 5'-phosphosulfate (III) which, on treatment with ribonuclease-T2, provides IV. Spleen phosphodiesterase, on the other hand, converts III to 2'-phosphoadenosine 5'-phosphosulfate (V). The biological activity of IV, measured by sulfate transfer to [6,7-3H2]estrone as mediated by bovine adrenal estrone sulfotransferase (3'-phosphoadenylyl-sulfate:estrone 3-sulfotransferase, EC 2.8.2.4), is identical with that obtained with a sample of IV prepared by an established biochemical procedure. By contrast, V exhibits approximately one-third the activity of the natural isomer.

摘要

描述了一种从2',3'-环磷酸腺苷5'-磷酸（II）以68 - 72%的产率实际合成3'-磷酸腺苷5'-磷酸硫酸酯（IV）的方法。II与三乙胺 - N - 磺酸反应得到2',3'-环磷酸腺苷5'-磷酸硫酸酯（III），用核糖核酸酶 - T2处理III可得IV。另一方面，脾磷酸二酯酶将III转化为2'-磷酸腺苷5'-磷酸硫酸酯（V）。通过牛肾上腺雌酮硫酸转移酶介导的将硫酸转移至[6,7 - 3H₂]雌酮来测定IV的生物活性（3'-磷酸腺苷酰硫酸：雌酮3 - 硫酸转移酶，EC 2.8.2.4），其与通过既定生化程序制备的IV样品所获得的活性相同。相比之下，V的活性约为天然异构体的三分之一。