P1,P4-双(5'-腺苷)四磷酸的立体化学定义的膦酸酯和硫代磷酸酯类似物的合成及其对酶促水解的抗性
Synthesis and resistance to enzymic hydrolysis of stereochemically-defined phosphonate and thiophosphate analogues of P1,P4-bis(5'-adenosyl) tetraphosphate.
作者信息
Blackburn G M, Taylor G E, Thatcher G R, Prescott M, McLennan A G
机构信息
Department of Chemistry, University of Sheffield, UK.
出版信息
Nucleic Acids Res. 1987 Sep 11;15(17):6991-7004. doi: 10.1093/nar/15.17.6991.
Abstract
Novel analogues of P1,P4-bis(5'-adenosyl) tetraphosphate, Ap4A (1), have been prepared with sulphur substituents at P1 and P4 and either oxygen or methylene bridges at the P2,P3-position. Separation of three isomers of the ApspCH2ppsA species has been achieved by a combination of mplc and hplc and the Rp,Rp, Rp,Sp, and Sp,Sp diastereoisomers identified on the basis of selective enzymatic hydrolysis using snake venom phosphodiesterase. Each of these three isomers is a strong competitive inhibitor of the specific Ap4Aase from Artemia and is highly resistant to the asymmetric cleavage normally catalysed by this enzyme.
摘要
已制备出P1,P4-双(5'-腺苷)四磷酸（Ap4A，1）的新型类似物，其在P1和P4位带有硫取代基，在P2,P3位带有氧或亚甲基桥。通过中压液相色谱（mplc）和高效液相色谱（hplc）相结合的方法实现了ApspCH2ppsA物种三种异构体的分离，并基于使用蛇毒磷酸二酯酶的选择性酶促水解鉴定出Rp,Rp、Rp,Sp和Sp,Sp非对映异构体。这三种异构体中的每一种都是卤虫特异性Ap4A酶的强竞争性抑制剂，并且对该酶通常催化的不对称切割具有高度抗性。
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