THE SYNTHESIS AND METAL-BINDING CHARACTERISTICS OF NOVEL, ISOPOLAR PHOSPHONATE ANALOGS OF NUCLEOTIDES
THE SYNTHESIS AND METAL-BINDING CHARACTERISTICS OF NOVEL, ISOPOLAR PHOSPHONATE ANALOGS OF NUCLEOTIDES
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DOI：
10.1039/p19840001119
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发表时间：
1984-01-01
期刊：
影响因子：
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通讯作者：
KOLKMANN, F
中科院分区：
文献类型：
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作者：
BLACKBURN, GM;KENT, DE;KOLKMANN, F
二氯亚甲基-、二氟亚甲基-和氟亚甲基-双膦酸与腺苷和鸟苷的5“-磷酰吗啉缩合，得到ATP和GTP的核苷酸类似物，它们是等极性和等排的。一种等极性但非等排的ATP类似物是由乙炔-1，2-二膦酸与AMP-吗啉酯缩合而得。31 P NMR和pKa数据表明，在系列CH 2 CFH < CF2 <C < O，相对于β，.伽马桥接功能对二价金属Mg、Ca、Zn和Ba的结合的NMR和离子选择性电极测量表明，金属阳离子与核苷酸四阴离子结合的模式响应于膦酸酯的空间和电子特征，其中β，伽马二氟亚甲基类似物最接近ATP。
Dichloromethylene-, difluoromethylene- and fluoromethylene-bisphosphonic acids condense with the 5''-phosphoromorpholidates of adenosine and guanosine to give nucleotide analogs of ATP and GTP which are isopolar and isosteric. An isopolar but non-isosteric analog of ATP results from the condensation of acetylene-1,2-bisphosphonic acid with AMP-morpholidate. 31P NMR and pKa data show that the physical analogy improves in the series CH2 < CCl2 .ltoreq. CFH < CF2 < C.tbd.C < O with respect to the .beta.,.gamma.-bridging function. NMR and ion-selective electrode measurements on the binding of the divalent metals Mg, Ca Zn and Ba suggest that the pattern of metal cation binding to the nucleotide tetra-anion responds both to steric and to electronic features of the phosphonates, with the .beta.,.gamma.-difluoromethylene analog most closely resembling ATP.