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Caged NADP and NAD. Synthesis and characterization of functionally distinct caged compounds

机译：笼中的NADP和NAD。功能不同的笼状化合物的合成与表征

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Two caged NADP compounds have been synthesized and characterized for use in the crystallographic study of isocitrate dehydrogenase (IDH), as well as for general use in cell biology, metabolism, and enzymology. One caged NADP compound has been designed to be "catalytically caged" so that it can bind to IDH prior to photolysis but is not catalytically active. A second NADP compound is "affinity caged" so that addition of the caging group inhibits binding of the compound to IDH prior to photolysis. The catalytically caged compound was synthesized in a two-step process, starting with the NADase-catalyzed exchange of a synthetic nicotinamide derivative onto NADP. X-ray structures of the NADP compounds with IDH show the catalytically caged NADP bound to the enzyme with its nicotinamide group improperly positioned to allow turnover, while the affinity caged NADP does not bind to the enzyme at concentrations up to 50 mM. Two analogous caged NAD compounds have also been synthesized. The NADP and NAD compounds were characterized in terms of kinetics, quantum yield, and product formation. The affinity caged NADP compound P2'-[1-(4,5-dimethoxy-2-nitrophenyl)ethyl] NADP (VIII) is photolyzed at a rate of 1.8 x 10(4) s-1 with a quantum yield of 0.19 at pH 7; the NAD analog P-[1-(4,5-dimethoxy-2-nitrophenyl)ethyl] NAD (IX) is photolyzed at at a rate of 1.7 x 10(4) s-1 with a quantum yield of 0.17.
机译：已经合成了两种笼状的NADP化合物，并进行了表征，可用于异柠檬酸脱氢酶（IDH）的晶体学研究，以及细胞生物学，代谢和酶学中的常规用途。一种笼状NADP化合物已被设计为“催化笼状”，因此它可以在光解之前与IDH结合，但没有催化活性。第二种NADP化合物是“亲和笼”的，因此在光解之前添加笼基会抑制化合物与IDH的结合。从NADase催化的合成烟酰胺衍生物到NADP的NADase催化交换开始，分两步合成了催化笼状化合物。带有IDH的NADP化合物的X射线结构显示，与该酶结合的催化笼状NADP的烟酰胺基位置不正确，无法进行周转，而在高达50 mM的浓度下，亲和笼状NADP则不与该酶结合。还合成了两种类似的笼状NAD化合物。通过动力学，量子产率和产物形成来表征NADP和NAD化合物。笼罩有亲和力的NADP化合物P2'-[1-（4,5-二甲氧基-2-硝基苯基）乙基] NADP（VIII）以1.8 x 10（4）s-1的速率进行光解，量子产率为0.19。 pH值7; NAD类似物P- [1-（4,5-二甲氧基-2-硝基苯基）乙基] NAD（IX）以1.7 x 10（4）s-1的速率光解，量子产率为0.17。

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