'CAGED' COMPOUNDS TO PROBE THE DYNAMICS OF CELLULAR PROCESSES: SYNTHESIS AND PROPERTIES OF SOME NOVEL PHOTOSENSITIVE P-2-NITROBENZYL ESTERS OF NUCLEOTIDES
'CAGED' COMPOUNDS TO PROBE THE DYNAMICS OF CELLULAR PROCESSES: SYNTHESIS AND PROPERTIES OF SOME NOVEL PHOTOSENSITIVE P-2-NITROBENZYL ESTERS OF NUCLEOTIDES
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“笼”化合物探测细胞过程的动力学：一些新型光敏核苷酸 P-2-硝基苄酯的合成和性质
DOI：
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发表时间：
1989
期刊：
影响因子：
--
通讯作者：
D. Trentham
中科院分区：
文献类型：
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作者：
J. F. Wootton;D. Trentham
底物或调节分子的光化学释放是一种发展中的技术，其克服了诸如涉及大分子组装的生物过程的动力学研究中的扩散延迟的问题。广泛的磷酸酯如核苷酸和核苷酸类似物可以在其磷酸酯基团上用1-（2-硝基苯基）重氮乙烷和1-（3，4-二甲氧基-6-硝基苯基）重氮乙烷烷基化。如此形成的磷酸酯通常是生物惰性的，并且可以用近UV（300-360 nm）照射光解为起始材料。用脉冲激光或弧光灯对这些“笼状”化合物进行闪光光解，释放出高达几毫摩尔的生物活性化合物。在光子吸收之后，在活性化合物释放之前，笼状化合物内发生暗反应，并且需要测量这些过程的速率来确定该技术的时间分辨率。核苷3′，5 ′-环磷酸的β-l-（2-硝基苯基）乙酯在pH 7和11 M离子强度的水溶液中于21°C下在5 s/min光解。在pH 7以下，光解是酸催化的。Pi和ATP的β-1-（3，4-二甲氧基-6-硝基苯基）乙酯比相应的β-1-（2-硝基苯基）乙酯更慢地光解。环核苷酸的β-1-（3，4-二甲氧基-6-硝基苯基）乙酯在pH 7的水中不稳定。然而，环核苷酸的β-1-（3，4-二甲氧基-6-硝基苄基）酯似乎比它们的β-1-（2-硝基苄基）酯对应物更快地光解，尽管具有低的量子产率。这些结果的影响的光解机制和2-硝基苄基磷酸酯在生物研究中的应用进行了讨论。
Photochemical release of substrates or regulatory molecules is a developing technique that overcomes problems such as diffusional delays in the kinetic study of biological processes involving macromolecular assemblies. A wide range of phosphate esters such as nucleotides and nucleotide analogues can be alkylated on their phosphate groups with 1-(2-nitrophenyl)diazoethane and l-(3,4- dimethoxy-6-nitrophenyl)diazoethane. The phosphate esters so formed are generally biologically inert and may be photolyzed to starting material with near-UV (300-360 nm) irradiation. Flash photolysis of these ‘caged’ compounds with a pulsed laser or arc lamp releases up to several millimolar of a biologically active compound. Subsequent to photon absorption, dark reactions occur within the caged compounds before the active compound is released and measurement of the rate of these processes is necessary to determine the time resolution of the technique. P-l-(2-Nitrophenyl)ethyl esters of nucleoside 3′,5′-cyclic phosphates photolyze at 5 s∓1 at 21°C in aqueous solution at pH 7 and 11 M ionic strength. Below pH 7 the photolysis is acid catalyzed. P-l-(3,4-dimethoxy-6-nitrophenyl)ethyl esters of Pi and ATP photolyze more slowly than the corresponding P-l-(2-nitrophenyl)ethyl esters. The P-1-(3,4-dimethoxy-6-nitrophenyl)ethyl esters of cyclic nucleotides are unstable in water at pH 7. However the P-l-(3,4- dimethoxy-6-nitrobenzyl)esters of cyclic nucleotides appear to photolyze more rapidly than their P-1-(2-nitrobenzyl)ester counterparts, though with low quantum yield. The implications of these results for the photolysis mechanisms and the application of 2- nitrobenzyl phosphate esters in biological research is discussed.
通过时间分辨 X 射线衍射，在 16 A 分辨率下，由酶磷酸化至 E1 大约 P 诱导肌质网膜轮廓的变化。
影响因子：
3.4
作者：
Pascolini,D;Herbette,LG;Skita,V;Asturias,F;Scarpa,A;Blasie,JK
通讯作者：
Blasie,JK
DOI：
10.1073/pnas.77.12.7237
发表时间：
1980-01-01
期刊：
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES
影响因子：
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作者：
MCCRAY, JA;HERBETTE, L;TRENTHAM, DR
通讯作者：
TRENTHAM, DR