THE DEVELOPMENT AND APPLICATION OF PHOTOSENSITIVE CAGED COMPOUNDS TO AID TIME-RESOLVED STRUCTURE DETERMINATION OF MACROMOLECULES

被引:36
作者
CORRIE, JET
KATAYAMA, Y
REID, GP
ANSON, M
TRENTHAM, DR
机构
来源
PHILOSOPHICAL TRANSACTIONS OF THE ROYAL SOCIETY A-MATHEMATICAL PHYSICAL AND ENGINEERING SCIENCES | 1992年 / 340卷 / 1657期
关键词
D O I
10.1098/rsta.1992.0063
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Rapid photochemical release of biologically active molecules, typically enzyme substrates or effectors of proteins, within crystals is likely to play an important role in time-resolved macromolecular crystallography. Photosensitive or `caged' compounds in which functional groups are protected by the 1-(2-nitrophenyl)ethyl group are potentially useful because many such compounds are efficiently and fairly rapidly photolysed (product quantum yield ca. 0.5 and photolysis rate ca. 100 s-1 for esters of weakly acidic phosphates) and have proved effective probes of physiological mechanisms. However, their availability and successful application are unlikely to be universal. and in some cases limitations may arise because of low quantum yield, a photolysis rate that is slow compared with the mechanism being studied or the toxicity of the by-product, 2-nitrosoacetophenone. 3,5-Dinitrophenyl and 3',5'-dimethoxybenzoin esters are two other potentially useful photosensitive classes of compound (Kirby & Varvoglis, J. chem. Soc. chem. Commun. 406 (1967); Sheehan et al., J. Am. chem. Soc. 93, 7222 7228 (1971); Baldwin et Tetrahedron 46, 6879-6884 (1990)). 3,5-Dinitrophenyl phosphate has a product quantum yield of 0.67 and releases P(i) at greater than 10(4) s-1. However the dinitrophenyl group is not generally photosensitive: for example the P3-3,5-dinitrophenyl ester of ATP photolyses very inefficiently at pH 7. The 3',5'-dimethoxybenzoin group is a promising photosensitive group for phosphate esters and the P3-3',5'-dimethoxybenzoin ester of ATP photolyses at greater than 10(5) s-1 at neutral pH and 20-degrees-C though with only about 4% photolysis on 347 nm pulse irradiation.
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页码:233 / 243
页数:11
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