期刊
CHEMBIOCHEM
卷 7, 期 11, 页码 1690-1695出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.200600111
关键词
caged neurtransmitters; ester protecting groups; photolysis
资金
- Medical Research Council [U117512659] Funding Source: researchfish
We report here the syntheses and the photolytic properties of 3-(4,5-dimethoxy-2-nitrophenyl)-2-butyl (DMNP8) esters as new photoremovable groups for carboxylic acids, and their use for the caging of L-glutamate. A high-yielding synthesis of the DMNP8 esters led to a 4:1 threo/erythro diastereomeric mixture, which could be separated by HPLC. While these esters were stable in neutral buffer, photolysis at 364 nm induced a >= 95 % release of the carboxylic acid, with a 0.26 quantum yield for L-glutamate formation. L-Glutamate release was also possible by two-photon photolysis with an action cross section of 0.17 GM at 720 nm. Laser photolysis at 350 nm generated a transient species at around 410 nm, attributed to a quinonoid aci-nitro intermediate that decayed in the submillisecond time range (t(1/2) = 0.53 ms) for the faster gamma-L-glutamyl threo-esters. Given the absorbance of these esters (lambda(max)=350 nm; epsilon=4500), the threo DMNPB esters represent new caging groups that can be efficiently photolyzed at near-UV wavelengths. An efficient and rapid photolytic release of L-glutamate has been demonstrated on hippocampal neurons in primary culture.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据