Fluorogenic cyanohydrin esters as chiral probes for esterase and lipase activity

被引:23
作者
Leroy, E [1 ]
Bensel, N [1 ]
Reymond, JL [1 ]
机构
[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland
关键词
enantioselectivity; enzyme assay; fluorescence; high-throughput screening; lipases;
D O I
10.1002/adsc.200303005
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Fluorogenic cyanohydrin esters were prepared that release the fluorescent product umbelliferone by secondary decomposition of the primary cyanohydrin reaction product by cyanide elimination to the aldehyde and subsequent beta-elimination. Whereas butyrate 1b and octanoate 1d show the highest reaction rates with enzymes, the highest relative rates above the non-catalyzed background reaction are achieved with pivalate 1c and benzoate le. Enantioselective reactions are detected when the conversion stabilizes at 50% of the maximum fluorescence release, and enantioselectivity is confirmed by chiral-phase HPLC analysis of the unreacted cyanohydrin ester substrate.
引用
收藏
页码:859 / 865
页数:7
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