期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 16, 期 30, 页码 9056-9067出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200903067
关键词
biocatalysis; cucurbiturils; fluorescence; inclusion compounds; sensors
资金
- Israel Science Foundation
- German-Israeli Project Cooperation (DIP)
- Institute of Catalysis Science and Technology, Technion
- Skaggs Institute for Chemical Biology
- Israel Council for Higher Education
- Schulich scholarship
4-Aminobipyridine derivatives form strong inclusion complexes with cucurbit[6]uril, exhibiting remarkably large enhancements in fluorescence intensity and quantum yields. The remarkable complexation-induced pK(a) shift (Delta pK(a) = 3.3) highlights the strong charge dipole interaction upon binding. The reversible binding phenomenon can be used for the design of switchable beacons that can be incorporated into cascades of binding networks. This concept is demonstrated herein by three different applications: 1) a switchable fluorescent beacon for chemical sensing of transition metals and other ligands; 2) direct measurement of binding constants between cucurbit[6]uril and various nonfluorescent guest molecules; and 3) quantitative monitoring of biocatalytic reactions and determination of their kinetic parameters. The latter application is illustrated by the hydrolysis of an amide catalyzed by penicillin G acylase and by the elimination reaction of a beta-caba-moyloxy ketone catalyzed by aldolase antibody 38C2.
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