Design and use of fluorogenic aldehydes for monitoring the progress of aldehyde transformations.
We describe the first examples of fluorogenic aldehydes useful for monitoring many types of reactions including aldol reactions, allylations, and reductions. The fluorogenic aldehydes were constructed by covalent combination of a fluorophore and an aldehyde moiety via a linker. In the resulting single molecule, the aldehyde functioned as a quencher of the fluorophore's fluorescence. The reaction product, modified at the aldehyde functionality, no longer served as an effective quencher. The reaction products showed up to approximately 80-fold higher fluorescence than the aldehyde reactants.
Tanaka
Fujie
F
The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. ftanaka@scripps.edu
Mase
Nobuyuki
N
Barbas
Carlos F
CF
D000426:Alcohol Dehydrogenase / Q000378:metabolism; D000447:Aldehydes / Q000737:chemistry* / Q000378:metabolism; D001711:Biotransformation; D002384:Catalysis; D003013:Clostridium / Q000201:enzymology; D005456:Fluorescent Dyes / Q000737:chemistry*; D015394:Molecular Structure
D000447:Aldehydes; D005456:Fluorescent Dyes; C116609:3-hydroxybutanal; D000426:Alcohol Dehydrogenase