title: Design and use of fluorogenic aldehydes for monitoring the progress of aldehyde transformations.
abstract: 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.
authors.affiliation: 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
authors.forename: Fujie
authors.initials: F
authors.lastname: Tanaka
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Mase
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: 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
chemical_list: D000447:Aldehydes; D005456:Fluorescent Dyes; C116609:3-hydroxybutanal; D000426:Alcohol Dehydrogenase