Fluorescent detection of carbon-carbon bond formation.
We have developed a new spectroscopic system for detecting carbon-carbon bond formation by fluorescence to enhance high-throughput catalyst screening and rapid characterization of catalysts on a small scale. Fluorogenic substrates composed of a fluorophore possessing an amino group are readily prepared as amides of alpha,beta-unsaturated carbonyl compounds and generally exhibit low fluorescence, while Michael or Diels-Alder reactions of these fluorogenic substrates provide products of significantly increased fluorescence. The product's fluorescence is approximately 20- to 100-fold higher than that of the substrate. The assay system was validated by screening potential catalysts of the Michael reaction and in solvent optimization experiments. The covalent combination of fluorophores possessing an amino group with alpha,beta-unsaturated carbonyl compounds should provide a diverse range of fluorogenic substrates that may be used to rapidly screen catalysts and to optimize reaction conditions.
Tanaka
Fujie
F
The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. ftanaka@scripps.edu
Thayumanavan
Rajeswari
R
Barbas
Carlos F
CF
D000096:Acetone / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000595:Amino Acid Sequence; D005634:Fructose-Bisphosphate Aldolase / Q000737:chemistry; D008969:Molecular Sequence Data; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000737:chemistry; D010446:Peptide Fragments / Q000737:chemistry; D013050:Spectrometry, Fluorescence / Q000379:methods*
D000577:Amides; D000588:Amines; D009930:Organic Chemicals; D010446:Peptide Fragments; D000096:Acetone; D005634:Fructose-Bisphosphate Aldolase