Derivatization of primary amines such as amino acids and peptides with naphthalenedialdehyde (NDA) in the presence of cyanide ion yields cyanobenzo[f]-isoindole (CBI) adducts that are highly fluorescent. However, the fluorescence is seriously quenched with amines that possess more than
one primary amine site, as is the case with lysine. Although it was found that the adsorption of CBI2-lysine on a solid substrate restored the fluorescence, the reason for the solution quenching, with respect to results for mono-derivatized amines, was investigated. The experiments
to probe the quenching were based on the assumption that the mechanism responsible for quenching involved a charge-transfer (CT) excited state. Thus, it was found that the solvent properties of viscosity and polarity affected the lifetime and quantum yield of fluorescence in a manner consistent
with the proposed mechanism.
Center for Bioanalytical Research and the Department of Chemistry, the University of Kansas, Lawrence, Kansas 66045
Publication date: June 1, 1990
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