The Intramolecular Loss of Fluorescence by Lysine Derivatized with Naphthalenedialdehyde
Year: 1990
Type: article
Abstract: 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 CBI 2 -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.
Source: Applied Spectroscopy
Institution: University of Kansas
Language: English
Subfield: Physical and Theoretical Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W2028170500