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Communication | Regular issue | Vol 68, No. 8, 2006, pp.1571-1578
Published online, 8th June, 2006
DOI: 10.3987/COM-06-10784
Preferred Conformations of Diastereomeric N-Acyl-1-naphthylalanylprolinamides and Related Dipeptides and Their Fluorescence Quenching by Chiral Amines

Hiroki Kurosawa, Kana Bakoshi, Shozo Ichikawa, Tetsutaro Igarashi, and Tadamitsu Sakurai*

*Departmnet of Applied Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan

Abstract

Enantioselective fluorescence quenching was observed in the quenching processes of the 1-naphthylalanyl-(S)-phenylglycinamide-derived diastereomers by enantiomeric pyrrolidine-2-methanols in 1,4-dioxane at room temperature, whereas the (S)-prolinamide-derived ones exhibited only a much weaker enantioselective emission quenching under the same conditions. These findings were explained on the basis of substituent and conformational effects on the stability of a singlet exciplex formed between given diastereomer and chiral amine.