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Zenichi Yoshida (1925-2023)

Professor. Zenichi Yoshida,
a member of the Honorary Advisors of HETEROCYCLES (1975-1998),
has passed away on May 4, 2023 at the age of 97.
I deeply express my regret over his death.
Kunio Ogasawara
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May 11, 2023
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■ Enantioselective Fluorescence Recognition of Chiral Amines by N-Acyl-(S)-1-naphthylalanyl-(S)-phenylglycine and N-Acyl-(S)-1-naphthylalanyl-(S)-1-naphthylalanine Dipeptides Bridged by a 1,2-Phenylene or an Ethylene Spacer Chain
Tomoe Ishikawa, Miho Sonobe, Akinori Hayakawa, Tetsutaro Igarashi, and Tadamitsu Sakurai*
*Department of Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan
Abstract
This study sought to support the development of enantioselective dipeptide fluorescence sensors by examining the ability of the N-acyl-(S)-1-naphthylalanyl-(S)-phenylglycine and N-acyl-(S)-1-naphthylalanyl-(S)-1-naphthylalanine dipeptides (bridged by the 1,2-phenylene or ethylene spacer chain) to discriminate between aliphatic amine-derived (S)- and (R)-enantiomers. The results indicated that both hydrogen-bonding interactions in the ground state and charge-transfer interactions in the excited state are involved in the fluorescence quenching of these bridged dipeptides by chiral amines to produce the upward curving Stern–Volmer plots. In addition, the numerical analysis of these plots led to the conclusion that the bridged naphthylalanylphenylglycine dipeptide shows the highest ability to differentiate the (S)-enantiomer from (R)-enantiomer when the emission of this dipeptide is quenched by chiral alaninols.
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