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Paper | Special issue | Vol 79, No. 1, 2009, pp.781-789
Published online, 14th November, 2008
DOI: 10.3987/COM-08-S(D)47
Use of Diketopiperazines for Determining Absolute Configurations of α-Substituted Serines by 1H-NMR Spectroscopy

Shigeki Sano,* Michiyasu Nakao, Masanori Takeyasu, Syuji Kitaike, Yasuko Yoshioka, and Yoshimitsu Nagao

*Molecular Medicinal Chemistry, Faculty of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8505, Japan

Abstract

A chiral α-substituted serine of interest was transformed into both of the corresponding diastereomers of diketopiperazines utilizing L- and D-phenylalanine methyl ester hydrochloride. The absolute configuration of the original chiral α-substituted serine was determined by 1H-NMR analyses of the resulting diastereomers.