Asymmetric synthesis of .ALPHA.-deuterated .ALPHA.-amino acids through nonenzymatic transamination reaction and the determination of their enantiomeric excesses.
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概要
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Optically active α-deuterated α-amino acids were prepared in methano-<I>d</I> through Zn<SUP>2+</SUP>-catalyzed transamination reaction between the chiral pyridoxamine analogs, (<I>R</I>)- or (<I>S</I>)-15-aminomethyl-14-hydroxy-5,5-dimethyl-2,8-dithia[9] (2,5)pyridinophane and various α-keto acids with enantiomeric excesses ranging from 40 to 94%. Aliphatic α-keto acids gave α-deuterated α-amino acids, whereas aromatic ones possessing a methylene group between the carbonyl group (ketone) and the aromatic ring underwent concomitant deuterium substitution at the active methylene group to give the amino acids deuterated at both α- and β-positions of the carboxyl group. The use of the (<I>S</I>)-pyridoxamine analog gave the (<I>R</I>)-deuterated α-amino acids in excess and <I>vice versa</I>. The enatiomeric excesses of the amino acids were determined through the analyses of <SUP>1</SUP>H NMR spectra of the Schiff bases produced by the condensation of the amino acids with the chiral pyridoxal analog, (<I>R</I>)- or (<I>S</I>)-15-formyl-14-hydroxy-2,8-dithia[9](2, 5)pyridinophane. The azomethine protons of the diastereomeric Schiff bases were clearly resolved in the spectrum and their intensities well reflected the amount of the diastereomers.
- 公益社団法人 日本化学会の論文
著者
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Ando Makoto
The Institute of Physical and Chemical Research
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Kuzuhara Hiroyoshi
The Institute of Physical and Chemical Research
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Tachibana Yoji
The Institute of Physical and Chemical Research
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