Facile synthesis of (2R,3R)-phenylalanine-2,3-d2 and NMR study on deuterated gramicidin S.
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概要
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(2<I>R</I>,3<I>R</I>)-Phenylalanine-2,3-<I>d</I><SUB>2</SUB> (D-Phe<SUP>*</SUP>) was synthesized through catalytic reduction of <I>cyclo</I>(-(<I>Z</I>)-2,3-dehydrophenylalanyl-D-alanyl-) under an atmosphere of <SUP>2</SUP>H<SUB>2</SUB> and successive acid hydrolysis in the yield of 80% in high chiral induction. The D-Phe<SUP>*</SUP> thus obtained was used for synthesis of [D-Phe<SUP>*4,4′</SUP>] gramicidin S (GS<SUP>*</SUP>). The <SUP>1</SUP>H NMR spectrum of GS<SUP>*</SUP> in DMSO-<I>d</I><SUB>6</SUB> showed a sharp singlet at 2.98 ppm for the (3<I>S</I>)-proton of D-Phe<SUP>*</SUP> residue. It has been proposed that among rotamers of D-Phe aromatic side chain in GS the one with κ<SUB>1</SUB>=180° is predominant. The present observation provides sound evidence for assignments of D-Phe β-protons based on the proposal.
- 公益社団法人 日本化学会の論文
著者
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Waki Michinori
Laboratory Of Biochemistry Department Of Chemistry Faculty Of Science Kyushu University
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Lee Sannamu
Laboratory Of Biochemistry Faculty Of Science Kyushu University
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Izumiya Nobuo
Laboratory Of Biochemistry Faculty Of Engineering Kyushu Sangyo University
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KATO Tetsuo
Laboratory of Biochemistry, Faculty of Science, Kyushu University
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Waki Michinori
Laboratory of Biochemistry, Faculty of Science, Kyushu University 33
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Tanimura Kenjiro
Laboratory of Biochemistry, Faculty of Science, Kyushu University 33
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Kodera Yasushi
Department of Chemistry, Faculty of Science, Fukuoka University
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Kato Tetsuo
Laboratory of Biochemistry, Faculty of Science 33, Kyushu University
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