88489-22-9Relevant academic research and scientific papers
FACILE SYNTHESIS OF (2R,3R)-PHENYLALANINE -2,3-d2 AND ITS APPLICATION TO CONFORMATIONAL ANALYSIS OF GRAMICIDIN S
Tanimura, Kenjiro,Kato, Tetsuo,Waki, Michinori,Izumiya, Nobuo
, p. 3737 - 3740 (1983)
(2R,3R)-Phenylalanine-2,3-d2 was synthesized in a good yield through catalytic reduction of cyclo(-2,3-dehydrophenylalanyl-D-alanyl-) under an atmosphere of 2H2 and successive acid hydrolysis, and the amino acid was used t
Facile synthesis of (2R,3R)-phenylalanine-2,3-d2 and NMR study on deuterated gramicidin S1)
Tanimura,Kato,Waki,et al.
, p. 2193 - 2197 (2007/10/02)
(2R,3R)-Phenylalanine-2,3-d2 (D-Phe(*)) was synthesized through catalytic reduction of cyclo-(Z)-2,3-dehydrophenylalanyl-D-alanyl-) under an atmosphere of 2H2 and successive acid hydrolysis in the yield of 80% in high chiral induction. The D-Phe* thus obtained was used for synthesis of [D-Phe *4,4'] gramidicin S (GS*) gramidicin S (GS*). The 1H NMR spectrum of GS* in DMSO-d6 showed a sharp singlet at 2.98 ppm for the (3S)-proton of D-Phe* residue. It has been proposed that among rotamers of D-Phe aromatic side chain in GS the one with κ1 = 180° is predominant. The present observation provides sound evidence for assignments of D-Phe β-protons based on the proposal. (2R,3R)-phenylalanine-2,3-d//2 (d-Phe*) was synthesized through catalytic reduction of cyclo(-(Z)-2,3-dehydrophenylalanyl-D-alanyl-) under an atmosphere of **2H//2 and successive acid hydrolysis in the yield of 80% in high chiral induction. The D-Phe* thus obtained was used for synthesis of left bracket D-Phe***4**,**4** prime right bracket gramicidin S (GS*). The **1H NMR spectrum of GS* in DMSO-d//6 showed a sharp singlet at 2. 98 ppm for the (3S)-proton of D-Phe* residue. It has been proposed that among rotamers of D-Phe aromatic side chain in GS the one with // kappa //1 equals 180 degree is predominant. The present observation provides sound evidence for assignments of D-Phe beta -protons based on the proposal.
