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Tetrahedron Letters
Volumn 20, Issue 46, 1979, Pages 4483-4486
Efficient asymmetric synthesis of α-amino acids through hydrogenation of α,β-dehydroamino acid residue in cyclic dipeptides
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EID: 0000666444     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(01)86625-9     Document Type: Article
Times cited : (41)
References (13)
  • 7
    • 84918026161 scopus 로고    scopus 로고
    • Ratio of diastereomeric isomers obtained by hydrogenation of cyclo(ΔTrp-L-Ala) or cyclo (ΔTrp-L-Leu) was directly determined by Hitachi model 635A high performance liquid chromatograph.
  • 8
    • 84918026160 scopus 로고    scopus 로고
    • We assume that 9 will be obtained from cyclo(L-Trp-L-Leu) by the action of an enzyme isolated from Pseudomonus. Y. Noda, K. Takai, T. Tokuyama, H. Narumiya, H. Ushiro and O. Hayaishi (J. Biol. Chem., 252, 4413, 1977)) isolated the enzyme, and observed that the enzyme catalyses the formation of ΔTrp residue from L-Trp residue in many peptides.
  • 9
    • 84918026159 scopus 로고    scopus 로고
    • We observed that the mixture of cyclo(Trp-L-Leu) possesses a bitter taste in threshold value of 0.015 mg/ml; cyclo(ΔTrp-L-Leu) and an authentic cyclo(L-Trp-L-Leu) showed exactly the same bitterness. A. Yasutake, K. Miyazaki, H. Aoyagi, T. Kato and N. Izumiya (FEBS Lett. 100, 241, 1979)) reported that both diastereomeric cyclo (L-Trp-L-Hmp) (Hmp=2=hydroxy-4-methylpentanoic acid) and cyclo (L-Trp-D-Hmp) possess the same bitterness. T. Shiba and K. Nunami (Tetrahedron Lett., 509 (1974)) elucidated the structure of a bitter principle in nature as cyclo (L-Trp-L-Leu).

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