Diastereoselective synthesis of non-proteinogenic α-amino acids

被引:6
|
作者
Lecointe, L
Rolland, V [1 ]
Pappalardo, L
Roumestant, ML
Viallefont, P
Martinez, J
机构
[1] Univ Montpellier 1, UMR 5810, Lab Aminoacides Peptides & Prot, F-34095 Montpellier 5, France
[2] Univ Montpellier 2, Lab Aminoacides Peptides & Prot, F-34095 Montpellier, France
来源
JOURNAL OF PEPTIDE RESEARCH | 2000年 / 55卷 / 04期
关键词
asymetric synthesis; azatyrosine; 2-hydroxypinan-3-one; tribromophenylalanine; trichlorophenylalanine;
D O I
10.1034/j.1399-3011.2000.00681.x
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The synthesis of enantiomerically pure azatyrosine, tribromophenylalanine and trichlorophenylalanine is described, using two methods, diastereoselective alkylation and (or) diastereoselective protonation of chiral enolates.
引用
收藏
页码:300 / 307
页数:8
相关论文
共 50 条
  • [1] Stereoselective synthesis of non-proteinogenic amino acids
    Bowler, A. N.
    Doyle, P. M.
    Hitchcock, P. B.
    Young, D. W.
    Tetrahedron, 53 (30):
  • [2] Stereoselective synthesis of non-proteinogenic amino acids
    Bowler, AN
    Doyle, PM
    Hitchcock, PB
    Young, DW
    TETRAHEDRON, 1997, 53 (30) : 10545 - 10554
  • [3] Photochemical transformations of proteinogenic and non-proteinogenic amino acids
    Griesbeck, AG
    CHIMIA, 1998, 52 (06) : 272 - 283
  • [4] Non-proteinogenic amino acids in sarcopenia
    Chang, Yun Ching
    Chang, Sue-Joan
    ANNALS OF NUTRITION AND METABOLISM, 2023, 79 : 86 - 86
  • [5] ASYMMETRIC-SYNTHESIS OF NON-PROTEINOGENIC AMINO-ACIDS
    WEINGES, K
    CHIMIA, 1980, 34 (08) : 346 - 347
  • [6] Genetically Encoded Photocaged Proteinogenic and Non-Proteinogenic Amino Acids
    Yang, Xiaochen
    Su, Xun-Cheng
    Xuan, Weimin
    CHEMBIOCHEM, 2024, 25 (17)
  • [7] Synthesis of non-proteinogenic (D)- or (L)-amino acids by asymmetric hydrogenation
    Kreuzfeld, HJ
    Dobler, C
    Schmidt, U
    Krause, HW
    AMINO ACIDS, 1996, 11 (3-4) : 269 - 282
  • [8] Design and synthesis of non-proteinogenic amino acids and secondary structures of their peptides
    Tanaka, Masakazu
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2006, 126 (10): : 931 - 944
  • [9] SYNTHESIS OF NON-PROTEINOGENIC AMINO-ACIDS WITH 3 CHIRAL CENTERS
    BOWLER, AN
    DOYLE, PM
    HITCHCOCK, PB
    YOUNG, DW
    TETRAHEDRON LETTERS, 1991, 32 (23) : 2679 - 2682
  • [10] UPTAKE OF NON-PROTEINOGENIC AMINO ACIDS BY HIGHER PLANTS
    SCHEFFER, F
    KICKUTH, R
    ALDAG, R
    AGROCHIMICA, 1967, 11 (06): : 485 - +