Chemoenzymatic synthesis of the two enantiomers of 7-azatryptophan

被引:18
|
作者
Lecointe, L [1 ]
Rolland-Fulcrand, V [1 ]
Roumestant, ML [1 ]
Viallefont, P [1 ]
Martinez, J [1 ]
机构
[1] Univ Montpellier 1&2, Lab Aminoacides Peptides & Prot, F-34095 Montpellier 5, France
关键词
D O I
10.1016/S0957-4166(98)00130-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
7-Azatryptophan is an unnatural alpha-amino acid with a very potent fluorescent activity. It is used as a vehicle for probing the structure and dynamics of proteins and peptides. Diastereoselective alkylation, diastereoselective protonation and enzymatic resolution have been tested for preparing enantiomerically pure 7-azatryptophan. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1753 / 1758
页数:6
相关论文
共 50 条
  • [1] TIME-RESOLVED FLUORESCENCE OF ENANTIOMERS OF MODEL PEPTIDES CONTAINING 7-AZATRYPTOPHAN
    ITO, A
    BRENNAN, JD
    JULIANO, L
    MORT, JS
    PAIVA, A
    SZABO, AG
    BIOPHYSICAL JOURNAL, 1994, 66 (02) : A298 - A298
  • [2] Interrogating interactions of 7-azatryptophan with micelles.
    Kelepouris, L
    Blanchard, GJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U82 - U82
  • [3] THE PHOTOPHYSICAL PROBE, 7-AZATRYPTOPHAN, IN SYNTHETIC PEPTIDES
    RICH, RL
    NEGRERIE, M
    LI, J
    ELLIOTT, S
    THORNBURG, RW
    PETRICH, JW
    PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1993, 58 (01) : 28 - 30
  • [5] FLUORESCENT SPECIES OF 7-AZAINDOLE AND 7-AZATRYPTOPHAN IN WATER
    CHEN, Y
    RICH, RL
    GAI, F
    PETRICH, JW
    JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (09): : 1770 - 1780
  • [6] Using 7-azatryptophan to probe protein structure and dynamics
    Petrich, JW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 193 - PHYS
  • [7] 7-AZAINDOLE .1. SYNTHESIS AND CONVERSION TO 7-AZATRYPTOPHAN AND OTHER DERIVATIVES
    ROBISON, MM
    ROBISON, BL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (02) : 457 - 460
  • [8] SYNTHESIS OF BETA-GALACTOSIDASE IN ESCHERICHIA-COLI IN PRESENCE OF 7-AZATRYPTOPHAN
    JANECEK, J
    SPIZEK, J
    FOLIA MICROBIOLOGICA, 1969, 14 (06) : 529 - &
  • [9] ALTERATION IN HETEROCYST PATTERN OF ANABAEMA PRODUCED BY 7-AZATRYPTOPHAN
    MITCHISON, GJ
    WILCOX, M
    NATURE-NEW BIOLOGY, 1973, 246 (155): : 229 - 233
  • [10] USING 7-AZATRYPTOPHAN TO PROBE SMALL MOLECULE-PROTEIN INTERACTIONS ON THE PICOSECOND TIME-SCALE - THE COMPLEX OF AVIDIN AND BIOTINYLATED 7-AZATRYPTOPHAN
    RICH, RL
    GAI, F
    LANE, JW
    PETRICH, JW
    SCHWABACHER, AW
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (02) : 733 - 739