Direct STD NMR Identification of β-Galactosidase Inhibitors from a Virtual Dynamic Hemithioacetal System

被引:88
作者
Caraballo, Remi [1 ]
Dong, Hai [1 ]
Ribeiro, Joao P. [2 ]
Jimenez-Barbero, Jesus [2 ]
Ramstrom, Olof [1 ]
机构
[1] Royal Inst Technol, KTH, Dept Chem, S-10044 Stockholm, Sweden
[2] Ctr Invest Biol, Madrid 28040, Spain
基金
瑞典研究理事会;
关键词
beta-galactosidase; dynamic chemistry; hemithioacetals; inhibition; NMR spectroscopy; COMBINATORIAL LIBRARIES; LIGAND-BINDING; LIVING CELLS; ACTIVE-SITE; CHEMISTRY; ALDEHYDES; DECOMPOSITION; AMPLIFICATION; DISULFIDES; RESOLUTION;
D O I
10.1002/anie.200903920
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) The formation of a dynamic hemithioacetal system and its application toward the discovery of ß-galactosidase inhibitors were successfully investigated. The designed dynamic system, which has a virtual character in neutral aqueous media, was subjected to a direct in situ identification of the best inhibitors by 1H STD NMR spectroscopy (ONPC : o-nitrophenyl-β-galactopyranoside). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:589 / 593
页数:5
相关论文
共 73 条
  • [1] Tandem driven dynamic combinatorial resolution via Henry-iminolactone rearrangement
    Angelin, Marcus
    Vongvilai, Pornrapee
    Fischer, Andreas
    Ramstrom, Olof
    [J]. CHEMICAL COMMUNICATIONS, 2008, (06) : 768 - 770
  • [2] Self-sorting of equilibrating metallosupramolecular DCLs via constitutional crystallization
    Barboiu, Mihail
    Dumitru, Florina
    Legrand, Yves-Marie
    Petit, Eddy
    van der Lee, Arie
    [J]. CHEMICAL COMMUNICATIONS, 2009, (16) : 2192 - 2194
  • [3] BASE-CATALYZED HEMITHIOACETAL DECOMPOSITION AT A DIFFUSION-CONTROLLED RATE
    BARNETT, R
    JENCKS, WP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (23) : 5963 - &
  • [4] DIFFUSION-CONTROLLED AND CONCERTED BASE CATALYSIS IN DECOMPOSITION OF HEMITHIOACETALS
    BARNETT, RE
    JENCKS, WP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (24) : 6758 - &
  • [5] INHIBITION OF PAPAIN BY N-ACYL-AMINOACETALDEHYDES AND N-ACYL-AMINOPROPANONES - EVIDENCE FOR HEMITHIOACETAL FORMATION BY A CROSS-SATURATION TECHNIQUE IN NMR-SPECTROSCOPY
    BENDALL, MR
    CARTWRIGHT, IL
    LOWE, G
    NURSE, D
    CLARK, PI
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1977, 79 (01): : 201 - 209
  • [6] Tailored Polymer-Supported Templates in Dynamic Combinatorial Libraries: Simultaneous Selection, Amplification and Isolation of Synthetic Receptors
    Besenius, Pol
    Cormack, Peter A. G.
    Liu, Jingyuan
    Otto, Sijbren
    Sanders, Jeremy K. M.
    Sherrington, David C.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (29) : 9006 - 9019
  • [7] Bugaut A., 2008, ANGEW CHEM INT EDIT, V120, P2717
  • [8] Exploring the differential recognition of DNA G-quadruplex targets by small molecules using dynamic combinatorial chemistry
    Bugaut, Anthony
    Jantos, Katja
    Wietor, Jean-Luc
    Rodriguez, Raphael
    Sanders, Jeremy K. M.
    Balasubramanian, Shankar
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (14) : 2677 - 2680
  • [9] Phosphine-catalyzed disulfide metathesis
    Caraballo, Remi
    Rahm, Martin
    Vongvilai, Pornrapee
    Brinck, Tore
    Ramstrom, Olof
    [J]. CHEMICAL COMMUNICATIONS, 2008, (48) : 6603 - 6605
  • [10] Deracemization of a dynamic combinatorial library induced by (-)-cytidine and (-)-2-thiocytidine
    Chung, Mee-Kyung
    Hebling, Christine M.
    Jorgenson, James W.
    Severin, Kay
    Lee, Stephen J.
    Gagne, Michel R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (35) : 11819 - 11827