Mimicking the active site of aldehyde dehydrogenases: stabilization of carbonyl hydrates through hydrogen bonds

被引:8
|
作者
Roth, A. J. K. [1 ]
Tretbar, M. [1 ]
Stark, C. B. W. [1 ]
机构
[1] Univ Hamburg, Inst Organ Chem, Fachbereich Chem, D-20146 Hamburg, Germany
关键词
CELLULOSE ORGANIC-SOLVENTS; CARBOXYLIC-ACIDS; PRIMARY ALCOHOLS; N-OXIDE; CRYSTAL-STRUCTURE; TETRAPROPYLAMMONIUM PERRUTHENATE; HISTIDINOL DEHYDROGENASE; CATALYTIC MECHANISM; SELECTIVE OXIDATION; MOLECULAR-DYNAMICS;
D O I
10.1039/c5cc02831k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Aldehyde hydrates are important but highly unstable, transient intermediates in biological and synthetic oxidations to carboxylic acids. We here report N-oxides as the first class of chemical reagents capable of stabilizing such water adducts. This stabilizing effect (studied in solution and in the solid state) seems to be based on the formation of hydrogen bonds.
引用
收藏
页码:14175 / 14178
页数:4
相关论文
共 37 条
  • [1] Selectively inhibiting the active site cysteine of aldehyde dehydrogenases
    Kimble-Hill, Ann C.
    Parajuli, Bibek
    Chen, Che-Hong
    Mochly-Rosen, Daria
    Hurley, Thomas D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [2] Nicotinamide Cofactors Suppress Active-Site Labeling of Aldehyde Dehydrogenases
    Stiti, Naim
    Chandrasekar, Balakumaran
    Strubl, Laura
    Mohammed, Shabaz
    Bartels, Dorothea
    van der Hoorn, Renier A. L.
    ACS CHEMICAL BIOLOGY, 2016, 11 (06) : 1578 - 1586
  • [3] Stabilization of ketone and aldehyde enols by formation of hydrogen bonds to phosphazene enolates and their aldol products
    Kolonko, Kristopher J.
    Reich, Hans J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (30) : 9668 - +
  • [4] Microsolvation of myrtenal studied by microwave spectroscopy highlights the role of quasi-hydrogen bonds in the stabilization of its hydrates
    Chrayteh, Mhamad
    Huet, Therese R.
    Drean, Pascal
    JOURNAL OF CHEMICAL PHYSICS, 2020, 153 (10):
  • [5] Mediated coadsorption at the liquid-solid interface: Stabilization through hydrogen bonds
    Kampschulte, L
    Griessl, S
    Heckl, WM
    Lackinger, M
    JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (29): : 14074 - 14078
  • [6] Differences in the roles of conserved glutamic acid residues in the active site of human class 3 and class 2 aldehyde dehydrogenases
    Mann, CJ
    Weiner, H
    PROTEIN SCIENCE, 1999, 8 (10) : 1922 - 1929
  • [7] Stabilization of calcium- and terbium-carboxylate bonds by NH•••O hydrogen bonds in a mononuclear complex:: A functional model of the active site of calcium-binding proteins
    Onoda, A
    Yamada, Y
    Nakayama, Y
    Takahashi, K
    Adachi, H
    Okamura, TA
    Nakamura, A
    Yamamoto, H
    Ueyama, N
    Vyprachticky, D
    Okamoto, Y
    INORGANIC CHEMISTRY, 2004, 43 (14) : 4447 - 4455
  • [8] Crystallographic evidence for active-site dynamics in the hydrolytic aldehyde dehydrogenases. Implications for the deacylation step of the catalyzed reaction
    Munoz-Clares, Rosario A.
    Gonzalez-Segura, Lilian
    Diaz-Sanchez, Angel G.
    CHEMICO-BIOLOGICAL INTERACTIONS, 2011, 191 (1-3) : 137 - 146
  • [9] On the Role of Short and Strong Hydrogen Bonds on the Mechanism of Action of a Model Chymotrypsine Active Site
    Mino, German
    Contreras, Renato
    JOURNAL OF PHYSICAL CHEMISTRY A, 2009, 113 (19): : 5769 - 5772
  • [10] Short, strong hydrogen bonds at the active site of human acetylcholinesterase: Proton NMR studies
    Massiah, MA
    Viragh, C
    Reddy, PM
    Kovach, IM
    Johnson, J
    Rosenberry, TL
    Mildvan, AS
    BIOCHEMISTRY, 2001, 40 (19) : 5682 - 5690