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
  • [31] Driving the Active Site Incorporation in Zeolitic Materials via the Organic Structure-Directing Agent Through Development of H-Bonds with Hydroxyl Groups
    Bernardo-Maestro, Beatriz
    Li, Jian
    Perez-Pariente, Joaquin
    Lopez-Arbeloa, Fernando
    Gomez-Hortiguela, Luis
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (42)
  • [32] Neighbouring group participation of thiol through aldehyde group assisted thiolysis of active ether: ratiometric and vapor phase fast detection of hydrogen sulfide in mixed aqueous media
    Das, Avijit Kumar
    Goswami, Shyamaprosad
    Quah, Ching Kheng
    Fun, Hoong-Kun
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (07) : 5669 - 5675
  • [33] Diiron dithiolate complexes containing intra-ligand NH ••• S hydrogen bonds:: [FeFe] hydrogenase active site models for the electrochemical proton reduction of HOAc with low overpotential
    Yu, Ze
    Wang, Mei
    Li, Ping
    Dong, Weibing
    Wang, Fujun
    Sun, Licheng
    DALTON TRANSACTIONS, 2008, (18) : 2400 - 2406
  • [34] The enhancement of photocatalytic hydrogen evolution in imine-linked pyrene-based covalent organic frameworks through the regulation of active site distances
    Zong, Jiawen
    Liu, Huanyu
    Lian, Wei
    Dai, Lu
    Li, Pengfei
    JOURNAL OF MATERIALS CHEMISTRY A, 2025, 13 (08) : 6095 - 6101
  • [35] Presence of 18-A long hydrogen bond track in the active site of Escherichia coli DNA polymerase I (Klenow fragment) -: Its requirement in the stabilization of enzyme-template-primer complex
    Singh, K
    Modak, MJ
    JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (13) : 11289 - 11302
  • [36] Role of the invariant peptide fragment forming NH•••S hydrogen bonds in the active site of cytochrome P-450 and chloroperoxidase:: Synthesis and properties of Cys-containing peptide Fe(III) and Ga(III) (octaethylporphinato) complexes as models
    Ueno, T
    Nishikawa, N
    Moriyama, S
    Adachi, S
    Lee, K
    Okamura, T
    Ueyama, N
    Nakamura, A
    INORGANIC CHEMISTRY, 1999, 38 (06) : 1199 - 1210
  • [37] TRANSITION-METAL COMPLEXES WITH SULFUR LIGANDS .48. NITROGENASE MODEL COMPOUNDS - [MU-N2H2(FE(NHS4))2], THE PROTOTYPE FOR THE COORDINATION OF DIAZENE TO IRON SULFUR CENTERS AND ITS STABILIZATION THROUGH STRONG N-H...S HYDROGEN-BONDS
    SELLMANN, D
    SOGLOWEK, W
    KNOCH, F
    MOLL, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (09): : 1271 - 1272