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

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 75期

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

页码：14175 / 14178

页数：4

共 37 条

[21] Electrostatic Fields near the Active Site of Human Aldose Reductase: 2. New Inhibitors and Complications Caused by Hydrogen Bonds
Xu, Lin
Cohen, Aina E.
Boxer, Steven G.
BIOCHEMISTRY, 2011, 50 (39) : 8311 - 8322
[22] Effects of serpin binding on the target proteinase: Global stabilization, localized increased structural flexibility, and conserved hydrogen bonding at the active site
Kaslik, G
Kardos, J
Szabo, E
Szilagyi, L
Zavodszky, P
Westler, WM
Markley, JL
Graf, L
BIOCHEMISTRY, 1997, 36 (18) : 5455 - 5464
[23] Imidazolium silanethiolates relevant to the active site of cysteine proteases. A cooperative effect in a chain of NH+•••S- hydrogen bonds
Baranowska, Katarzyna
Piwowarska, Natalia
Herman, Aleksander
Dolega, Anna
NEW JOURNAL OF CHEMISTRY, 2012, 36 (08) : 1574 - 1582
[24] Proton relay system in the active site of maltodextrinphosphorylase via hydrogen bonds with large proton polarizability: an FT-IR difference spectroscopy study
F. Bartl
Dieter Palm
Reinhard Schinzel
Georg Zundel
European Biophysics Journal, 1999, 28 : 200 - 207
[25] Proton relay system in the active site of maltodextrinphosphorylase via hydrogen bonds with large proton polarizability: an FT-IR difference spectroscopy study
Bartl, F
Palm, D
Schinzel, R
Zundel, G
EUROPEAN BIOPHYSICS JOURNAL WITH BIOPHYSICS LETTERS, 1999, 28 (03): : 200 - 207
[26] Electrosynthesis of Hydrogen Peroxide through Selective Oxygen Reduction: A Carbon Innovation from Active Site Engineering to Device Design
Zhang, Qingran
Chen, Yinguang
Pan, Jian
Daiyan, Rahman
Lovell, Emma C.
Yun, Jimmy
Amal, Rose
Lu, Xunyu
SMALL, 2023, 19 (40)
[27] Charge Relay Without Proton Transfer: Coupling of Two Short Hydrogen Bonds via Imidazole in Models of Catalytic Triad of Serine Protease Active Site
Tupikina, Elena Yu.
Sigalov, Mark V.
Alkhuder, Omar
Tolstoy, Peter M.
CHEMPHYSCHEM, 2024, 25 (12)
[28] FTIR studies of metal ligands, networks of hydrogen bonds, and water molecules near the active site Mn4CaO5 cluster in Photosystem II
Debus, Richard J.
BIOCHIMICA ET BIOPHYSICA ACTA-BIOENERGETICS, 2015, 1847 (01): : 19 - 34
[29] Positive Electronic Nickel Active Site Enhances N-H/C-H Bonds Breaking for Electrooxidation of Amines to Nitriles Coupling with Hydrogen Production
Pan, Xun
Sun, Lingzhi
Zhou, Zhaoyu
Xie, Yanan
Zheng, Jingui
Xu, Shaohan
Sun, Jie
Zeng, Jianrong
Zhao, Guohua
ADVANCED ENERGY MATERIALS, 2024, 14 (23)
[30] Hydrogen bonds involved in binding the Qi-site semiquinone in the bc1 complex, identified through deuterium exchange using pulsed EPR
Dikanov, SA
Samoilova, RI
Kolling, DRJ
Holland, JT
Crofts, AR
JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (16) : 15814 - 15823

← 1 2 3 4 →