Biomimetic Oxidation of Aldehyde with NAD+ Models: Glycolysis-Type Hydrogen Transfer in an NAD+/NADH Model System

Abstract

Just like in biological systems, the GAPDH-catalyzed oxidation of aldehyde to carboxylate proceeds in conjunction with 1,4-selective reduction of NAD to NADH model compounds [Eq. (1)]. The combination of GAPDH- and LDH-type transfer reactions is also described here as a system mimic for the NAD /NADH redox cycle in anaerobic glycolysis. GAPDH=D-glyceraldehyde-3-phosphate dehydrogenase, LDH=L-lactate dehydrogenase.

Thermodynamic Parameters of Elementary Steps for 3,5-Disubstituted 1,4-Dihydropyridines To Release Hydride Anions in Acetonitrile

“…Organic hydrides (also called as metal-free hydrides) are one of the most important organic compounds that can provide a hydride ion to the reaction partner in chemical reactions. − Because of having many special chemical properties compared with the metal hydrides (also called as inorganic hydrides, such as KH, NaH, NaBH 4 , LiAlH 4 , etc), organic hydrides have been receiving extensive applications in biomimetic chemistry, , organic synthetic chemistry, , energy chemistry, green chemistry, , materials chemistry, , and many others . Below are listed some representative examples (Scheme ).…”

Where and How Does an Organic Molecule Having a C–X Bond Release X– Anion Like an Inorganic Compound? A Theoretical Study

“…One of the important classes of organic compounds are organic hydride donor structures that can release hydride anion in the chemical and biochemical reactions. , For example, organic compounds such as NAD­(P)­H, , FADH 2 , − tetrahydrofolate, − and ascorbic acid (Vitamin C) , that naturally release hydride play important roles in the processes of biological reductions and bioantioxidations. − The main reason for the importance of these compounds is that they have many important chemical properties and quite extensive applications, such as models of some natural organic hydride donors to examine the thermodynamics, kinetics, and mechanisms of the hydride transfer; − as organic reducing agents to efficiently reduce various olefins, aldehydes, ketones, epoxy compounds, organic halides, and imides for organic synthesis; − as functional molecules to construct various molecule devices; − and as various molecular probes to explore the essence of living phenomena. − On the other hand, because the hydrogen is one of the most promising candidates for the replacement of current carbon-based energy sources, the role of these compounds as hydrogen-stored materials to release hydrogen gas is significant. − It is highly important to develop the efficient and practical methods for the hydrogenation from easy-to-handle resources.…”

Silver(I) as a widely applicable, homogeneous catalyst for aerobic oxidation of aldehydes toward carboxylic acids in water—“silver mirror”: From stoichiometric to catalytic

“…With its natural abundance and inherent greener characteristics, water has been a desirable solvent for chemists (26)(27)(28). Although biological oxidations in water using enzymes or microorganisms are well recognized (29)(30)(31)(32)(33)(34), it was only in 2000 that Sheldon established an aqueous-phase homogeneous catalytic aerobic oxidation methodology (35,36). Yet, the method still requires a precious metal (palladium), a high pressure (30 bar), and a large amount of additive (TEMPO).…”