2018
DOI: 10.1021/acs.jpcb.8b03453
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New Insight into the Mechanism of NADH Model Oxidation by Metal Ions in Nonalkaline Media

Abstract: For a long time, it has been controversial that the three-step (e-H-e) or two-step (e-H) mechanism was used for the oxidation of nicotinamide adenine dinucleotide coenzyme (NADH) and its models by metal ions in nonalkaline media. The latter mechanism has been accepted by the majority of researchers. In this work, 1-benzyl-1,4-dihydronicotinamide (BNAH) and 1-phenyl-l,4-dihydronicotinamide are used as NADH models and ferrocenium (Fc) metal ion as an electron acceptor. The kinetics for oxidation of the NADH mode… Show more

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Cited by 19 publications
(8 citation statements)
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“…Given that the active center of the NADH coenzyme was identified as the 1,4-dihydropyridine structure, 20 chemists designed and synthesized a series of NADH models with the typical 1,4-dihydropyridine molecular skeleton, denoted as DH 2 here, to probe the reduction properties of NADH in vitro. [21][22][23] There are many reports in the literature on the use of DH 2 as efficient reducers to hydrogenate epoxides and alkenes. 58,59 In 2010, Zhu designed 42 typical 1,4-dihydropyridines with various substituents in the 3-and 5-positions and 1-position (Scheme 8), and determined the related 6 thermodynamic driving forces to construct 42 corres- The units of enthalpy changes and potentials are kcal mol −1 and V vs. Fc, respectively.…”
Section: Thermodynamics Of Organic Hydrides and Discussionmentioning
confidence: 99%
See 1 more Smart Citation
“…Given that the active center of the NADH coenzyme was identified as the 1,4-dihydropyridine structure, 20 chemists designed and synthesized a series of NADH models with the typical 1,4-dihydropyridine molecular skeleton, denoted as DH 2 here, to probe the reduction properties of NADH in vitro. [21][22][23] There are many reports in the literature on the use of DH 2 as efficient reducers to hydrogenate epoxides and alkenes. 58,59 In 2010, Zhu designed 42 typical 1,4-dihydropyridines with various substituents in the 3-and 5-positions and 1-position (Scheme 8), and determined the related 6 thermodynamic driving forces to construct 42 corres- The units of enthalpy changes and potentials are kcal mol −1 and V vs. Fc, respectively.…”
Section: Thermodynamics Of Organic Hydrides and Discussionmentioning
confidence: 99%
“…17,18 Owing to the access of this large amount of data in the literatures, Luo collected 4300 determined BDE data over 3700 organic compounds and published the Handbook of Chemical Bond Energy in 2005. 19 In the case of the NADH coenzyme, given that the core active site is the 1,4-dihydropyridine structure, 20 which is stable and easily synthesized, many 1,4-dihydropyridine compounds were synthesized and used as NADH models to investigate the redox properties in vitro, such as 1-benzyl-1,4-dihydronicotinamide (BNAH), 21 Hantzsch ester (HEH 2 ), 22 and N-methyl-9,10-dihydroacridine (AcrH 2 ). 23 Inspired by the excellent reduction ability of the NADH coenzyme in vivo, 1,4-dihydropyridine compounds, especially HEH 2 , are used as reducers to hydrogenate unsaturated compounds, such as alkenes, alkynes, aldehyde and imine.…”
Section: Guang-bin Shenmentioning
confidence: 99%
“…Nicotinamide coenzyme (NADH) 1–3 and F420 coenzyme 4–7 are the two extremely important natural redox cofactors, which exist extensively in vivo as effective hydride and electron sources taking part in a wide range of biochemical processes. They have similar functions and structures but perform unique functions, respectively.…”
Section: Introductionmentioning
confidence: 99%
“…Of the five possible isomers, only 1,2 and 1,4-DHP have been studied in depth [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 ]. Among them, 1,4-DHP is closest to NAD(P)H coenzyme; its biological applications are particularly extensive [ 17 ]. The active center of many drugs, such as nifedipine and amlodipine, is 1,4-DHP.…”
Section: Introductionmentioning
confidence: 99%