Intramolecular charge‐transfer interaction between the oxidized and reduced forms of nicotinamide in a polymeric system. NAD coenzyme model

Shinkai, Seiji; Tamaki, Kiyoshi; Kunitake, Toyoki

doi:10.1002/bip.1976.360150514

Cited by 8 publications

(1 citation statement)

References 15 publications

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“…), probably because of the formation of polymer complexes due to the electrostatic interaction between VNic-SO2-anions and VNic cations and/or to the charge transfer interaction between reduced and oxidized forms of nicotinamides. 16 It was found that the addition of excess triethylbenzyl-ammonium chloride is effective in avoiding precipitation during dithionite reduction. 18 The reaction mixture was kept homogeneous in the presence of triethylbenzylammonium chloride (2.60 g, 1.14 X mole) and finally gave yellow precipitates.…”

Section: Vnicmentioning

confidence: 99%

Coenzyme models. 15. A polymeric model system for the NADH‐dependent dehydrogenase enzymes

Shinkai

Tanake

Ide

et al. 1979

J. Polym. Sci. Polym. Chem. Ed.

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Copolymers of 4‐vinylpyridine (4‐VP) and N‐(p‐vinylbenzyl)‐1,4‐dihydronicotinamide (VNicH) were synthesized, and a carbonyl substrate (benzil) was reduced to alcohol in an aqueous ethanol solution in the absence and presence of metal ions (Zn2+ and Ni2+) as part of a model study of NADH‐dependent enzymes. The reduction rates by VNicH in polymers were four to seven times greater than that of the corresponding monomeric analog (N‐benzyl‐1,4‐dihydronicotinamide). Added metal ions catalyzed the reduction by VNicH‐29 (VNicH content, 29 mole%) but inhibited the reduction by VNicH‐9 (VNicH content, 9 mole%). It was suggested that metal catalysis occurs only when metal ions are bound closely near the dihydronicotinamide moiety.

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Section: Vnicmentioning

confidence: 99%

Coenzyme models. 15. A polymeric model system for the NADH‐dependent dehydrogenase enzymes

Shinkai

Tanake

Ide

et al. 1979

J. Polym. Sci. Polym. Chem. Ed.

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Polymeric Matrices in Chemical Reactions — Silent or Active Partners?

Warshawsky

1979

Israel Journal of Chemistry

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Coenzyme models, 5. Addition reaction of cyanide ion to monomeric and polymeric nicotinamides. Correlation between equilibria and reaction rates

1977

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Rate and equilibrium constants ( k r and K , respectively) for the addition of cyanide ion to poly[ 1-(4-vinylbenzyl)nicotinamide chloride] (poly j 1-[4-(3-aminocarbonyIpyridiniomethyl)phenyl]ethylene chloride)) (poly(1)) and a corresponding monomeric derivative of nicotinamide, 3-aminocarbonyl-I -benzylpyridinium chloride (2), were evaluated at 30°C, in an aqueous system. The rate constant for the reaction of poly(1) with C N -at p=O,1 mol I -' was found to be higher by a factor of 22 and the association constant byafactorofabout 65,compared with thosefor thereactionof2withCN-. At a lower ionic strength (p=O,OO8 mol I-'), the reaction parameters were markedly enhanced (108-fold and 218-fold, respectively). The rate enhancements in the polymeric system are attributable to the increase in the AS*, term. This favorable entropy term caused the deviation from the linear log K-log k , relationship which holds strictly for monomeric compounds.

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Intramolecular charge‐transfer interaction between the oxidized and reduced forms of nicotinamide in a polymeric system. NAD coenzyme model

Cited by 8 publications

References 15 publications

Coenzyme models. 15. A polymeric model system for the NADH‐dependent dehydrogenase enzymes

Coenzyme models. 15. A polymeric model system for the NADH‐dependent dehydrogenase enzymes

Polymeric Matrices in Chemical Reactions — Silent or Active Partners?

Coenzyme models, 5. Addition reaction of cyanide ion to monomeric and polymeric nicotinamides. Correlation between equilibria and reaction rates

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