1982
DOI: 10.1073/pnas.79.15.4604
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Concerning 1e- transfer in reduction by dihydronicotinamide: reaction of oxidized flavin and flavin radical with N-benzyl-1,5-dihydronicotinamide.

Abstract: The rates of reaction of 5-ethyl-3-methyllumiflavinium perchlorate and.5-ethyl-3-methyllumiflavinyl radical with a NADH analogue, N-benzyl-1,4-dihydronicotinamide, were measured anaerobically in tert-butanol and .5% acetonitrile/ 95% tert-butanol-solutions at 30C. The biphasic kinetics observed for the reaction of flavin radical with dihydronicotinamide were interpreted in terms.of both a leC and a 2e-mechanism; the former was found to be inadequate based on experimental requirements of the mechanism. The dihy… Show more

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Cited by 18 publications
(10 citation statements)
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“…Indeed, when hamster kidney membranes were prepared in the absence of detergent, MT 3 loosely associated with membrane components and fractionated almost equally in the pellet and in the supernatant of an ultracentrifugation. 3 This is consistent with the elution from the DEAE column at low ionic strength (30 -40 mM NaCl), and with the previously described hydrophobic properties of QR 2 (9,14,20,25). Third, the present QR 2 transfected (1-4) CHO cells.…”
Section: Discussionsupporting
confidence: 88%
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“…Indeed, when hamster kidney membranes were prepared in the absence of detergent, MT 3 loosely associated with membrane components and fractionated almost equally in the pellet and in the supernatant of an ultracentrifugation. 3 This is consistent with the elution from the DEAE column at low ionic strength (30 -40 mM NaCl), and with the previously described hydrophobic properties of QR 2 (9,14,20,25). Third, the present QR 2 transfected (1-4) CHO cells.…”
Section: Discussionsupporting
confidence: 88%
“…This hamster/ human difference was also observed with the enzymatic data, where IC 50 were 1.5-20-fold higher with human QR 2 compared with hamster MT 3 /QR 2 . Besides, hamster MT 3 /QR 2 and human QR 2 had a similar Michaelis affinity for menadione and BNAH, with a K m of about 60 M for BNAH, comparable with the K m of NAD(P)H for QR 1 (20,23). Dicoumarol was confirmed as a poor inhibitor of QR 2 , with an IC 50 of about 600 M. Interestingly, the MT 3 compounds proved to be relatively good inhibitors of the enzyme, especially of the hamster preparation where the IC 50 of iodomelatonin and S26553 were in the micromolar range, well below the K m of the substrates.…”
Section: Terminology and Assays Of Mtmentioning
confidence: 73%
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“…Flavin reduction by NCBs such as BNAH is known to occur through direct hydride transfer in solution. 48,49 Different substituents were previously shown to affect the overall NCB redox potential and lead to different FAD reduction rates. 31 Therefore, we screened six NCBs bearing substituents varying from amide, acetyl, carboxylic acid to nitrile, with either a benzyl, butyl or alkyl amide chain on the nitrogen, and the classical Hantzsch ester (HEH, Figure 3E and 4), as a hydride donor for the reduction of FAD without interfering with the epoxidation.…”
Section: Styamentioning
confidence: 99%
“…As the oxidation mechanisms for the oxidation of an NADH model and thiols by flavin are well established, they are pertinent for the kinetic study. The former proceeds via a hydride transfer to the N(5) position of an isoalloxazine ring (41,42,48), and the latter proceeds via nucleophilic attack of thiolate at the C(4a) position to form an adduct, followed by attack of the second thiolate at the sulfur atom of the adduct to give the corresponding disulfide and reduced flavin (25,26) as shown in Scheme 2.…”
Section: Effect Of Hydrogen Bonding On the Oxidation Activity Of Flavinmentioning
confidence: 99%