1991 Fiscal Year Final Research Report Summary
Preparation and Reactivity of an Alcohol Dehydrogenase-NADH Model
Project/Area Number |
02670950
|
Research Category |
Grant-in-Aid for General Scientific Research (C)
|
Allocation Type | Single-year Grants |
Research Field |
Chemical pharmacy
|
Research Institution | Kanazawa Uiversity |
Principal Investigator |
SAITO Tohru Kanazawa University, Faculty of Pharmaceutical Sciences, Research Associate, 薬学部, 助手 (00110544)
|
Project Period (FY) |
1990 – 1991
|
Keywords | Alcohol dehydrogenase-NADH model / 1, 4-Dihydronicotinamide / Adenine / Magnesium ion / ^1H-NMR / UV spectrum / Methyl benzoylfoumate / Reduction |
Research Abstract |
As a model for alcohol dehydrogenase-NADH couple, a series of macrocyclic 1, 4-dihydronicotinamides 1a-c linked adenine was prepared via N-[omega-(9-(6-hydroxyhexyl) purin-6-ylamino) alkyl]nicotinamide (a, alkyl = butyl ; b, pentyl ; c, hexyl) by iodination of the hydroxyl group followed by cyclization to the pyridinium salt and reduction. The coordination behavior of 1b, c with magnesium ion in acetonitrile was investigated by ultraviolet and ^1H-NMR spectroscopies, and compared with those of 1-methyl-3-(N-methylcarbamoyl)-1, 4-dihydropyridine (2) and 1-[6-(6-methylamino-9H-purin9-yl) lhexyl-3-(N-methylcarbamoyl)-1, 4-dihydropyridine (3). The adenine moiety in 1b, c accelerates complexation of magnesium ion at the dihydronicotinamide moiety, presumably by acting as a pi electron donor. The reactivity of 1a-c, 2, and 3 toward methyl benzoylformate in the presence of magnesium perchlorate in acetonitrile was kinetically investigated and found to be of the order 1b>1a>3<greater than or equal>1c>2 under the conditions teste
|