Reduction by a model of NAD(P)H. Effect of metal ion and stereochemistry on the reduction of .alpha.-keto esters by 1,4-dihydronicotinamide derivatives

Onishi, Yasunobu; Kagami, Masayuki; Ono, Akira

doi:10.1021/ja00849a055

Cited by 165 publications

(38 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…3 and that the (S)-alcohol would be the major product. Ohnishi, Kagami & Ohno (1975) reached the opposite conclusion by assuming that the carboxamide group is rotated 180 ° from the position shown in Fig. 3.…”

mentioning

confidence: 99%

“…Ohnishi, Kagami & Ohno (1975) 0567-7408/81/081637-04501.00 non-enzymatic reduction of pyruvate esters by a 1,4-dihydronicotinamide; a reaction which mimics that catalyzed by lactate dehydrogenase (Everse & Kaplan, 1973). The reduction was achieved by the use of the chiral dihydronicotinamides (1).…”

mentioning

confidence: 99%

“…It is important to note that the compound whose structure is reported here is the S enantiomer. The compound drawn above and discussed by Ohnishi, Kagami & Ohno (1975) is the R enantiomer.…”

mentioning

confidence: 99%

“…The structural results outlined above allow a discussion of the experiments of Ohnishi, Kagami & Ohno (1975). Since those workers used a nicotinamide with an R configuration the following discussion is in terms of that enantiomer.…”

mentioning

confidence: 99%

“…Since those workers used a nicotinamide with an R configuration the following discussion is in terms of that enantiomer. Ohnishi, Kagami & Ohno (1975) reasoned that the most favorable orientation of the substrate and the dihydropyridine (1) could be predicted if stereochemical factors are considered. A ketone oriented parallel to the dihydropyridine ring would be expected to approach the least hindered side of the molecule.…”

mentioning

confidence: 99%

See 4 more Smart Citations

Structure of (S)-N-(α-methylbenzyl)nicotinamide; a chiral NADH analog

Little¹,

Morimoto²

1981

Acta Crystallogr Sect B

View full text Add to dashboard Cite

C23H29NO 6 1637 the three planar segments in the molecule result in a rather loosely packed structure consistent with the ease of sublimation of the solid material.We wish to thank Dr Richard A. Kretchmer Least-squares refinement (nonhydrogen atoms anisotropic, H atoms isotropic) led to a final unweighted R value (on F; 1392 observed reflections) of 0.038. The carboxamide group is rotated by 34 ° from the plane of the pyridine ring and oriented such that the carbonyl O atom is directed toward the 4 position of the pyridine ring. The hybridization of the amide N is close to sp2; the chiral C atom, C(7), is 0.20A out of the plane of the carboxamide group. The phenyl group extends toward the B side of the molecule and the methyl group towards the A side. The conformation of the molecule is discussed in relation to studies of stereospecific reduction by models for the reduced pyridine nucleotide, NADH. It is found that the structure leads to predictions of asymmetric induction which are opposite to those experimentally observed. Structure of (S)-N-(~-

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations