Highly reactive and stereospecific reaction of quinoline-type NADH model compounds with methyl benzoylformate

Mikata, Yuji; Hayashi, Kayo; Mizukami, Kiyoko; Matsumoto, Shimpei; Yano, Shigenobu; Yamazaki, Norimasa; Ohno, Atsuyoshi

doi:10.1016/s0040-4039(99)02227-3

Cited by 29 publications

(18 citation statements)

References 11 publications

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“…The optical resolution and determination of the absolute configuration of each enantiomer of 1 and 2 have already been reported. 10 The CD spectra of 1 (Fig. S1 †) further support the assignment.…”

Section: Optical Resolution and CD Spectra Ofsupporting

confidence: 57%

“…The enantiomers of 3 had remained unresolved under any HPLC conditions in which (4R)-2 and (4S)-2 are completely resolved. 10 However, the recently developed HPLC column, Daicel CHIRALPAK IA, made it possible to separate the enantiomers of 3 as well as those of 2 (eluent: hexane-iPrOH-diethylamine = 95 : 5 : 0.1). Fig.…”

Section: Methodsmentioning

confidence: 99%

“…The asymmetric reduction of activated ketones or olefins with chiral NADH model compounds has been studied extensively. [1][2][3][4][5][6][7][8][9][10][11] This biomimetic molecular transformation including the nonasymmetric version of the reaction with various substrates, 12-17 has attracted considerable interest in relation to transition metal-free organic catalysts. [18][19][20] On the other hand, the reverse reactions, namely reductions of NAD model compounds exhibiting faceselective reduction, have been reported in a limited number.…”

Section: Introductionmentioning

confidence: 99%

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Consideration of molecular arrangements in regio- and enantioselective reduction of an NAD model compound controlled by carbonyl oxygen orientation

et al. 2007

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The regio- and enantioselectivity of the reduction of an NAD model compound having axial chirality with respect to the C(3)(quinolinium)-C(carbonyl) bond, 3-piperidinylcarbonyl-1,2,4-trimethylquinolinium ion (1), by using several reducing agents is described. Reaction of 1 with sodium hydrosulfite affords the 1,4-reduced product, 3-piperidinylcarbonyl-1,2,4-trimethyl-1,4-dihydroquinoline (), with low enantioselectivity, whereas sodium borohydride promotes 1,2-reduction, affording 3-piperidinylcarbonyl-1,2,4-trimethyl-1,2-dihydroquinoline () as the sole product in a moderate enantioselectivity. When 1 was reduced by the chiral NADH model compound, 2,4-dimethyl-3-(N-alpha-methylbenzylcarbamoyl)-1-propyl-1,4-dihydropyridine (Me(2)PNPH (4)), the regioselectivity and enantioselectivity of the reaction were significantly altered by the stereochemistry of 1 and 4. An achiral NADH model compound, 1-propyl-1,4-dihydronicotinamide (PNAH (5)) exhibited both high regio- and enantioselectivities. The product selectivity reflects the change in molecular arrangement in the transition state of the reaction and reveals the relative importance of the parameters governing the molecular arrangement in the reaction.

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Section: Optical Resolution and CD Spectra Ofsupporting

confidence: 57%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Consideration of molecular arrangements in regio- and enantioselective reduction of an NAD model compound controlled by carbonyl oxygen orientation

et al. 2007

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“…Mikata et al reported quinoline-type chiral NAD(P)H models 24 and 25. 50,51 A methyl group replaced one of the H atoms at C-4 of the dihydronicotinoyl structure of the models (Figure 13). The results show that these model com-pounds led to good stereoselectivity in the reaction.…”

Section: Figure 12 Nad(p)h Model 22mentioning

confidence: 99%

Progress on Chiral NAD(P)H Model Compounds

Chen

Wang

Xing

et al. 2016

Synlett

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NAD(P)H and NAD + have a significant role in biochemistry, and many NAD(P)H models received particular attention. Research in NADH models mainly focuses on asymmetric reduction and life sciences. Over the past few decades, a particularly large number of new chiral NAD(P)H models have appeared, and there have been significant developments in this area. We summarized advanced research in chiral NAD(P)H models in this paper. These models not only show very good performance in asymmetric reduction, but also have excellent fluorescence features. In addition, we present a discussion about some recent studies on the asymmetric reduction of NAD(P)H-dependent dehydrogenase, and we open a new door on research into NAD(P)H models. At last, some advances focused on the fluorescence phenomenon of some chiral NAD(P)H models have also been summarized.

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“…Quaternary salts of azaaromatics are the subject of many reports because of their interesting possibile applications, e.g. they may be used in non-linear optics (Struganova, 2000;Burtman et al, 2000), in the construction of electronic devices (Gittins et al, 2000;Bryce et al, 2001), as photochromic (Sotomayor et al, 2000) and electrochromic (Cummins et al, 2000) materials, as chemosensors (Goodall & Williams, 2000;Maidwell et al, 2000), laser dyes (Nishigaki & Nakamura, 2001;Gawinecki & Trzebiatowska, 2001) and NAD model systems (Zhu et al, 2001;Mikata et al, 2000). Some of these salts are biologically active (Goda & Saito, 2000), and also show anticancer properties (Nakanishi & Suzuki, 2001;Palm et al, 2000).…”

Section: Commentmentioning

confidence: 99%