Mechanistic Models of Asymmetric Reductions - Tapa blanda

Sinopsis

1 Introduction.- 2 NAD(P)H as a Coenzyme.- 3 Stereochemistry in NAD(P)+-Dependent Dehydrogenases.- 3.1 Stereospecific Hydrogen Transfer from NAD(P)H.- 3.2 Stereospecificity in an Alcohol Dehydrogenase.- 3.3 Stereospecificity in Other Dehydrogenases.- 3.4 Stereochemistry of Transferring Hydrogen.- 3.5 Stereochemistry with Respect to the Substrate.- 4 Enzymatic Reductions.- 4.1 Structure of Dehydrogenase and Substrate Binding.- 4.2 Mechanism of Hydride Transfer.- 5 Asymmetric Reduction by Model Compounds of NAD(P)H.- 5.1 Model Reactions of NAD(P)H-Dependent Dehydrogenases.- 5.2 The First Asymmetric Reduction.- 5.3 The Role of Metal Ion.- 5.4 Mechanism of the Reduction with NAD(P)H Models.- 6 Stereochemical Course of the Reduction.- 6.1 Stereochemical Course in the Reduction with PNPH.- 6.2 Reduction with a Model Which Contains Chirality at the 4 Position.- 6.3 Further Comment on the Stereochemistry of PNPH and Its Analogues.- 6.4 Factors That Determine the Stereoselectivity.- 6.5 NAD(P)H Model Compound Incoroporating a Macrocycle.- 6.6 Models That Contain Two Chiral 1,4-Dihydronicotinamide Moieties.- 6.7 Asymmetric Reduction of Nonactivated Substrate.- 7 Asymmetric Reduction in a Chiral Reaction Field.- 8 Polar Effect Exerted by Other Asymmetric Reactions.- 8.1 Reduction to Afford Diastereoisomers.- 9 Diastereo-Differentiation at the 4 Position of 1,4-Dihydropyridine.- 9.1 Explanation of A- or B-Specificity in Dehydrogenases.- 9.2 Self-Immolative Transfer of Chirality Between NAD(P)+ and NAD(P)H Models: a Chirality Sink.- 9.3 Diastereo-Differentiation for Prochiral Hydrogens at the 4 Position.- 10 Stereochemistry of Flavin-Dependent Reactions.- 10.1 Flavin as a Coenzyme.- 10.2 Stereochemistry of Flavin-Dependent Enzymatic Reactions.- 10.3 Model Reaction of Asymmetric Inter-Coenzyme Hydrogen Transfer.- 10.4 Asymmetric Reduction by a Model of Flavin Coenzyme.- 11 Asymmetric Synthesis of ?-Amino Acids.- 12 Recent Progress in Asymmetric Reactions Mediated by an Enzyme.- 13 References.

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