Synlett 2017; 28(04): 402-414
DOI: 10.1055/s-0036-1588665
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© Georg Thieme Verlag Stuttgart · New York

Progress on Chiral NAD(P)H Model Compounds

Cui-Bing Bai
a   Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. of China
,
Nai-Xing Wang*
a   Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. of China
,
Yalan Xing*
b   Department of Chemistry, William Paterson University of New Jersey, 300 Pompton Road, Wayne, New Jersey 07470, USA   Email: nxwang@mail.ipc.ac.cn   Email: xingy@wpunj.edu
,
Xing-Wang Lan
a   Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 01 October 2016

Accepted after revision: 09 November 2016

Publication Date:
12 December 2016 (online)


Abstract

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.

1 Introduction

2 NAD(P)H Models with Symmetric Structure

2.1 Chiral NAD(P)H Models with C 1 Symmetry

2.2 Chiral NAD(P)H Models with C 2 Symmetry

2.3 Chiral NAD(P)H Models with C 3 Symmetry

3 Symmetric Reduction

3.1 Effect of the Substituents of Dihydronicotinamide

3.2 Effect of the C-4 Substituent of Dihydropyridine

3.3 Special Structures

3.4 Applying Dehydrogenase to Biocatalytic Asymmetric Reductions with NADPH

4 Fluorescence Properties

5 Conclusion