Biomimetic oxidation and asymmetric reduction with coenzyme NAD analogs

Nobuhiro Kanomata*

*この研究の対応する著者

研究成果: Article査読

6 被引用数 (Scopus)

抄録

Coenzyme NAD+/NADH, a major cofactor of dehydrogenases, functions as an autorecycling redox agent in biological systems, which is exemplified by enantioselective reduction of pyruvate to L-lactate and oxidation of glyceraldehyde-3-phosphate to 1,3-bisphosphoglycerate as is observed in anaerobic glycolysis. This article reviews biomimetic asymmetric reduction and oxidation in NAD+/NADH model systems. The first part outlines highly enantioselective reduction of benzoylformate, a lactate analog, with representative NADH model compounds mimicking biological reduction in lactate dehydrogenase. In this section, the well-developed model reactions are grouped based on the types of NADH models; one having a chiral center at the C-4 position of its 1,4-dihydronicotinoyl ring and the other good for recycling use. The latter half describes the detailed history on the less developed biomimetic oxidation with NAD+ model compounds. This section classifies the model reactions based on the types of model substrates to summarize the oxidation of alcohols, aldehydes, and formates into aldehydes (or ketones), carboxylates, and carbon dioxide, respectively, with regioselective formation of the corresponding NADH model compounds as analogous reactions in alcohol-, glyceraldehyde-3-phosphate-, and formate dehydrogenases.

本文言語English
ページ(範囲)512-522
ページ数11
ジャーナルYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
57
6
DOI
出版ステータスPublished - 1999
外部発表はい

ASJC Scopus subject areas

  • 有機化学

フィンガープリント

「Biomimetic oxidation and asymmetric reduction with coenzyme NAD analogs」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル