有机化学 ›› 2014, Vol. 34 ›› Issue (10): 2163-2171.DOI: 10.6023/cjoc201403049 上一篇    下一篇

研究简报

具胆酸单元氢化烟酰胺腺嘌呤二核苷酸模型物的合成及其仿酶不对称还原性

李大芝, 胡碧玮, 杨运旭, 杨超, 霍宝龙, 薛灵伟, 禹菲菲, 王爱志   

  1. 北京科技大学化学与生物工程学院 北京 100083
  • 收稿日期:2014-03-23 修回日期:2014-05-16 出版日期:2014-10-25 发布日期:2014-06-09
  • 通讯作者: 杨运旭 E-mail:yxyang63@aliyun.com
  • 基金资助:

    国家自然科学基金(No. 20972015)、北京市自然科学基(No. 2112026)资助项目.

Synthesis of Cholate-Based Nicotinamide Adenine Dinucleotide Hydrogen Models and Their Enzyme Mimic Asymmetric Reduction Ability

Li Dazhi, Hu Biwei, Yang Yunxu, Yang Chao, Huo Baolong, Xue Lingwei, Yu Feifei, Wang Aizhi   

  1. School of Chemistry and Biological Engineering, University of Science and Technology Beijing, Beijing 100083
  • Received:2014-03-23 Revised:2014-05-16 Online:2014-10-25 Published:2014-06-09
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 20972015) and the Natural Science Foundation of Beijing City (No. 2112026).

设计并合成了5种具有胆酸单元的氢化烟酰胺腺嘌呤二核苷酸(NADH)模型化合物,并以苯甲酰甲酸甲酯为底物,镁离子为催化剂,研究了模型化合物的不对称还原能力. 结果表明这些模型化合物能够将α-酮酸酯还原为α-羟基酸酯,有一定的负氢转移能力,但它们的手性还原能力不佳,对映体过量值最高为26%.

关键词: 胆酸, NADH, 手性还原, 苯甲酰甲酸甲酯

Five cholate-based nicotinamide adenine dinucleotide hydrogen (NADH) models have been designed and synthesized. The asymmetric reduction of methyl benzoylformate by the NADH models was investigated under the catalyst of Mg2+ as complex center. The results indicated that these NADH models could reduce α-keto ester to α-hydroxyl ester, possessing the ability of hydride transfer and the low ability of chiral reduction. The enantiomeric excess value of the reduced product was up to 26%.

Key words: cholic acid, NADH, chiral reduction, methyl benzoylformate