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有机化学.pdfVIP

DOI: 10.6023/cjoc201403049 研究简报 有机化学 Chinese Journal of Organic Chemistry NOTE 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 (北京科技大学化学与生物工程学院 北京 100083) 摘要 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 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 (School of Chemistry and Biological Engineering, University of Science and Technology Beijing, Beijing 100083) Abstract Five cholate-based nicotinamide adenine dinucleotide hydrogen (NADH) models have been designed and synthe- sized. 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%. Keywords cholic acid; NADH; chiral reduction; methyl benzoylformate 辅酶烟酰胺腺嘌呤二核苷酸( 磷酸)[nicotinamide 前较多的方法是将连接一个或者多个手性中心的基团 adenine dinucleotide (phosphate) hydrogen, NAD ＋ / 接入活性基团 1,4-二氢