当前位置: X-MOL 学术Appl. Catal. A Gen. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Chemoenzymatic synthesis of (S)-Pindolol using lipases
Applied Catalysis A: General ( IF 5.5 ) Pub Date : 2017-08-04 , DOI: 10.1016/j.apcata.2017.08.003
Gledson Vieira Lima , Marcos Reinaldo da Silva , Thiago de Sousa Fonseca , Leandro Bezerra de Lima , Maria da Conceição Ferreira de Oliveira , Telma Leda Gomes de Lemos , Davila Zampieri , Jose Cleiton Sousa dos Santos , Nathalia Saraiva Rios , Luciana Rocha Barros Gonçalves , Francesco Molinari , Marcos Carlos de Mattos

A straightforward chemoenzymatic synthesis of (S)-Pindolol has been developed. The key step involved the enzymatic kinetic resolution of rac-2-acetoxy-1-(1H-indol-4-yloxy)-3-chloropropane with lipase from Pseudomonas fluorescens via hydrolytic process to obtain enantiomerically enriched halohydrin (2S)-1-(1H-indol-4-yloxy)-3-chloro-2-propanol (96% ee) and (2R)-2-acetoxy-1-(1H-indol-4-yloxy)-3-chloropropane (97% ee). The latter was subjected to a hydrolysis reaction catalyzed by Candida rugosa leading to (2R)-1-(1H-indol-4-yloxy)-3-chloro-2-propanol (97% ee), followed by a reaction with isopropylamine, producing (S)-Pindolol (97% ee) in quantitative yield.



中文翻译:

使用脂肪酶化学酶促合成(S)-哌多洛尔

已经开发了一种简单的化学酶法合成(S)-吲哚洛尔的方法。关键步骤涉及通过荧光水解过程,从荧光假单胞菌中用脂肪酶对rac -2-乙酰氧基-1-(1 H-吲哚-4-基氧基)-3-氯丙烷进行酶促动力学拆分,得到对映体富集的卤代醇 2 S)-1 -(1 H-吲哚-4-基氧基)-3-氯-2-丙醇(96%ee)和(2 R)-2-乙酰氧基-1-(1 H-吲哚-4-基氧基)-3-氯丙烷(97%ee)。后者经历了由假丝酵母Candida rugosa)催化的水解反应,从而导致2 R)-1-(1 H-吲哚-4-基氧基)-3-氯-2-丙醇(97%ee),然后与异丙胺反应,定量生成(S)-吲哚洛尔(97%ee)屈服。

更新日期:2017-08-04
down
wechat
bug