The first protection-free synthesis of magnetic bifunctional L-proline as a highly active and versatile artificial enzyme: Synthesis of imidazole derivatives

JOURNAL OF COLLOID AND INTERFACE SCIENCE

卷:511

Article

Aghahosseini, Hamideh¹  Ramazani, Ali¹  Slepokura, Katarzyna²  Lis, Tadeusz² 

[1] Univ Zanjan, Dept Chem, POB 45195-313, Zanjan, Iran

[2] Univ Wroclaw, Fac Chem, 14 Joliot Curie St, PL-50383 Wroclaw, Poland

关键词: Bioorganic chemistry;    Protection-free synthesis;    Magnetic bifunctional L-proline;    Artificial enzyme;    Imidazole derivatives;   

DOI  :  10.1016/j.jcis.2017.10.020

来源: Elsevier

【 摘 要 】

I.-Praline is a bifunctional versatile organocatalyst that could promote a variety of useful transformations. Some passive and dynamic interactions between this simple amino acid and different substrates, which are necessary to enzymatic reactions, have given it the simplest enzyme title. Herein we presented the first report on the synthesis of magnetic bifunctional L-proline as an artificial enzyme without requiring any protection/deprotection steps according to an operationally simple process. This magnetic nano-biocatalyst is a promising catalyst that in a case study was successfully applied for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles in the 70-99% and 60-90% yields respectively, which it could be extended to the variety of L-proline-based organic transformations. The synergic effect of bifunctional L-proline shell as catalytic active site and magnetite nanoparticles core, which could function as protein mimics endow it high efficiency, versatility, recoverability, reusability and good turnover frequency, which are necessary characters for artificial enzymes' designing. (C) 2017 Elsevier Inc. All rights reserved.

【 授权许可】

Free