Chemoenzymatic Synthesis of an Enantiomerically Enriched Bicyclic Carbocycle Using <i>Candida parapsilosis</i>ATCC 7330 Mediated Enantioselective Hydrolysis  

作　　者：Thangavelu Saravanan Anju Chadha Tarur Konikkaledom Dinesh Namasivayam Palani Sengottuvelan Balasubramanian 

机构地区：[1]Laboratory of Bioorganic Chemistry, Department of Biotechnology, Indian Institute of Technology Madras, Chennai, India [2]National Center for Catalysis Research, Indian Institute of Technology Madras, Chennai, India [3]Department of Inorganic Chemistry, University of Madras, Guindy Campus, Chennai, India [4]ITC Life Sciences and Technology Centre, ITC Limited, Peenya Industrial Area, Phase I, Bangalore, India

出　　处：《International Journal of Organic Chemistry》2015年第4期271-281,共11页有机化学国际期刊（英文）

摘　　要：Enantiomerically enriched (R)-1-(2-bromocycloalkenyl)-3-buten-1-ol and its derivatives were obtained via enantioselective hydrolysis [resolution] with good enantioselectivities (E = 31 to >500) using Candida parapsilosis ATCC 7330. The various reaction parameters were optimized for enantioselective hydrolysis to achieve high enantiomeric excess (ee) and conversions. Among the substrates tested, (RS)-1-(2-bromocyclohex-1-en-1-yl) but-3-yn-1-yl acetate was hydrolysed by the biocatalyst in 12 h to the corresponding (R)-alcohol in 49% conversion and >99 ee. The optically pure allylic alcohol thus obtained was used as a chiral starting material for the synthesis of an enantiomerically enriched bicyclic alcohol effectively establishing achemoenzymatic route.Enantiomerically enriched (R)-1-(2-bromocycloalkenyl)-3-buten-1-ol and its derivatives were obtained via enantioselective hydrolysis [resolution] with good enantioselectivities (E = 31 to >500) using Candida parapsilosis ATCC 7330. The various reaction parameters were optimized for enantioselective hydrolysis to achieve high enantiomeric excess (ee) and conversions. Among the substrates tested, (RS)-1-(2-bromocyclohex-1-en-1-yl) but-3-yn-1-yl acetate was hydrolysed by the biocatalyst in 12 h to the corresponding (R)-alcohol in 49% conversion and >99 ee. The optically pure allylic alcohol thus obtained was used as a chiral starting material for the synthesis of an enantiomerically enriched bicyclic alcohol effectively establishing achemoenzymatic route.

关 键 词：CHEMOENZYMATIC Synthesis Enantioselective Hydrolysis Candida parapsilosis ATCC 7330 HYDROLASES BICYCLIC Carbocycle 

分 类 号：O6[理学—化学]