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


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.

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Saravanan, T. , Chadha, A. , Dinesh, T. , Palani, N. and Balasubramanian, S. (2015) Chemoenzymatic Synthesis of an Enantiomerically Enriched Bicyclic Carbocycle Using Candida parapsilosis ATCC 7330 Mediated Enantioselective Hydrolysis. International Journal of Organic Chemistry, 5, 271-281. doi: 10.4236/ijoc.2015.54027.

Conflicts of Interest

The authors declare no conflicts of interest.


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