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Biocatalytic synthesis of C 3 chiral building blocks by chloroperoxidase‐catalyzed enantioselective halo‐hydroxylation and epoxidation in the presence of ionic liquids
Author(s) -
Liu Yan,
Wang Yali,
Jiang Yucheng,
Hu Mancheng,
Li Shuni,
Zhai Quanguo
Publication year - 2015
Publication title -
biotechnology progress
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.572
H-Index - 129
eISSN - 1520-6033
pISSN - 8756-7938
DOI - 10.1002/btpr.2076
Subject(s) - enantioselective synthesis , chemistry , glycidol , ionic liquid , hydroxylation , catalysis , organic chemistry , chemoselectivity , solubility , combinatorial chemistry , organic synthesis , yield (engineering) , enzyme , materials science , metallurgy
The optically active C3 synthetic blocks are remarkably versatile intermediates for the synthesis of numerous pharmaceuticals and agrochemicals. This work provides a simple and efficient enzymatic synthetic route for the environment‐friendly synthesis of C3 chiral building blocks. Chloroperoxidase (CPO)‐catalyzed enantioselective halo‐hydroxylation and epoxidation of chloropropene and allyl alcohol was employed to prepare C3 chiral building blocks in this work, including ( R )‐2,3‐dichloro‐1‐propanol (DCP*), ( R )‐2,3‐epoxy‐1‐propanol (GLD*), and ( R )‐3‐chloro‐1‐2‐propanediol (CPD*). The ee values of the formed C3 chiral building blocks DCP*, CPD*, and glycidol were 98.1, 97.5, and 96.7%, respectively. Moreover, the use of small amount of imidazolium ionic liquid enhanced the yield efficiently due to the increase of solubility of hydrophobic organic substrates in aqueous reaction media, as well as the improvement of affinity and selectivity of CPO to substrate. © 2015 American Institute of Chemical Engineers Biotechnol. Prog ., 31:724–729, 2015