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Experimental design of the kinetic resolution of a key precursor of high‐value bioactive myo ‐inositols by an immobilized lipase
Author(s) -
Cunha Aline G.,
da Silva Angelo A. T.,
Godoy Mateus G.,
Almeida Rodrigo V.,
Simas Alessandro B. C.,
Freire Denise M. G.
Publication year - 2013
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.3806
Subject(s) - kinetic resolution , chemistry , substrate (aquarium) , lipase , candida antarctica , acylation , enantiomeric excess , vinyl acetate , ethyl acetate , resolution (logic) , enantiomer , water activity , catalysis , organic chemistry , enzyme , stereochemistry , enantioselective synthesis , oceanography , polymer , artificial intelligence , geology , computer science , copolymer , geotechnical engineering , water content , engineering
BACKGROUND: The response surface methodology was successfully applied to the optimization of the reaction variables for the kinetic resolution of a precursor of high‐value myo ‐inositols, ( ± )‐1,2‐ O ‐isopropylidene‐3,6‐di‐ O ‐benzyl‐ myo ‐inositol (( ± )‐1), by Novozym 435. The resolutions were run separately, with two acylating agents, ethyl acetate and vinyl acetate, in a solvent‐free system. The variables analyzed were reaction temperature, substrate concentration, water concentration and enzyme activity. A statistical model was employed for the evaluation of the influence of the variables on conversion and enantiomeric excess ( ee ). RESULTS: The optimal conditions for this resolution using vinyl acetate as acylating agent were 45 °C, 5 mg mL −1 of substrate, 71 U of enzyme activity and 0%w/w of water concentration. The high conversion (49.2 %) and ee (>99%) reached in the chemoenzymatic synthesis of acylated product, L‐(−)‐5‐ O ‐Acetyl‐3,6‐di‐ O ‐benzyl‐1,2‐ O ‐isopropylidene‐ myo ‐inositol, secure the efficient synthesis of the D enantiomorph present in the original racemic mixture (( ± )‐1) as well. CONCLUSIONS: The use of the experimental design strategy was productive, leading to a 14‐fold increase in the productivity of the reaction compared with the non‐optimized conditions. Both derivative L‐(−)‐2 and remaining substrate D‐(+)‐1 were obtained at high ee . © 2012 Society of Chemical Industry