Coupling chiral homogeneous biocatalytic reactions with benign heterogeneous separation

Elizabeth M. Hill, James M. Broering, Jason P. Hallett, Andreas S. Bommarius, Charles L. Liotta, Charles A. Eckert

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

We describe a method for sustainable biocatalysis in an organic aqueous tunable solvent (OATS) system in which a hydrophobic substrate is transformed with a homogeneous enzymatic catalyst in a single liquid phase. Subsequent CO2 addition produces a biphasic mixture where the hydrophobic product partitions preferentially into the organic rich phase for separation while the hydrophilic enzyme catalyst partitions into the aqueous rich phase, where it is recyclable. Greater than 99% enantiomeric excess (ee) is shown for catalyzed hydrolysis of rac-1-phenylethyl acetate with Candida antarctica lipase B (CAL B) both before and after CO2-induced separation. Additionally, processing parameters in OATS systems are discussed. This system combines homogeneous enzymatic reactions with a built-in heterogeneous separation for enantiomerically pure products.

Original languageEnglish (US)
Pages (from-to)888-893
Number of pages6
JournalGreen Chemistry
Volume9
Issue number8
DOIs
StatePublished - Jan 1 2007

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catalyst
Catalysts
Candida
Lipases
hydrolysis
Hydrolysis
acetate
Acetates
Enzymes
enzyme
substrate
liquid
Liquids
Substrates
Processing
product
Biocatalysis
Antarctica
method
parameter

Cite this

Hill, E. M., Broering, J. M., Hallett, J. P., Bommarius, A. S., Liotta, C. L., & Eckert, C. A. (2007). Coupling chiral homogeneous biocatalytic reactions with benign heterogeneous separation. Green Chemistry, 9(8), 888-893. https://doi.org/10.1039/b701409k

Coupling chiral homogeneous biocatalytic reactions with benign heterogeneous separation. / Hill, Elizabeth M.; Broering, James M.; Hallett, Jason P.; Bommarius, Andreas S.; Liotta, Charles L.; Eckert, Charles A.

In: Green Chemistry, Vol. 9, No. 8, 01.01.2007, p. 888-893.

Research output: Contribution to journalArticle

Hill, EM, Broering, JM, Hallett, JP, Bommarius, AS, Liotta, CL & Eckert, CA 2007, 'Coupling chiral homogeneous biocatalytic reactions with benign heterogeneous separation', Green Chemistry, vol. 9, no. 8, pp. 888-893. https://doi.org/10.1039/b701409k
Hill EM, Broering JM, Hallett JP, Bommarius AS, Liotta CL, Eckert CA. Coupling chiral homogeneous biocatalytic reactions with benign heterogeneous separation. Green Chemistry. 2007 Jan 1;9(8):888-893. https://doi.org/10.1039/b701409k
Hill, Elizabeth M. ; Broering, James M. ; Hallett, Jason P. ; Bommarius, Andreas S. ; Liotta, Charles L. ; Eckert, Charles A. / Coupling chiral homogeneous biocatalytic reactions with benign heterogeneous separation. In: Green Chemistry. 2007 ; Vol. 9, No. 8. pp. 888-893.
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