Enzyme catalysis in carbon dioxide fluids

Chemistry of hydrocarbon compounds – Compound or reaction product mixture

Reexamination Certificate

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C435S041000, C435S183000, C560S217000

Reexamination Certificate

active

06211422

ABSTRACT:

FIELD OF THE INVENTION
The present invention concerns enzyme catalysis in carbon dioxide fluids, particularly liquid or supercritical carbon dioxide fluids.
BACKGROUND OF THE INVENTION
Carbon dioxide provides an environmentally friendly solvent system for many reactions. For example, U.S. Pat. No. 5,739,223 to DeSimone describes methods of making fluoropolymers in carbon dioxide systems, U.S. Pat. No. 5,618,894 to DeSimone et al. describes nonaqueous polymerizations of fluoromonomers in carbon dioxide systems, and U.S. Pat. No. 5,679,737 to DeSimone et al. describes heterogeneous polymerizations in carbon dioxide systems.
Unfortunately, carbon dioxide has not provided a useful solvent system for enzyme catalysis. The pH of liquid or supercritical carbon dioxide is typically in the range of 4 to 5, which denatures most proteins or peptides. Hence, it would be extremely desirable to have a means for carrying out enzyme catalysis in liquid or supercritical carbon dioxide.
SUMMARY OF THE INVENTION
In view of the foregoing, a first aspect of the present invention is a method for the enzymatic production of a desired product in a liquid or supercritical carbon dioxide fluid. The method comprises: (a) providing a reaction mixture comprising at least one reaction substrate and a crosslinked enzyme crystal catalyst in a liquid or supercritical carbon dioxide fluid; and (b) reacting said substrate with said crosslinked enzyme crystal catalyst in said carbon dioxide fluid to produce said product. The reacting step is typically followed by the step of (c) separating the product from said reaction mixture.
A second aspect of the present invention is a mixture useful for the enzymatic production of a desired product in carbon dioxide fluid, said mixture comprising:
(a) at least one reaction substrate;
(b) a crosslinked enzyme crystal catalyst (that catalyzes the production of a desired product from said reaction substrate);
(c) liquid or supercritical carbon dioxide fluid; and
(d) optionally, a cosolvent.
A third aspect of the present invention is a mixture comprising the product of the foregoing method, the mixture comprising:
(a) at least one reaction product;
(b) a crosslinked enzyme crystal catalyst (that catalyzes the production of said product from a corresponding reaction substrate);
(c) liquid or supercritical carbon dioxide fluid; and
(d) optionally, a cosolvent.
The foregoing and other objects and aspects of the invention are described in greater detail in the drawings herein and the specification set forth below.


REFERENCES:
patent: 5618710 (1997-04-01), Navia et al.
patent: 5618894 (1997-04-01), DeSimone et al.
patent: 5679737 (1997-10-01), DeSimone et al.
patent: 5719039 (1998-02-01), Dordick et al.
patent: 5739223 (1998-04-01), DeSimone
patent: 5855819 (1999-01-01), DeSimone et al.
patent: 6025459 (2000-02-01), DeSimone et al.
Colombo et al.; “Application of structure-based thermodynamic calculations to the rationalization of the enantioselectivity of subtilisin in organic solvents,”Tetrahedron: Asymmetry9:1205-1214 (1998).
Govardhan et al.; Extremozymes for industry—from nature and by design,:Chemistry and Industry689-693 (Sep. 4, 1995).
Grim; “New technology for the preparation of peptides and peptidomimetrics,”Pharmaceutical Manufacturing International49 (1997).
Grim; “A systems approach to biocatalysis,”Pharmaceutical Manufacturing International75-76 (1996).
Grim; “From Kit to Kettle—Screening Kits and Catalysts for Biocatalytic Resolutions,”Specialty Chemicals Production, Marketing and Applications16:5 165-168 (Aug. 1996).
Khalaf et al.; “Cross-Linked Enzyme Crystals as Highly Active Catalysts in Organic Solvents,”J. Am. Chem. Soc.118:5494-5495 (1996).
Lalonde; “The Preparation of Homochiral Drugs and Peptides Using Cross-Linked Enzyme Crystals,”Chimica OGGI/chemistry today(Jun. 1995).
Lalonde et al.; “Cross-Linked Crystals ofCandida rugosaLipase: Highly Efficient Catalysts for the Resolution of Chiral Esters,”Journal of the American Chemical Society117:26 6845-6852 (1995).
Lalonde; “Practical catalysis with enzyme crystals,”Chemtech27:2 38 (1997).
Lalonde et al.; “Cross-Linked Enzyme Crystals of Lipases as Catalysts for Kinetic Resolution of Acids and Alcohols,”Methods in Enzymology286:443-464 (1997).
Lalonde; “Enzyme Catalysis: Cleaner, Safer, Energy Efficient,”Chemical Engineering108-112 (Sep. 1997).
Margolin; “Chirals boost interest in enzyme crystals,”Performance Chemicals(Apr./May 1994).
Margolin; “Novel crystalline catalysts,”TIBTECH14:7 (150) 223-230 (Jul. 1996).
Persichetti et al.; “Cross-Linked Enzyme Crystals (CLECs) of Thermolysin in the Synthesis of Peptides,”Journal of the American Chemical Society117:10 2732-2737 (1995).
Persichetti et al.; “Candida rugosaLipase: Enantioselectivity Enhancements in Organic Solvents,” Tetrahedron Letters 37:36 6507-6510 (1996).
St. Clair et al.; “Cross-Linked Enzyme Crystals as Robust Biocatalysts,” J. Am. Chem. Soc. 114:18 7314-7316 (1992).
Wang et al.; “An Efficient Synthesis of Chiral Amino Acid and Peptide Alkylamides via CLEC-Subtilisin Catalyzed Coupling and in situ Resolution,”Tetrahedron Letters37:30 5317-5320 (1996).
Wang et al.; “Cross-Linked Crystals of Subtilisin: Versatile Catalyst for Organic Synthesis,”The Journal of Organic Chemistry62:11 3488-3495 (1997).
Zmijewski et al.; “Kinetic resolutions: evaluation of a one dimensional E value calculation method using a computer and statistical software,”Tetrahedron Letters8:8 1153-1156 (1997).

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