Cytochrome P450 BM3 enzyme variants for preparation of cyclopropanes

Coelho, Pedro S.; Brustad, Eric M.; Arnold, Frances H.; Wang, Zhan; Lewis, Jared C.

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Title: Cytochrome P450 BM3 enzyme variants for preparation of cyclopropanes

Abstract

The present invention provides methods for catalyzing the conversion of an olefin to any compound containing one or more cyclopropane functional groups using heme enzymes. In certain aspects, the present invention provides a method for producing a cyclopropanation product comprising providing an olefinic substrate, a diazo reagent, and a heme enzyme; and admixing the components in a reaction for a time sufficient to produce a cyclopropanation product. In other aspects, the present invention provides heme enzymes including variants and fragments thereof that are capable of carrying out in vivo and in vitro olefin cyclopropanation reactions. Expression vectors and host cells expressing the heme enzymes are also provided by the present invention.

Inventors:: Coelho, Pedro S.; Brustad, Eric M.; Arnold, Frances H.; Wang, Zhan; Lewis, Jared C.

Issue Date:: 2021-05-18

Research Org.:: California Institute of Technology (CalTech), Pasadena, CA (United States)

Sponsoring Org.:: USDOE; National Institutes of Health (NIH)

OSTI Identifier:: 1823962

Patent Number(s):: 11008596

Application Number:: 16/246,246

Assignee:: California Institute of Technology (Pasadena, CA)

Patent Classifications (CPCs):: C - CHEMISTRY C12 - BIOCHEMISTRY C12N - MICROORGANISMS OR ENZYMES

C - CHEMISTRY C12 - BIOCHEMISTRY C12P - FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {

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C - CHEMISTRY C12 - BIOCHEMISTRY C12N - MICROORGANISMS OR ENZYMES
C12N9/0004 - {Oxidoreductases
C12N9/0042 - {NADPH-cytochrome P450 reductase

C - CHEMISTRY C12 - BIOCHEMISTRY C12P - FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {
C12P13/02 - Amides, e.g. chloramphenicol {or polyamides
C12P7/62 - Carboxylic acid esters {

C - CHEMISTRY C12 - BIOCHEMISTRY C12Y - ENZYMES
C12Y106/02004 - NADPH-hemoprotein reductase

Y - NEW / CROSS SECTIONAL TECHNOLOGIES Y02 - TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE Y02P - CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
Y02P20/52 - using catalysts, e.g. selective catalysts

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DOE Contract Number:: EB015846; FG02-06ER15762

Resource Type:: Patent

Resource Relation:: Patent File Date: 01/11/2019

Country of Publication:: United States

Language:: English

Citation Formats


                    Coelho, Pedro S., Brustad, Eric M., Arnold, Frances H., Wang, Zhan, and Lewis, Jared C. Cytochrome P450 BM3 enzyme variants for preparation of cyclopropanes.  United States: N. p., 2021. 
        Web.

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                    Coelho, Pedro S., Brustad, Eric M., Arnold, Frances H., Wang, Zhan, & Lewis, Jared C. Cytochrome P450 BM3 enzyme variants for preparation of cyclopropanes.  United States.

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                    Coelho, Pedro S., Brustad, Eric M., Arnold, Frances H., Wang, Zhan, and Lewis, Jared C. Tue .  
        "Cytochrome P450 BM3 enzyme variants for preparation of cyclopropanes".  United States.  https://www.osti.gov/servlets/purl/1823962.

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@article{osti_1823962,

  title        = {Cytochrome P450 BM3 enzyme variants for preparation of cyclopropanes},

  author       = {Coelho, Pedro S. and Brustad, Eric M. and Arnold, Frances H. and Wang, Zhan and Lewis, Jared C.},

  abstractNote = {The present invention provides methods for catalyzing the conversion of an olefin to any compound containing one or more cyclopropane functional groups using heme enzymes. In certain aspects, the present invention provides a method for producing a cyclopropanation product comprising providing an olefinic substrate, a diazo reagent, and a heme enzyme; and admixing the components in a reaction for a time sufficient to produce a cyclopropanation product. In other aspects, the present invention provides heme enzymes including variants and fragments thereof that are capable of carrying out in vivo and in vitro olefin cyclopropanation reactions. Expression vectors and host cells expressing the heme enzymes are also provided by the present invention.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2021},

  month        = {5}

}

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Title: Cytochrome P450 BM3 enzyme variants for preparation of cyclopropanes

Abstract

Citation Formats

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Substituted amino acids patent, January 1981

C-H Bond Amination and Olefin Aziridination with Beta-Diketiminato Copper Catalysts patent-application, March 2010

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Methods and systems for sulfimidation or sulfoximidation of organic molecules patent, December 2019

Method of enantioselectively inserting a carbene patent, March 1994

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P-450-Catalyzed Enantioselective Cyclopropanantion of Electron-Deficient Olefins patent-application, February 2016

Composition comprising methylphenidate and another drug patent, September 2007

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Substituted sulfones and methods of use patent-application, May 2006

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Methods and Systems for Sulfimidation or Sulfoximidation of Organic Molecules patent-application, August 2015

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Cobalt-based catalysts for the cyclization of alkenes patent-application, February 2006

In vivo and in vitro olefin cyclopropanation catalyzed by heme enzymes patent, March 2015

Intramolecular C-H amination with sulfonyl azides patent-application, March 2010

Tailored Control of Surface Properties by Chemical Modification patent-application, March 2010

Compounds and Pharmaceutical Compositions for the Treatment of Viral Infections patent-application, September 2009

Modified Drugs for Use in Liposomal Nanoparticles patent-application, September 2012

Cytochrome C protein variants for catalyzing carbon-silicon bond formation patent, October 2018

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Preparation of derivatives of cyclobutane and cyclobutene patent, June 1976

Method of Producing 6,6Dimethyl-3-Oxabicyclo[3.1.0] Hexan-2-One patent-application, July 2010

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Process for the preparation of an oxirane, azirdine or cyclopropane
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Active Substance Combinations with Insecticidal Properties
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Mutant Enzymes
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Substituted amino acids
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C-H Bond Amination and Olefin Aziridination with Beta-Diketiminato Copper Catalysts
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Rubber Composition
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Method of enantioselectively inserting a carbene
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Borazine-based resin, and method for production thereof, borazine based resin composition, insulating coating and method for formation thereof, and electronic parts having the insulating coating
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Regio- and enantioselective alkane hydroxylation with modified cytochrome P450
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