Title: In vivo and in vitro olefin cyclopropanation catalyzed by heme enzymes

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:

2016-11-15

Research Org.:

California Institute of Technology (CalTech), Pasadena, CA (United States)

Sponsoring Org.:

USDOE

OSTI Identifier:

1332273

Patent Number(s):

9493799

Application Number:

14/625,449

Assignee:

CALIFORNIA INSTITUTE OF TECHNOLOGY (Pasadena, CA)

Patent Classifications (CPCs):

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

C - CHEMISTRY C12 - BIOCHEMISTRY C12Y - ENZYMES

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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

C - CHEMISTRY C12 - BIOCHEMISTRY C12Y - ENZYMES

C12Y106/02004 - NADPH-hemoprotein reductase

C - CHEMISTRY C12 - BIOCHEMISTRY C12N - MICROORGANISMS OR ENZYMES

C12N9/0004 - {Oxidoreductases

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

C - CHEMISTRY C12 - BIOCHEMISTRY C12N - MICROORGANISMS OR ENZYMES

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 {

C12P7/62 - Carboxylic acid esters {

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DOE Contract Number:  

FG02-06ER15762

Resource Type:

Patent

Resource Relation:

Patent File Date: 2015 Feb 18

Country of Publication:

United States

Language:

English

Subject:

59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY