WO2016210352A3 - Synthesis of pheromones and other oxy-functionalized products via enzymatic hydroxylation of carboxylic acids - Google Patents

Synthesis of pheromones and other oxy-functionalized products via enzymatic hydroxylation of carboxylic acids Download PDF

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Publication number
WO2016210352A3
WO2016210352A3 PCT/US2016/039399 US2016039399W WO2016210352A3 WO 2016210352 A3 WO2016210352 A3 WO 2016210352A3 US 2016039399 W US2016039399 W US 2016039399W WO 2016210352 A3 WO2016210352 A3 WO 2016210352A3
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WO
WIPO (PCT)
Prior art keywords
oxy
pheromones
product
synthesis
carboxylic acids
Prior art date
Application number
PCT/US2016/039399
Other languages
French (fr)
Other versions
WO2016210352A2 (en
Inventor
Vu Bui
Pedro COELHO
Mike M.Y. Chen
Peter Meinhold
Thomas HEEL
Original Assignee
Provivi, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Provivi, Inc. filed Critical Provivi, Inc.
Publication of WO2016210352A2 publication Critical patent/WO2016210352A2/en
Publication of WO2016210352A3 publication Critical patent/WO2016210352A3/en

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/62—Carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y114/00—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14)
    • C12Y114/14—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14) with reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen (1.14.14)
    • C12Y114/14001—Unspecific monooxygenase (1.14.14.1)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y114/00—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14)
    • C12Y114/15—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14) with reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen (1.14.15)
    • C12Y114/15003—Alkane 1-monooxygenase (1.14.15.3)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • General Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The present invention provides a method for synthesizing an oxyfunctionalized product. The method includes incubating an enzyme substrate with an enzyme capable of hydroxylating one terminal carbon of the enzyme substrate to form a hydroxylated product and converting at least a portion of the hydroxylated product to the oxyfunctionalized product. The enzyme substrate is an unsaturated or saturated carboxylic acid or an ester thereof, and the hydroxylated product can be a terminal hydroxy-substituted unsaturated carboxylic acid or an ester thereof. The oxy-functionalized products include insect pheromones and other useful compounds.
PCT/US2016/039399 2015-06-24 2016-06-24 Synthesis of pheromones and other oxy-functionalized products via enzymatic hydroxylation of carboxylic acids WO2016210352A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201562184068P 2015-06-24 2015-06-24
US62/184,068 2015-06-24

Publications (2)

Publication Number Publication Date
WO2016210352A2 WO2016210352A2 (en) 2016-12-29
WO2016210352A3 true WO2016210352A3 (en) 2017-02-02

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2016/039399 WO2016210352A2 (en) 2015-06-24 2016-06-24 Synthesis of pheromones and other oxy-functionalized products via enzymatic hydroxylation of carboxylic acids

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WO (1) WO2016210352A2 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109022473B (en) * 2018-08-13 2021-09-17 浙江海洋大学 Method for preparing orlistat intermediate by enzyme method
CN109097344B (en) * 2018-08-07 2021-10-22 浙江海洋大学 Marine sphingolipid bacteria short-chain alcohol dehydrogenase mutant and application thereof

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110343675B (en) * 2018-04-04 2023-05-12 上海凯赛生物技术股份有限公司 Directed evolution of CYP52A12 gene and application thereof in dibasic acid production
CN112126592B (en) * 2020-08-06 2022-06-14 浙江工业大学 Hirsutella sinensis mutant strain and application thereof in nucleoside production
CN113861021B (en) * 2021-10-28 2024-01-30 海南师范大学 Unsaturated fatty acid compound, and separation method and application thereof

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
AIRD ET AL.: "An Evans-Tishchenko-Ring-Closing Metathesis Approach to Medium-Ring Lactones", ORGANIC LETTERS, vol. 9, no. 4, 2007, pages 631 - 634, XP055351909 *
BINDER ET AL.: "Combining Ring-Opening Metathesis Polymerization (ROMP) with Sharpless- Type 'Click' Reactions: An Easy Method for the Preparation of Side Chain Functionalized Poly(oxynorbornenes", MACROMOLECULES, vol. 37, 2004, pages 9321 - 9330, XP055216365 *
CRYLE ET AL.: "Products of Cytochrome P450biol (CYP107H1)-catalyzed Oxidation of Fatty Acids", ORGANIC LETTERS, vol. 5, 2003, pages 3341 - 3344, XP055110648 *
ISHIGAMI: "Synthetic Studies of Natural 10-Membered Lactones, Mueggelone, Microcarpalide, and Sch 642305, Which Have Interesting Bioactivities", BIOSCI. BIOTECHNOL. BIOCHEM., vol. 73, no. 5, 2009, pages 971 - 979, XP055351908 *
KATO ET AL.: "Regio- and stereoselective hydroxylation of 10-undecenoic acid with a light-driven P450 BM3 biocatalyst yielding a valuable synthon for natural product synthesis", BIOORGANIC AND MEDICINAL CHEMISTRY, vol. 22, no. 20, 2014, pages 5687 - 5691, XP029071534 *
REDDY ET AL.: "Stereoselective Total Synthesis of the Natural Oxylipin (6R,7E,9R,10S)-6,9,10- Trihydroxyoctadec-7-enoic Acid'.", HELVETICA CHIMICA ACTA, JANUARY, vol. 98, 2015, pages 78 - 84, XP055351900 *
SINGH ET AL.: "Transesterification/Acylation of Secondary Alcohols Mediated by N-Heterocyclic Carbene Catalysts", J. ORG. CHEM., vol. 69, 2004, pages 209 - 212, XP055016169 *
STARKS ET AL.: "Selective Catalytic Dehydration of 2-alcohols; A new Synthesis of 1-Olefins", J. AM. CHEM. SOC., vol. 85, no. 14, 1963, pages 2180 - 2181, XP055034366 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109097344B (en) * 2018-08-07 2021-10-22 浙江海洋大学 Marine sphingolipid bacteria short-chain alcohol dehydrogenase mutant and application thereof
CN109022473B (en) * 2018-08-13 2021-09-17 浙江海洋大学 Method for preparing orlistat intermediate by enzyme method

Also Published As

Publication number Publication date
WO2016210352A2 (en) 2016-12-29

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