1. WO2016176339 - SYNTHESIS OF OMEGA-PHENYL PRODUCTS AND DERIVATIVES THEREOF

Publication Number WO/2016/176339

Publication Date 03.11.2016

International Application No. PCT/US2016/029583

International Filing Date 27.04.2016

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Applicants

• WILLIAM MARSH RICE UNIVERSITY [US]/[US]

Inventors

• GONZALEZ, Ramon
• CHEONG, Seokjung
• CLOMBURG, James, M.

Agents

• VALOIR, Tamsen

Priority Data

62/154,010

28.04.2015

US

Publication Language English (en)

Filing Language English (en)

Designated States

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AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
African Regional Intellectual Property Organization (ARIPO) (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, RU, TJ, TM)
European Patent Office (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG)

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Title

(EN) SYNTHESIS OF OMEGA-PHENYL PRODUCTS AND DERIVATIVES THEREOF

(FR) SYNTHÈSE DE PRODUITS À FONCTION OMÉGA-PHÉNYLE ET DÉRIVÉS DE CEUX-CI

Abstract

(EN) This disclosure generally relates to the use of microorganisms to make omega-phenyl products, including omega-phenyl carboxylic acids, alcohols, amines, methyl ketones and their beta-functionalized derivatives. This is achieved by utilizing an iterative carbon chain elongation pathway that uses omega-phenyl CoA thioester primers. The core enzymes in the pathway include thiolase, dehydrogenase, dehydratase and reductase. Native or engineered thiolases catalyze the condensation of omega-phenyl CoA thioester primers with acetyl-CoA as the extender unit to generate omega-phenyl β-keto acyl-CoA. Dehydrogenase converts omega-phenyl β-keto acyl-CoA to omega-phenyl β-hydroxy acyl-CoA. Dehydratase converts omega-phenyl β-hydroxy acyl-CoA to omega-phenyl enoyl-CoA. Reductase converts omega- phenyl enoyl-CoA to omega-phenyl acyl-CoA. The platform can be operated in an iterative manner (i.e. multiple turns) by using the resulting omega-phenyl acyl-CoA as primer and acetyl-CoA as extender unit in subsequent turns of the cycle. Termination pathways acting on any of the four omega-phenyl CoA thioester intermediates terminate the platform and generate various omega-phenyl carboxylic acids, alcohols, and amines with different degrees of β -reduction.

(FR) La présente invention concerne d'une façon générale l'utilisation de microorganismes pour la fabrication de produits à fonction oméga-phényle, y compris d'acides oméga-phénylcarboxiliques, d'alcools à fonction oméga-phényle, d'amines à fonction oméga-phényle, de méthylcétones à fonction oméga-phényle et de leurs dérivés bêta-fonctionnalisés. Cela est réalisé en utilisant une voie itérative d'allongement des chaînes carbonées qui utilise des amorces de type thioester CoA à fonction oméga-phényle. Les enzymes au cœur de cette voie comprennent la thiolase, la déshydrogénase, la déshydratase et la réductase. Des thiolases natives ou génétiquement modifiées catalysent la condensation d'amorces de type thioester CoA à fonction oméga-phényle, l'acétyle-CoA servant de motif extenseur pour générer de la β-céto acyle-CoA à fonction oméga-phényle. Une déshydrogénase convertit la β-céto acyle-CoA à fonction oméga-phényle en β-hydroxy acyle-CoA à fonction oméga-phényle. Une déshydratase convertit la β-hydroxy acyle-CoA à fonction oméga-phényle en énoyl-CoA à fonction oméga-phényle. Une réductase convertit l'énoyl-CoA à fonction oméga-phényle en acyle-CoA à fonction oméga-phényle. La plate-forme peut être actionnée de manière itérative (c'est-à-dire à de multiples reprises) en utilisant l'acyle-CoA à fonction oméga-phényle résultante en tant qu'amorce et l'acétyle-CoA en tant que motif extenseur dans la suite du cycle. Des voies de terminaison agissant sur l'un quelconque des quatre intermédiaires de type thioester CoA à fonction oméga-phényle mettent fin à la plate-forme et génèrent divers acides oméga-phénylcarboxiliques, alcools à fonction oméga-phényle et amines à fonction oméga-phényle présentant divers degrés de réduction β.

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