Methods for biosynthesizing 1,3 butadiene

Patent metadata

Field	Value
Publication number	US-2016355844-A1
Application number	US-201615213830-A
Country	US
Kind code	A1
Filing date	Jul 19, 2016
Priority date	Jun 17, 2011
Publication date	Dec 8, 2016
Grant date	—

Abstract

This document describes biochemical pathways for producing butadiene by forming two vinyl groups in a butadiene synthesis substrate. These pathways described herein rely on enzymes such as mevalonate diphosphate decarboxylase, isoprene synthase, and dehydratases for the final enzymatic step.

First claim

1 . A method for the biosynthesis of butadiene, said method comprising forming two terminal vinyl groups in a butadiene synthesis substrate.

2 . The method of claim 1 , wherein a first vinyl group is enzymatically formed in said butadiene synthesis substrate to produce a compound selected from the group consisting of 2-oxopent-4-enoate, propenyl-CoA, (R) 3-hydroxypent-4-enoate, 2,4-pentadienoyl-[acp], 2,4-pentadienoyl-CoA, crotonyl-CoA, and 3-buten-2-ol.

3 . The method of claim 2 , wherein 2-oxopent-4-enoate is produced by forming a first vinyl group in (i) 4-oxalocrotonate using an 4-oxalocrotonate decarboxylase classified in EC 4.1.1.77, (ii) 2-hydroxymuconate semialdehyde using a 2-hydroxymuconate-semialdehyde hydrolase classified in EC 3.7.1.9, (iii) 2-hydroxy-6-oxonona-2,4-diene-1,9-dioate using a 2-hydroxy-6-oxonona-2,4-dienedioate hydrolase classified in EC 3.7.1.14 ,or (iv) by converting 2-hydroxymuconate semialdehyde to 2-hydroxymuconate using a 2 aminomuconate semialdehyde dehydrogenase classified under EC 1.2.1.32, converting 2-hydroxymuconate to 4-oxalocrotonate using a 2-hydroxymuconate tautomerase classified under EC 5.3.2.6, and converting 4-oxalocrotonate to 2-oxopent-4-enoate using a 4-oxalocrotonate decarboxylase classified under EC 4.1.1.77.

4 . (canceled)

5 . The method according to claim 3 , wherein (i) 2-hydroxymuconate semialdehyde is produced by converting catechol to 2-hydroxymuconate semilaldehyde using a catechol 2,3-dioxygenase classified under EC 1.13.11.2, (ii) 2-hydroxymuconate semialdehyde is produced by converting 5-carboxy-2-hydroxymuconate-6-semiadehyde using a 5-carboxy-2-hydroxymuconate-6-semialdehyde decarboxylase or (iii) 2-hydroxy-6-oxonona-2,4-diene-1,9-dioate is produced by converting 2,3-dihydroxy phenylpropionate using a 3-carboxyethylcatechol 2,3-dioxygenase classified under EC 1.13.11.16.

6 . The method according to claim 5 , wherein said catechol is produced by converting anthranilate using an anthranilate 1,2-dioxygenase classified under EC 1.14.12.1 or by converting protocatechuate using a protocatechuate decarboxylase classified under EC 4.1.1.63; said 5-carboxy-2-hydroxymuconate-6-semialdehyde decarboxylase is encoded by praH or produced by converting protocatechuate using a protocatechuate 2,3-dioxygenase, wherein said protocatechuate 2,3-dioxygenase is optionally encoded by praA; or said 2,3-dihydroxyphenylpropionate is produced by converting cis-3-(carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol using a 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl) propanoate dehydrogenase classified under EC 1.3.1.87.

7 . The method of claim 6 , wherein anthranilate is produced by converting chorismate using an anthranilate synthase classified under EC 4.1.3.27 or protocatechuate is produced by converting 3-dehydroshikimate using a 3-dehydroshikimate dehydratase classified under EC 4.2.1.118.

8 - 13 . (canceled)

14 . The method of claim 6 , wherein 2,3-dihydroxyphenylpropionate is produced by converting cis-3-(carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol using a 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl) propanoate dehydrogenase classified under EC 1.3.1.87; wherein cis-3-(carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol is produced by converting 3-phenyl-propionate using a 3-phenylpropanoate dioxygenase classified under EC 1.14.12.19; wherein 3-phenyl-propionate is produced by converting E-cinnamate using a 2-enoate reductase classified under EC 1.3.1.31; and/or wherein E-cinnamate is produced by converting L-phenylalanine using a phenylalanine ammonia-lyase classified under EC 4.3.1.24.

15 - 17 . (canceled)

18 . The method according to claim 1 , where said butadiene synthesis substrate is propanoyl-CoA.

19 . The method according to claim 18 , where propenoyl-CoA is the compound that is produced by forming a first vinyl group in (i) propanoyl-CoA using a butyryl-CoA dehydrogenase classified under EC 1.3.8.1 or a medium-chain acyl-CoA dehydrogenase classified under EC 1.3.8.7, where propanoyl-CoA is optionally produced by converting (2S)-methylmalonyl-CoA using a methylmalonyl-CoA carboxytransferase classified under EC 2.1.3.1 or a methylmalonyl-CoA decarboxylase classified under EC 4.1.1.41; (ii) lactoyl-CoA using a lactoyl-CoA dehydratase classified under EC 4.2.1.54, where lactoyl-CoA is optionally produced by converting L-lactate using a proprionate CoA-transferase classified under EC 2.8.3.1, wherein produced by converting pyruvate using an L-lactate dehydrogenase classified under EC 1.1127 or (iii) 3-hydroxypropionyl-CoA using a 3-hydroxypropionyl-CoA dehydratase classified under EC 4.2.1.116, wherein 3-hydroxypropionyl-CoA is optionally produced by converting 3-hydroxypropionate using a 3-hydroxyisobutyryl-CoA hydrolase classified under EC 3.1.2.4 or by converting malonate semialdehyde using a 3-hydroxyprobionate dehydrogenase EC 1.1.1.59, wherein malonate semiladehyde is optionally produced by converting malonyl-CoA using a malonyl-CoA reductase classified under EC 1.2.1.75; by converting 2-oxo-butyrate using a 2-ketobutyrate formate-lyase classified under EC 2.3.1.-, wherein said 2-ketobutyrate formate-lyase is optionally encoded by tdcE or wherein 2-oxo-butryate is optionally produced by converting L-threonine using a threonine ammonia lyase classified under EC 4.3.1.19; by converting propanol using a propionaldehyde dehydrogenase wherein said propionaldehyde dehydrogenase is optionally encoded by pduP or wherein propanol is optionally produced by converting 1,2-propanediol using a propanediol dehydratase classified under EC 4.2.1.28; from levulinic acid by converting levulinyl-CoA using a transferase classified under EC 2.3.1.-, wherein levulinyl-CoA is optionally produced by converting levulinyl acid using an acyl-CoA synthetase or ligase classified under EC 6.2. 1.-; or by converting propenoyl-CoA using a butyryl-CoA dehydrogenase classified under EC 1.3.8.1 or a medium-chain acyl-CoA dehydrogenase classified under EC 1.3.8.7.

20 . (canceled)

21 . The method of claim 19 , wherein (2S)-methylmalonyl-CoA is produced by converting (2R)-methylmalonyl-CoA using a methylmalonyl-CoA epimerase classified under EC 5.1.99.1; and/or wherein (2R)-methylmalonyl-CoA is produced by converting succinyl-CoA using a methylmalonyl-CoA mutase classified under EC 5.4.99.2.

22 - 36 . (canceled)

37 . The method of claim 2 , where (R) 3-hydroxypent-4-enoate propenoyl-CoA is produced by forming a first vinyl in (R) 3-hydroxypentanoate using a desaturase/monooxygenas, wherein said desaturase is optionally a gene product of MdpJ e, or cytochrome P450, wherein said cytochrome P450 is optionally a gene product of the CYP4 family, wherein (R) 3-hydroxy-pentanoate is optionally produced by converting (R) 3-hydroxypentanoyl-CoA using a thioesterase classified under EC 3.1.2.-, wherein said thioesterase is optionally a gene product of tesB, wherein (R) 3-hydroxypentanoyl-CoA is optionally produced by converting 3-oxopentanoyl-CoA using an acetoacetyl-CoA reductase classified under EC 1.1.1.36, wherein said acetoacetyl-CoA reductase is optionally a gene product of phaB and/or wherein 3-oxopentanoyl-CoA is optionally produced by converting propanoyl-CoA u sing an acetyl-CoA C-acyltrans erase classified under EC 2.3.1.16.

38 - 40 . (canceled)

41 . The method of claim 2 , wherein 2,4-pentadienoyl-[acp] is produced by forming a first vinyl group in pent-2-enoyl-acp using an acyl-[acp] dehydrogenase, wherein pent-2-enoyl-[acp] is optionally produced by converting (R) 3-hydroxypentanoyl-[acp] using a 3-Hydroxyacyl-[acp] dehydratase classified under EC 4.2.1.59 or by co

Assignees

• Invista North America Sarl

Inventors

• Pearlman Paul S
• Chen Changlin
• Botes Adriana Leonora
• Conradie Alex Van Eck

Classifications

• C12Y401/01033

  Diphosphomevalonate decarboxylase (4.1.1.33), i.e. mevalonate-pyrophosphate decarboxylase · CPC title

• C12N15/52

  Genes encoding for enzymes or proenzymes · CPC title

• C12Y402/01127

  Linalool dehydratase (4.2.1.127) · CPC title

• C12P5/026 Primary

  Unsaturated compounds, i.e. alkenes, alkynes or allenes · CPC title

• C12N9/88

  Lyases (4.) · CPC title