Bioconversion process for producing nylon-7, nylon-7,7 and polyesters

Patent metadata

Field	Value
Publication number	US-10689673-B2
Application number	US-201214367484-A
Country	US
Kind code	B2
Filing date	Dec 21, 2012
Priority date	Jun 30, 2011
Publication date	Jun 23, 2020
Grant date	Jun 23, 2020

Abstract

Embodiments of the present invention relate to methods for the biosynthesis of di- or trifunctional C7 alkanes in the presence of isolated enzymes or in the presence of a recombinant host cell expressing those enzymes. The di- or trifunctional C7 alkanes are useful as intermediates in the production of nylon-7, nylon-7,x, nylon-x,7, and polyesters.

First claim

We claim:

1. A method of converting a compound, the method comprising contacting pimeloyl-CoA (PCoA) or pimeloyl acyl carrier protein (PACP) with a single enzyme that catalyzes the reduction of PCoA or PACP to pimelic acid semialdehyde (PAS) in a single reaction, wherein PAS is produced, and wherein the single enzyme that catalyzes the reduction of PCoA or PACP to PAS in a single reaction is a fatty-acyl-CoA reductase in EC 1.2.1.3, EC 1.2.1.10, EC 1.2.1.22, EC 1.2.1.50, or EC 1.2.1.76, a fatty-acyl-[acp]-reductase in EC 1.2.1.80, or an aldehyde dehydrogenase in EC 1.2.1.10, EC 1.2.1.76, or EC 1.2.1.50.

2. The method of claim 1 , wherein the PCoA is produced by a process comprising one or more steps selected from:
(a) converting meso-2,6-diaminopimelate to 6-amino-2-heptendioic acid using an ammonia lyase;
(b) converting 6-amino-2-heptendioic acid to 2-amino-heptendioic acid using an enolate reductase;
(c) converting 2-amino-heptendioic acid to α-ketopimelate using an amino transferase;
(d) converting α-ketopimelate to α-hydroxypimelate using a carbonyl reductase;
(e) converting α-hydroxypimelate to 2-heptanedioic acid using a hydrolase;
(f) converting 2-amino-heptendioic acid to 2-heptenedioic acid using an ammonia lyase;
(g) converting 2-heptenedioic acid to 2-heptenedioic acid-CoA using a CoA transferase acid thiol ligase; and
(h) converting 2-heptenedioic acid-CoA to PCoA using an enolate reductase CoA dehydrogenase;
or any one of the steps chosen from:
(i) converting α-hydroxypimelate to α-hydroxypimeloyl-CoA using a CoA transferase acid-thiol ligase;
(j) converting α-hydroxypimelate to 2-heptenedioic acid using a hydrolase;
(k) converting 2-heptenedioic acid to 2-heptenedioic acid-CoA using a CoA transferase acid-thiol ligase;
(l) converting α-hydroxypimeloyl-CoA to 2-heptendioic acid-CoA using a hydrolase; and
(m) converting 2-heptendioic acid-CoA to PCoA using an enolate reductase.

3. The method of claim 1 , wherein the single enzyme is isolated and purified.

4. The method of claim 1 , wherein the PACP is produced by a process comprising one or more steps selected from:
(a) converting malonyl-CoA to malonyl-CoA methyl ester using an enzyme in EC 2.1.1.197;
(b) converting malonyl-CoA methyl ester to 3-oxo-glutaryl-[acp]methyl ester using an enzyme in EC 2.3.1.180;
(c) converting 3-oxo-glutaryl-[acp]methyl ester to 3-hydroxy-glutaryl-[acp]methyl ester using an enzyme in EC 1.1.1.100;
(d) converting 3-hydroxy-glutaryl-[acp]methyl ester to enoylglutaryl-[acp]methyl ester using an enzyme in EC 4.2.1.59;
(e) converting enoylglutaryl-[acp]methyl ester to glutaryl-[acp]methyl ester using an enzyme in EC 1.3.1.10;
(f) converting glutaryl-[acp]methyl ester to 3-oxopimelyl-[acp]methyl ester using an enzyme in EC 2.3.1.41;
(g) converting 3-oxopimelyl-[acp]methyl ester to 3-hydroxypimelyl-[acp]methyl ester using an enzyme in EC 1.1.1.100;
(h) converting 3-hydroxypimelyl-[acp]methyl ester to enoylpimelyl-[acp]methyl ester using an enzyme in EC 4.2.1.59;
(i) converting enoylpimelyl-[acp]methyl ester to pimelyl-[acp]methyl ester using an enzyme in EC 1.3.1.10; and
(i) converting pimelyl-[acp]methyl ester to PACP using an enzyme in EC 3.1.1.85.

5. The method of claim 1 , wherein the PCoA or PACP is produced by a process comprising one or more steps selected from:
(a) converting a long-chain fatty acid-[acp] to PACP using a P450BioI enzyme;
(b) converting PACP to pimelic acid; and
(c) converting pimelic acid to PCoA using an enzyme in EC 6.2.1.14.

6. The method of claim 1 , wherein the PCoA is produced by a process comprising one or more steps of selected from:
(a) converting benzoate to benzoyl-CoA using an enzyme in EC 6.2.1.25;
(b) converting benzoyl-CoA to 2-ketocyclohexane-1-carboxyl-CoA;
(c) converting cyclohexane carboxylate to 2-ketocyclohexane-1-carboxyl-CoA; and
(d) converting to 2-ketocyclohexane-1-carboxyl-CoA to PCoA using 2-ketocyclohexanecarboxyl-CoA hydrolase.

7. The method of claim 1 , wherein the PCoA is produced by a process comprising one or more steps selected from:
(a) converting crotonate to crotonyl-CoA;
(b) converting crotonyl-CoA to 3-hydroxy-butyryl-CoA using an enzyme in EC 4.2.1.17;
(c) converting 3-hydroxy-butyryl-CoA to aceto-acetyl-CoA using an enzyme in EC 1.1.1.157;
(d) converting aceto-acetyl-CoA to acetyl-CoA;
(e) converting acetyl-CoA to aceto-acetyl-CoA using an enzyme in EC 2.3.1.9;
(f) converting aceto-acetyl-CoA to 3-hydroxy-butyryl-CoA;
(g) converting 3-hydroxy-butyryl-CoA to crotonyl-CoA;
(h) converting crotonyl-CoA to

(i) converting

(j) converting

(k) converting

(l) converting

(m) converting

to pimeloyl-CoA; and
(n) converting pimeloyl-CoA to cyclohexane carboxylate.

8. The method of claim 1 , wherein the PCoA is produced by a process comprising one or more steps selected from:
(a) converting malonyl-CoA to 3-oxoglutaryl-CoA;
(b) converting 3-oxoglutaryl-CoA to glutaryl-CoA; and
(c) converting glutaryl-CoA to PCoA.

Assignees

• Invista North America Sarl

Inventors

• Pearlman Paul S
• Chen Changlin
• Botes Adriana L
• Conradie Alex Van Eck
• Herzog Benjamin D

Classifications

• C08G69/28

  Preparatory processes · CPC title

• C12Y301/0202

  Acyl-CoA hydrolase (3.1.2.20) · CPC title

• C12N9/16

  acting on ester bonds (3.1) · CPC title

• B29B9/16

  Auxiliary treatment of granules · CPC title

• C12N9/93

  Ligases (6) · CPC title