US 11,268,110 B2Granted

Methods and materials for the enzymatic conversion of a non-3-enal to azelaic acid

AssigneeINV Nylon Chemicals Americas, LLC

InventorsAlex Van Eck Conradie, Adriana L. Botes, Alexander Brett Foster, Changlin Chen

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Abstract

This document describes biochemical pathways for producing pimeloyl-CoA using a polypeptide having the enzymatic activity of a hydroperoxide lyase to form non-3-enal and 9-oxononanoate from 9-hydroxyperoxyoctadec-10,12-dienoate. Non-3-enal and 9-oxononanoate can be enzymatically converted to pimeloyl-CoA or a salt thereof using one or more polypeptides having the activity of a dehydrogenase, a CoA ligase, an isomerase, a reductase, a thioesterase, a monooxygenase, a hydratase, and/or a thiolase. Pimeloyl-CoA can be enzymatically converted to pimelic acid, 7-aminoheptanoic acid, 7-hydroxyheptanoic acid, heptamethylenediamine, or 1,7-heptanediol, or corresponding salts thereof. This document also describes recombinant microorganisms producing pimeloyl-CoA, as well as pimelic acid, 7-aminoheptanoic acid, 7-hydroxyheptanoic acid, heptamethylenediamine, and 1,7-heptanediol, or corresponding salts thereof.

Claims21

Dependent claims

A method of producing azelaic acid, said method comprising:

enzymatically converting a 9-hydroxyperoxyoctadec-10,12-dienoate to non-3-enal and 9-oxononanoate in a recombinant Escherichia coli microorganism and in the presence of a carbon source, wherein the recombinant Escherichia coli microorganism has been transformed to express an exogenous polypeptide having the activity of a hydroperoxide lyase and at least 85% sequence identity to the polypeptide of SEQ ID NO:
13 or SEQ ID NO:
14;
and
enzymatically converting the non-3-enal to azelaic acid in the recombinant Escherichia coli microorganism and in the presence of a carbon source, wherein the recombinant Escherichia coli microorganism has been transformed to express one or more polypeptides comprising at least one polypeptide having the activity of a dodecenoyl-CoA isomerase and at least 85% sequence identity to the polypeptide of SEQ ID NO:
17 or at least one polypeptide having the activity of an enoate reductase and at least 85% sequence identity to the polypeptide of SEQ ID NO:
15 or SEQ ID NO:
16.

5 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/656,816Filed 18 Oct 2019 · continuation
Priority: 1 Feb 2016
Published: US 2020/0277634 A13 Sep 2020
Granted: 8 Mar 2022
Term ends: Not estimatedThe source records don’t support an estimate.

Classification32 codes

C12P 7/40
Preparation of oxygen-containing organic compounds: containing a carboxyl group including Peroxycarboxylic acids
C07C 47/21
Unsaturated compounds having —CHO groups bound to acyclic carbon atoms: with only carbon-to-carbon double bonds as unsaturation
C07C 59/147
Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, [IMAGE…: saturated…
C08G 69/10
Derived from amino-carboxylic acids: alpha-amino-carboxylic acids

Family

Application62/289,877Us provisional application · filed 1 Feb 2016
Application15/421,164Parent of this continuation · filed 31 Jan 2017
Application16/351,324Parent of this continuation · filed 12 Mar 2019
US 2020/0277634 A1Pre-grant publication · published 3 Sep 2020
US 2017/0218406 A1Published application
US 11,268,110 B2This patent

From the US filing history. Foreign family members aren’t listed.