US20110118433A1 - Candida tropicalis cells and use thereof - Google Patents

Candida tropicalis cells and use thereof Download PDF

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Publication number
US20110118433A1
US20110118433A1 US12/943,145 US94314510A US2011118433A1 US 20110118433 A1 US20110118433 A1 US 20110118433A1 US 94314510 A US94314510 A US 94314510A US 2011118433 A1 US2011118433 A1 US 2011118433A1
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seq
candida tropicalis
cell
hydroxycarboxylic acid
gene
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Markus Pötter
Hans-Georg Hennemann
Steffen Schaffer
Thomas Haas
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Evonik Operations GmbH
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Evonik Degussa GmbH
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Assigned to EVONIK DEGUSSA GMBH reassignment EVONIK DEGUSSA GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HAAS, THOMAS, SCHAFFER, STEFFEN, HENNEMANN, HANS-GEORG, POETTER, MARKUS
Publication of US20110118433A1 publication Critical patent/US20110118433A1/en
Priority to US13/764,996 priority Critical patent/US8999684B2/en
Priority to US14/609,714 priority patent/US9150890B2/en
Abandoned legal-status Critical Current

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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
    • C12P7/62—Carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/14—Fungi; Culture media therefor
    • C12N1/16—Yeasts; Culture media therefor
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
    • C07C67/42—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester by oxidation of secondary alcohols or ketones
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0012—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7)
    • C12N9/0036—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7) acting on NADH or NADPH (1.6)
    • C12N9/0038—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7) acting on NADH or NADPH (1.6) with a heme protein as acceptor (1.6.2)
    • C12N9/004—Cytochrome-b5 reductase (1.6.2.2)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0012—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7)
    • C12N9/0036—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7) acting on NADH or NADPH (1.6)
    • C12N9/0038—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7) acting on NADH or NADPH (1.6) with a heme protein as acceptor (1.6.2)
    • C12N9/0042—NADPH-cytochrome P450 reductase (1.6.2.4)
    • 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
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/04—Alpha- or beta- amino acids
    • 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
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/42—Hydroxy-carboxylic acids
    • 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
    • C12P7/625—Polyesters of hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y101/00—Oxidoreductases acting on the CH-OH group of donors (1.1)
    • C12Y101/01—Oxidoreductases acting on the CH-OH group of donors (1.1) with NAD+ or NADP+ as acceptor (1.1.1)
    • C12Y101/01001—Alcohol dehydrogenase (1.1.1.1)

Definitions

  • the invention relates to genetically engineered Candida tropicalis cells, use thereof and a method of production of ⁇ -hydroxycarboxylic acids and ⁇ -hydroxycarboxylic acid esters.
  • Candida tropicalis Owing to its ability to form dicarboxylic acids from alkanes, Candida tropicalis is a well-characterized ascomycete.
  • WO91/006660 describes Candida tropicalis cells that are completely inhibited in ⁇ -oxidation through interruption of the POX4 and/or POX5 genes, and achieve increased yields of ⁇ , ⁇ -dicarboxylic acids.
  • WO00/020566 describes cytochrome P450 monooxygenases and NADPH cytochrome P450 oxidoreductases from Candida tropicalis and use thereof for influencing ⁇ -hydroxylation, the first step in ⁇ -oxidation.
  • WO03/089610 describes enzymes from Candida tropicalis which catalyse the second step of ⁇ -oxidation, the conversion of a fatty alcohol to an aldehyde, and use thereof for improved production of dicarboxylic acids.
  • ⁇ -Hydroxycarboxylic acids and their esters are economically important compounds as precursors of polymers, and this forms the basis of the commercial usability of the present invention.
  • the task of the invention was to find a way of preparing ⁇ -hydroxycarboxylic acids or ⁇ -hydroxycarboxylic acid esters by fermentation in sufficient amounts, in particular in the medium surrounding the cells.
  • the object of the present invention is therefore a cell as described in claim 1 .
  • Another object of the invention is the use of the cell according to the invention and a method of production of ⁇ -hydroxycarboxylic acids and ⁇ -hydroxycarboxylic acid esters using the cells according to the invention.
  • Advantages of the invention are the gentle conversion of the educt used to the ⁇ -hydroxycarboxylic acids and corresponding esters and a high specificity of the method and an associated high yield based on the educt used.
  • One object of the present invention is a Candida tropicalis cell, in particular one from the strain ATCC 20336, which is characterized in that the cell has, compared with its wild type, a reduced activity of at least one of the enzymes that are encoded by the intron-free nucleic acid sequences selected from the two group comprising
  • Seq ID No. 1 Seq ID No. 3, Seq ID No. 5, Seq ID No. 7, Seq ID No. 9, Seq ID No. 11, Seq ID No. 13, Seq ID No. 15, Seq ID No. 17, Seq ID No. 19, Seq ID No. 21, Seq ID No. 23, Seq ID No. 25, Seq ID No. 27, Seq ID No. 29, Seq ID No. 31, Seq ID No. 33, Seq ID No. 35, Seq ID No. 37, Seq ID No. 39, Seq ID No. 41, Seq ID No. 43, Seq ID No. 45, Seq ID No. 47, Seq ID No. 49, Seq ID No. 51, Seq ID No. 53, Seq ID No. 55, Seq ID No.
  • Seq ID No. 59 Seq ID No. 61, Seq ID No. 63, Seq ID No. 65 and Seq ID No. 67; in particular Seq ID No. 1, Seq ID No. 3, Seq ID No. 5, Seq ID No. 7, Seq ID No. 9, Seq ID No. 11, Seq ID No. 13, Seq ID No. 15, Seq ID No. 17, Seq ID No. 19, Seq ID No. 21, Seq ID No. 23, Seq ID No. 25, Seq ID No. 27, Seq ID No. 29, Seq ID No. 31, Seq ID No. 33, Seq ID No. 35, Seq ID No. 37, Seq ID No. 39, Seq ID No. 41, Seq ID No. 43, Seq ID No.
  • Seq ID No. 47, Seq ID No. 49 and Seq ID No. 51 are quite especially Seq ID No. 1, Seq ID No. 3, Seq ID No. 5, Seq ID No. 7, Seq ID No. 9, Seq ID No. 11, Seq ID No. 13, Seq ID No. 15, Seq ID No. 17, Seq ID No. 19, Seq ID No. 21, Seq ID No. 23, Seq ID No. 25 and Seq ID No. 27, B) a sequence that is identical to at least 80%, especially preferably to at least 90%, even more preferably to at least 95% and most preferably to at least 99% to one of the sequences Seq ID No. 1, Seq ID No. 3, Seq ID No. 5, Seq ID No. 7, Seq ID No. 9, Seq ID No.
  • Seq ID No. 11 Seq ID No. 13, Seq ID No. 15, Seq ID No. 17, Seq ID No. 19, Seq ID No. 21, Seq ID No. 23, Seq ID No. 25, Seq ID No. 27, Seq ID No. 29, Seq ID No. 31, Seq ID No. 33, Seq ID No. 35, Seq ID No. 37, Seq ID No. 39, Seq ID No. 41, Seq ID No. 43, Seq ID No. 45, Seq ID No. 47, Seq ID No. 49, Seq ID No. 51, Seq ID No. 53, Seq ID No. 55, Seq ID No. 57, Seq ID No. 59, Seq ID No. 61, Seq ID No. 63, Seq ID No. 65 and Seq ID No.
  • Seq ID No. 67 in particular to Seq ID No. 1, Seq ID No. 3, Seq ID No. 5, Seq ID No. 7, Seq ID No. 9, Seq ID No. 11, Seq ID No. 13, Seq ID No. 15, Seq ID No. 17, Seq ID No. 19, Seq ID No. 21, Seq ID No. 23, Seq ID No. 25, Seq ID No. 27, Seq ID No. 29, Seq ID No. 31, Seq ID No. 33, Seq ID No. 35, Seq ID No. 37, Seq ID No. 39, Seq ID No. 41, Seq ID No. 43, Seq ID No. 45, Seq ID No. 47, Seq ID No. 49 and Seq ID No. 51; quite especially to Seq ID No. 1, Seq ID No. 3, Seq ID No.
  • Seq ID No. 7 Seq ID No. 9, Seq ID No. 11, Seq ID No. 13, Seq ID No. 15, Seq ID No. 17, Seq ID No. 19, Seq ID No. 21, Seq ID No. 23, Seq ID No. 25 and Seq ID No. 27.
  • nucleic acid sequence group that is preferred according to the invention is group A).
  • a “wild type” of a cell preferably means, in connection with the present invention, the starting strain from which the cell according to the invention was derived by manipulation of the elements (for example the genes comprising the aforesaid nucleic acid sequences coding for a corresponding enzyme or the promoters contained in the corresponding gene, which are linked functionally with the aforesaid nucleic acid sequences), which influence the activities of the enzymes encoded by the stated nucleic acid Seq ID No. If for example the activity of the enzyme encoded by Seq ID No. 1 in the strain ATCC 20336 is reduced by interruption of the corresponding gene, then the strain ATCC 20336 that is unchanged and was used for the corresponding manipulation is to be regarded as the “wild type”.
  • gene means, in connection with the present invention, not only the encoding DNA region or that transcribed to mRNA, the “structural gene”, but in addition promoter, possible intron, enhancer and other regulatory sequence, and terminator, regions.
  • activity of an enzyme always means, in connection with the invention, the enzymatic activity that catalyses the reactions of 12-hydroxydodecanoic acid to 1,12-dodecane diacid by the entire cell. This activity is preferably determined by the following method:
  • a 100-ml Erlenmeyer flask with 10 ml of YM medium (0.3% yeast extract, 0.3% malt extract, 0.5% peptone and 1.0% (w/w) glucose) is cultivated at 30° C. and 90 rpm for 24 h.
  • 12-hydroxydodecanoic acid is added to the cell suspension, so that the concentration is not greater than 0.5 g/l.
  • Glucose or glycerol is also added as co-substrate, so that the concentration of the co-substrate does not drop below 0.2 g/l.
  • samples (1 ml) are taken for measurement of 12-hydroxydodecanoic acid, 12-oxo-dodecanoic acid and 1,12-dodecane diacid and the corresponding methyl esters, and for checking the cell count.
  • the pH is kept between 5.0 and 6.5 with 6N NaOH or 4NH 2 SO 4 .
  • cell growth is verified by checking the “colony forming units” (CFU).
  • CFU colony forming units
  • the decrease of 12-hydroxydodecanoic acid and the production of 1,12-dodecane diacid or the corresponding methyl esters are verified by LC-MS.
  • 500 ⁇ l of culture broth is adjusted to pH 1 and then extracted with the same volume of diethyl ether or ethyl acetate and analysed by LC-MS.
  • the measuring system consists of an HP1100 HPLC (Agilent Technologies, Waldbronn, Germany) with degasser, autosampler and column furnace, coupled to a mass-selective quadrupole detector MSD (Agilent Technologies, Waldbronn, Germany). Chromatographic separation is achieved on a reversed phase e.g. 125 ⁇ 2 mm Luna C18(2) column (Phenomenex, Aillesburg, Germany) at 40° C. Gradient elution is performed at a flow of 0.3 ml/min (A: 0.02% formic acid in water and B: 0.02% formic acid in acetonitrile).
  • the organic extracts are analysed by GC-FID (Perkin Elmer, Rodgau-Jügesheim, Germany). Chromatographic separation is performed on a methylpolysiloxane (5% phenyl) phase e.g. Elite 5, 30 m, 0.25 mm ID, 0.25 ⁇ m FD (Perkin Elmer, Rodgau-Jügesheim, Germany). Before measurement, a methylation reagent e.g. trimethylsulphonium hydroxide “TMSH” (Macherey-Nagel GmbH & Co. KG, Düren, Germany) is added to free acids and on injection they are converted to the corresponding methyl esters.
  • TMSH trimethylsulphonium hydroxide
  • the formulation “reduced activity compared with its wild type” means an activity relative to the wild-type activity preferably reduced by at least 50%, especially preferably by at least 90%, more preferably by at least 99.9%, even more preferably by at least 99.99% and most preferably by at least 99.999%.
  • the decrease in activity of the cell according to the invention compared with its wild type is determined by the method described above for determining activity using cell numbers/concentrations as identical as possible, the cells having been grown under the same conditions, for example medium, gassing, agitation.
  • Nucleotide identity relative to the stated sequences can be determined using known methods. Generally, special computer programs are used with algorithms taking special requirements into account. Preferred methods for determining identity first produce the greatest agreement between the sequences to be compared. Computer programs for determining identity comprise, but are not restricted to, the GCG software package, including
  • the known Smith-Waterman algorithm can also be used for determining nucleotide identity.
  • nucleotide identity is, when using the BLASTN program (Altschul, S. et al., Journal of Molecular Biology 215 (1990), pages 403-410):
  • the above parameters are the default parameters in nucleotide sequence comparison.
  • the GAP program is also suitable for use with the above parameters.
  • An identity of 80% according to the above algorithm means, in connection with the present invention, 80% identity. The same applies to higher identities.
  • Cells preferred according to the invention are characterized in that the decrease in enzymatic activity is achieved by modification of at least one gene comprising one of the sequences selected from the previously stated nucleic acid sequence groups A) and B), the modification being selected from the group comprising, preferably consisting of, insertion of foreign DNA into the gene, deletion at least of parts of the gene, point mutations in the gene sequence and subjecting the gene to the influence of RNA interference or exchange of parts of the gene with foreign DNA, in particular of the promoter region.
  • Foreign DNA means, in this context, any DNA sequence that is “foreign” to the gene (and not to the organism), i.e. even Candida tropicalis endogenous DNA sequences can, in this context, function as “foreign DNA”.
  • the gene is interrupted by insertion of a selection marker gene, therefore the foreign DNA is a selection marker gene, the insertion preferably having been effected by homologous recombination into the gene locus.
  • the selection marker gene is expanded with further functionalities, which in their turn make subsequent removal from the gene possible, this can be achieved for example with a Cre/loxP system, with Flippase Recognition Targets (FRT) or by homologous recombination.
  • FRT Flippase Recognition Targets
  • Cells preferred according to the invention are characterized in that they are blocked in their ⁇ -oxidation at least partially, preferably completely, as this prevents outflow of substrate and therefore higher titres become possible.
  • Candida tropicalis cells partially blocked in their ⁇ -oxidation are described in EP0499622 as strains H41, H41B, H51, H45, H43, H53, H534, H534B and H435, from which a Candida tropicalis cell preferred according to the invention is derived.
  • Candida tropicalis cells blocked for ⁇ -oxidation are described for example in WO03/100013.
  • cells are preferred for which the ⁇ -oxidation is caused by an induced malfunction of at least one of the genes POX2, POX4 or POX5.
  • a Candida tropicalis cell preferred according to the invention is derived from strains selected from the group comprising ATCC 20962 and the Candida tropicalis HDC100 described in US2004/0014198.
  • the use of the cells according to the invention for the production of ⁇ -hydroxycarboxylic acids or ⁇ -hydroxycarboxylic acid esters with a chain length of the carboxylic acid from 6 to 24, preferably 8 to 18 and especially preferably 10 to 16 carbon atoms, which are preferably linear, saturated and unsubstituted, and a chain length of the alcohol component of the ester from 1 to 4, in particular 1 or 2 carbon atoms, is advantageous.
  • the ⁇ -hydroxycarboxylic acids it is preferable for the ⁇ -hydroxycarboxylic acids to be 12-hydroxydodecanoic acid and for the ⁇ -hydroxycarboxylic acid ester to be 12-hydroxydodecanoic acid methyl ester.
  • a preferred use is characterized according to the invention in that preferred cells according to the invention as described above are used.
  • a C. tropicalis cell preferably a cell that is blocked in its ⁇ -oxidation at least partially, preferably completely
  • Modification of at least one gene comprising one of the intron-free nucleic acid sequences selected from the previously stated nucleic acid sequence groups A) and B) by insertion of foreign DNA, in particular of DNA coding for a selection marker gene, into the gene, deletion of at least parts of the gene, point mutations in the gene sequence and subjecting the gene to the influence of RNA interference or exchange of parts of the gene with foreign DNA, in particular of the promoter region.
  • ⁇ -hydroxycarboxylic acids or ⁇ -hydroxycarboxylic acid esters in particular of ⁇ -hydroxycarboxylic acids or ⁇ -hydroxycarboxylic acid esters with a chain length of the carboxylic acid from 6 to 24, preferably 8 to 18 and especially preferably 10 to 16 carbon atoms, which are preferably linear, saturated and unsubstituted, and a chain length of the alcohol component of the ester from 1 to 4, in particular of 1 or 2 carbon atoms, in particular of 12-hydroxydodecanoic acid or 12-hydroxydodecanoic acid methyl ester comprising the steps
  • a medium comprising a carboxylic acid or a carboxylic acid ester, in particular a carb
  • Suitable cultivation conditions for Candida tropicalis are known by a person skilled in the art.
  • suitable conditions for step b) are those that are known by a person skilled in the art from bioconversion methods of production of dicarboxylic acids with Candida tropicalis.
  • ⁇ -hydroxycarboxylic acids or ⁇ -hydroxycarboxylic acid esters obtained by the method according to the invention for the production of polymers, in particular polyesters.
  • lactones can also be produced from the ⁇ -hydroxy carboxylic acids, and can then for example be used in their turn for the production of polyesters.
  • Another advantageous use is to convert the ⁇ -hydroxycarboxylic acids or ⁇ -hydroxycarboxylic acid esters to ⁇ -aminocarboxylic acids or ⁇ -aminocarboxylic acid esters, in order to obtain polyamides as polymers.
  • the ⁇ -aminocarboxylic acids or ⁇ -aminocarboxylic acid esters can also be converted first to the corresponding lactams, which can then in their turn be converted using anionic, or also acid catalysis to a polyamide.
  • 12-hydroxy dodecanoic acid or 12-hydroxydodecanoic acid methyl ester for the production of polymers, in particular of polyamide 12, is especially preferred.

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US9909151B2 (en) 2012-12-19 2018-03-06 Verdezyne, Inc. Biological methods for preparing a fatty dicarboxylic acid
US9850493B2 (en) 2012-12-19 2017-12-26 Verdezyne, Inc. Biological methods for preparing a fatty dicarboxylic acid
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US9695404B2 (en) 2014-07-18 2017-07-04 Industrial Technology Research Institute Genetically modified microorganism for producing long-chain dicarboxylic acid and method of using thereof
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