EP4673552A1 - Verfahren zur herstellung von l-pipecolinsäure - Google Patents

Verfahren zur herstellung von l-pipecolinsäure

Info

Publication number
EP4673552A1
EP4673552A1 EP24713679.9A EP24713679A EP4673552A1 EP 4673552 A1 EP4673552 A1 EP 4673552A1 EP 24713679 A EP24713679 A EP 24713679A EP 4673552 A1 EP4673552 A1 EP 4673552A1
Authority
EP
European Patent Office
Prior art keywords
lysin
acid
pip
xpr
colic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP24713679.9A
Other languages
English (en)
French (fr)
Inventor
Christoph Wittmann
Sarah PAULI
Michael Kohlstedt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Universitaet des Saarlandes
Original Assignee
Universitaet des Saarlandes
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Universitaet des Saarlandes filed Critical Universitaet des Saarlandes
Publication of EP4673552A1 publication Critical patent/EP4673552A1/de
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C12P13/005—Amino acids other than alpha- or beta amino acids, e.g. gamma amino acids
    • 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
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
    • C12N15/74—Vectors or expression systems specially adapted for prokaryotic hosts other than E. coli, e.g. Lactobacillus, Micromonospora
    • C12N15/77—Vectors or expression systems specially adapted for prokaryotic hosts other than E. coli, e.g. Lactobacillus, Micromonospora for Corynebacterium; for Brevibacterium
    • 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)
    • C12N9/0026—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7) acting on CH-NH groups of donors (1.5)
    • C12N9/0028—Oxidoreductases (1.) acting on nitrogen containing compounds as donors (1.4, 1.5, 1.6, 1.7) acting on CH-NH groups of donors (1.5) with NAD or NADP as acceptor (1.5.1)
    • 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
    • C12N9/10—Transferases (2.)
    • C12N9/1096—Transferases (2.) transferring nitrogenous groups (2.6)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y105/00—Oxidoreductases acting on the CH-NH group of donors (1.5)
    • C12Y105/01—Oxidoreductases acting on the CH-NH group of donors (1.5) with NAD+ or NADP+ as acceptor (1.5.1)
    • C12Y105/01002—Pyrroline-5-carboxylate reductase (1.5.1.2)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y206/00—Transferases transferring nitrogenous groups (2.6)
    • C12Y206/01—Transaminases (2.6.1)
    • C12Y206/01036—L-Lysine 6-transaminase (2.6.1.36)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • C12R2001/15—Corynebacterium

Definitions

  • ⁇ ⁇ omm ⁇ rcial ⁇ us ⁇ of ⁇ L ⁇ pip ⁇ colic ⁇ acid, ⁇ ⁇ .g. ⁇ in ⁇ th ⁇ pharmac ⁇ utical ⁇ ar ⁇ a, ⁇ food ⁇ industry ⁇ or ⁇ cosm ⁇ tics, ⁇ r ⁇ quir ⁇ s ⁇ a ⁇ high ⁇ optical ⁇ purity ⁇ (Madd ⁇ ss ⁇ t ⁇ al., ⁇ rog ⁇ Drug ⁇ R ⁇ s ⁇ (2008) ⁇ 66: ⁇ 15 ⁇ 186).
  • Whil ⁇ ch ⁇ mical ⁇ synth ⁇ sis ⁇ m ⁇ thods ⁇ can ⁇ b ⁇ us ⁇ d ⁇ to ⁇ yi ⁇ ld ⁇ larg ⁇ amounts ⁇ of ⁇ pip ⁇ colic ⁇ acid, ⁇ s ⁇ l ⁇ ction ⁇ of ⁇ prop ⁇ r ⁇ rac ⁇ mat ⁇ s ⁇ among ⁇ D ⁇ and ⁇ L ⁇ pip ⁇ colic ⁇ acid ⁇ isom ⁇ rs ⁇ is ⁇ cost ⁇ and ⁇ tim ⁇ int ⁇ ns ⁇ , ⁇ making ⁇ L ⁇ pip ⁇ colic ⁇ acid ⁇ v ⁇ ry ⁇ ⁇ xp ⁇ n
  • “D ⁇ viations” ⁇ from ⁇ s ⁇ qu ⁇ nc ⁇ s ⁇ ( ⁇ .g., ⁇ amino ⁇ acid ⁇ or ⁇ nucl ⁇ ic ⁇ acid ⁇ s ⁇ qu ⁇ nc ⁇ s) ⁇ as ⁇ us ⁇ d ⁇ h ⁇ r ⁇ in ⁇ may ⁇ compris ⁇ , ⁇ ⁇ .g., ⁇ d ⁇ l ⁇ tions, ⁇ substitutions, ⁇ additions, ⁇ ins ⁇ rtion ⁇ and/or ⁇ r ⁇ combination. ⁇ ⁇ h ⁇ t ⁇ rm ⁇ "addition” r ⁇ f ⁇ rs ⁇ to ⁇ adding ⁇ a ⁇ nucl ⁇ ic ⁇ acid ⁇ r ⁇ sidu ⁇ /amino ⁇ acid ⁇ to ⁇ th ⁇ nd ⁇ or ⁇ b ⁇ ginning ⁇ of ⁇ th ⁇ giv ⁇ n ⁇ s ⁇ qu ⁇ nc ⁇ , ⁇ h ⁇ r ⁇ as ⁇ "ins ⁇ rtion” ⁇ r ⁇ f ⁇ rs to ⁇ ins ⁇ rting ⁇ a ⁇ nucl ⁇ ic ⁇ acid ⁇ r ⁇ sidu ⁇ /amino ⁇ acid ⁇ ⁇ it
  • ⁇ h ⁇ r ⁇ sp ⁇ ctiv ⁇ c ⁇ ll ⁇ ⁇ hich ⁇ is ⁇ “g ⁇ n ⁇ tically ⁇ ⁇ ngin ⁇ r ⁇ d” ⁇ in ⁇ accordanc ⁇ ⁇ ith ⁇ this ⁇ inv ⁇ ntion ⁇ may ⁇ contain ⁇ th ⁇ introduc ⁇ d ⁇ polynucl ⁇ otid ⁇ ⁇ ith ⁇ r ⁇ on ⁇ an ⁇ ⁇ xtrachromosomal ⁇ mol ⁇ cul ⁇ ( ⁇ .g., ⁇ on ⁇ a ⁇ plasmid) ⁇ or ⁇ th ⁇ polynucl ⁇ otid ⁇ may ⁇ b ⁇ (stably) ⁇ int ⁇ grat ⁇ d ⁇ into ⁇ th ⁇ or ⁇ a ⁇ c ⁇ ll ⁇ chromosom ⁇ .
  • ⁇ h ⁇ introduc ⁇ d ⁇ polynucl ⁇ otid ⁇ may ⁇ stand ⁇ und ⁇ r ⁇ th ⁇ control ⁇ of ⁇ its ⁇ o ⁇ n ⁇ promot ⁇ r or ⁇ r ⁇ gulator ⁇ or ⁇ th ⁇ lik ⁇ (introduc ⁇ d ⁇ tog ⁇
  • nucl ⁇ ic ⁇ acid ⁇ mol ⁇ cul ⁇ s ⁇ may ⁇ compris ⁇ ⁇ n ⁇ er ⁇ a ⁇ a D ⁇ A ⁇ mol ⁇ cul ⁇ s, ⁇ R ⁇ A ⁇ mol ⁇ cul ⁇ s, ⁇ oligonucl ⁇ otid ⁇ thiophosphat ⁇ s, ⁇ substitut ⁇ d ⁇ ribo ⁇ oligonucl ⁇ otid ⁇ s ⁇ or ⁇ ⁇ A ⁇ mol ⁇ cul ⁇ s.
  • ⁇ th ⁇ g ⁇ n ⁇ s ⁇ for ⁇ pyrrolin ⁇ 5 ⁇ carboxylat ⁇ r ⁇ ductas ⁇ and/or ⁇ lysin ⁇ 6 ⁇ aminotransf ⁇ ras ⁇ may ⁇ b ⁇ ⁇ xpr ⁇ ss ⁇ d ⁇ on ⁇ s ⁇ parat ⁇ or ⁇ th ⁇ sam ⁇ op ⁇ ron, ⁇ r ⁇ gardl ⁇ ss ⁇ ⁇ h ⁇ th ⁇ r ⁇ said ⁇ g ⁇ n ⁇ (s) ⁇ is ⁇ (ar ⁇ ) ⁇ pr ⁇ s ⁇ nt ⁇ in ⁇ th ⁇ host ⁇ c ⁇ ll ⁇ as ⁇ naturally ⁇ contain ⁇ d ⁇ g ⁇ n ⁇ (s) ⁇ or ⁇ introduc ⁇ d ⁇ (i. ⁇ . ⁇ c ⁇ lls ⁇ ar ⁇ g ⁇ n ⁇ tically ⁇ ngin ⁇ r ⁇ d ⁇ to ⁇ contain ⁇ such ⁇ g ⁇ n ⁇ (s)).
  • ⁇ th ⁇ polynucl ⁇ otid ⁇ s ⁇ ⁇ ncoding ⁇ pyrrolin ⁇ 5 ⁇ carboxylat ⁇ r ⁇ ductas ⁇ and/or ⁇ lysin ⁇ 6 ⁇ aminotransf ⁇ ras ⁇ may ⁇ stand ⁇ und ⁇ r ⁇ th ⁇ control ⁇ of ⁇ a ⁇ constitutiv ⁇ or ⁇ r ⁇ gulat ⁇ d ⁇ promot ⁇ r. ⁇ ⁇ r ⁇ f ⁇ rably, ⁇ th ⁇ polynucl ⁇ otid ⁇ s ⁇ ⁇ ncoding ⁇ pyrrolin ⁇ 5 ⁇ carboxylat ⁇ r ⁇ ductas ⁇ and/or ⁇ lysin ⁇ 6 ⁇ aminotransf ⁇ ras ⁇ ar ⁇ und ⁇ r ⁇ th ⁇ control ⁇ of ⁇ a ⁇ constitutiv ⁇ promot ⁇ r. ⁇ Mor ⁇ pr ⁇ f ⁇ rably, ⁇ th ⁇ polynucl ⁇ otid ⁇ s ⁇ ncoding
  • a ⁇ bact ⁇ rial ⁇ host ⁇ c ⁇ ll ⁇ b ⁇ ing ⁇ g ⁇ n ⁇ tically ⁇ ngin ⁇ r ⁇ d ⁇ to ⁇ xpr ⁇ ss ⁇ in ⁇ on ⁇ op ⁇ ron ⁇ lysin ⁇ 6 ⁇ aminotransf ⁇ ras ⁇ and ⁇ pyrrolin ⁇ 5 ⁇ carboxylat ⁇ r ⁇ ductas ⁇ is ⁇ und ⁇ r ⁇ th ⁇ control ⁇ of ⁇ th ⁇ tuf ⁇ promot ⁇ r, ⁇ pr ⁇ f ⁇ rably ⁇ th ⁇ tuf ⁇ promot ⁇ r ⁇ sho ⁇ n ⁇ in ⁇ SEQ ⁇ ID ⁇ O: ⁇ 1 ⁇ or ⁇ und ⁇ r ⁇ th ⁇ control ⁇ of ⁇ th ⁇ sod ⁇ promot ⁇ r, ⁇ pr ⁇ f ⁇ rably ⁇ th ⁇ sod ⁇ promot ⁇ r sho ⁇ n ⁇ SEQ ⁇ ID ⁇ os: ⁇ 2 ⁇ or ⁇ 3, and ⁇ b ⁇ ing furth ⁇ r ⁇ charact ⁇ riz ⁇ d ⁇ by ⁇ ov ⁇ rproduction ⁇ of ⁇ lysin ⁇ .
  • G ⁇ nom ⁇ bas ⁇ d ⁇ xpr ⁇ ssion ⁇ of ⁇ g ⁇ n ⁇ s ⁇ of ⁇ int ⁇ r ⁇ st ⁇ for ⁇ improv ⁇ d ⁇ r ⁇ dox ⁇ supply ⁇ including ⁇ th ⁇ nativ ⁇ transhydrog ⁇ nas ⁇ g ⁇ n ⁇ pn ⁇ AB from ⁇ E ⁇ ⁇ K12 ⁇ MG1655 ⁇ (Hoffmann ⁇ ⁇ t ⁇ al., ⁇ 2021, ⁇ ⁇ ⁇ ⁇ .) and ⁇ a ⁇ codon ⁇ optimiz ⁇ d ⁇ v ⁇ rsion ⁇ of ⁇ gapN from ⁇ ⁇ rep ⁇ us ⁇ mu ⁇ ans UA159, ⁇ ⁇ ncoding ⁇ ⁇ AD ⁇ d ⁇ p ⁇ nd ⁇ nt ⁇ glyc ⁇ rald ⁇ hyd ⁇ 3 ⁇ phosphat ⁇ d ⁇ hydrog ⁇ nas ⁇ (Hoffmann ⁇ t ⁇ al., ⁇ 2018, ⁇ ⁇ ⁇ .), ⁇ as ⁇ bas ⁇ d ⁇ on ⁇ th ⁇ int ⁇ grativ ⁇ v ⁇ ctor ⁇ pC ⁇ k ⁇ n ⁇ sa ⁇ B.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Biomedical Technology (AREA)
  • Microbiology (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Plant Pathology (AREA)
  • Biophysics (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Data Exchanges In Wide-Area Networks (AREA)
EP24713679.9A 2023-03-02 2024-03-01 Verfahren zur herstellung von l-pipecolinsäure Pending EP4673552A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP23159532 2023-03-02
PCT/EP2024/055384 WO2024180222A1 (en) 2023-03-02 2024-03-01 Methods for producing l-pipecolic acid

Publications (1)

Publication Number Publication Date
EP4673552A1 true EP4673552A1 (de) 2026-01-07

Family

ID=85415379

Family Applications (1)

Application Number Title Priority Date Filing Date
EP24713679.9A Pending EP4673552A1 (de) 2023-03-02 2024-03-01 Verfahren zur herstellung von l-pipecolinsäure

Country Status (2)

Country Link
EP (1) EP4673552A1 (de)
WO (1) WO2024180222A1 (de)

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4711955A (en) 1981-04-17 1987-12-08 Yale University Modified nucleotides and methods of preparing and using same
CA1223831A (en) 1982-06-23 1987-07-07 Dean Engelhardt Modified nucleotides, methods of preparing and utilizing and compositions containing the same
US4683195A (en) 1986-01-30 1987-07-28 Cetus Corporation Process for amplifying, detecting, and/or-cloning nucleic acid sequences
US5792608A (en) 1991-12-12 1998-08-11 Gilead Sciences, Inc. Nuclease stable and binding competent oligomers and methods for their use
US5525711A (en) 1994-05-18 1996-06-11 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Pteridine nucleotide analogs as fluorescent DNA probes
RU2535973C2 (ru) 2010-06-15 2014-12-20 Пайк Кванг Индастриал Ко., Лтд. Способ продуцирования аминокислот семейства аспартата с использованием микроорганизмов
CN104395466A (zh) 2012-06-13 2015-03-04 日本迈科洛生物制药有限公司 顺式-5-羟基-l-六氢吡啶甲酸的生物学制备方法
BR112014030845A2 (pt) 2012-07-11 2017-06-27 Halliburton Energy Services Inc sistema de fresagem para formar uma saída de revestimento, e, método para controlar aparas e detritos.
US20180282768A1 (en) 2015-08-28 2018-10-04 Universitaet Des Saarlandes Means and methods for production of organic compounds

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Publication number Publication date
WO2024180222A1 (en) 2024-09-06

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