DK2970872T1 - Mikroorganismer og fremgangsmåder til fremstilling af sialylerede og N-acetylglucosamin-holdige oligosaccharider - Google Patents
Mikroorganismer og fremgangsmåder til fremstilling af sialylerede og N-acetylglucosamin-holdige oligosaccharider Download PDFInfo
- Publication number
- DK2970872T1 DK2970872T1 DK14769797.3T DK14769797T DK2970872T1 DK 2970872 T1 DK2970872 T1 DK 2970872T1 DK 14769797 T DK14769797 T DK 14769797T DK 2970872 T1 DK2970872 T1 DK 2970872T1
- Authority
- DK
- Denmark
- Prior art keywords
- gene
- bacterium
- endogenous
- gicnac
- udp
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 40
- 229920001542 oligosaccharide Polymers 0.000 title claims 15
- 150000002482 oligosaccharides Chemical class 0.000 title claims 15
- 244000005700 microbiome Species 0.000 title 1
- 241000894006 Bacteria Species 0.000 claims 22
- 238000004519 manufacturing process Methods 0.000 claims 13
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims 11
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 claims 11
- 101150006297 nagC gene Proteins 0.000 claims 10
- 108090000623 proteins and genes Proteins 0.000 claims 10
- 108010005774 beta-Galactosidase Proteins 0.000 claims 8
- 230000035772 mutation Effects 0.000 claims 8
- 241000588724 Escherichia coli Species 0.000 claims 7
- 230000015556 catabolic process Effects 0.000 claims 7
- 230000002950 deficient Effects 0.000 claims 7
- 230000001580 bacterial effect Effects 0.000 claims 6
- 108010060845 lactose permease Proteins 0.000 claims 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 5
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims 5
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims 5
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 claims 5
- 108090000141 Sialyltransferases Proteins 0.000 claims 5
- 239000008101 lactose Substances 0.000 claims 5
- 229950006780 n-acetylglucosamine Drugs 0.000 claims 5
- 108700026220 vif Genes Proteins 0.000 claims 5
- 108090001066 Racemases and epimerases Proteins 0.000 claims 4
- 239000012228 culture supernatant Substances 0.000 claims 4
- 101150117187 glmS gene Proteins 0.000 claims 4
- 102000048245 N-acetylneuraminate lyases Human genes 0.000 claims 3
- 108700023220 N-acetylneuraminate lyases Proteins 0.000 claims 3
- 229910019142 PO4 Inorganic materials 0.000 claims 3
- 108091000080 Phosphotransferase Proteins 0.000 claims 3
- LFTYTUAZOPRMMI-CFRASDGPSA-N UDP-N-acetyl-alpha-D-glucosamine Chemical compound O1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](NC(=O)C)[C@H]1OP(O)(=O)OP(O)(=O)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(NC(=O)C=C2)=O)O1 LFTYTUAZOPRMMI-CFRASDGPSA-N 0.000 claims 3
- LFTYTUAZOPRMMI-UHFFFAOYSA-N UNPD164450 Natural products O1C(CO)C(O)C(O)C(NC(=O)C)C1OP(O)(=O)OP(O)(=O)OCC1C(O)C(O)C(N2C(NC(=O)C=C2)=O)O1 LFTYTUAZOPRMMI-UHFFFAOYSA-N 0.000 claims 3
- 102000005936 beta-Galactosidase Human genes 0.000 claims 3
- 101150076570 nanK gene Proteins 0.000 claims 3
- 108020004707 nucleic acids Proteins 0.000 claims 3
- 150000007523 nucleic acids Chemical class 0.000 claims 3
- 102000039446 nucleic acids Human genes 0.000 claims 3
- 239000010452 phosphate Substances 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 101710150619 Sialic acid TRAP transporter permease protein SiaT Proteins 0.000 claims 2
- 102000003838 Sialyltransferases Human genes 0.000 claims 2
- AXQLFFDZXPOFPO-UHFFFAOYSA-N UNPD216 Natural products O1C(CO)C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(=O)C)C1OC(C1O)C(O)C(CO)OC1OC1C(O)C(O)C(O)OC1CO AXQLFFDZXPOFPO-UHFFFAOYSA-N 0.000 claims 2
- AXQLFFDZXPOFPO-UNTPKZLMSA-N beta-D-Galp-(1->3)-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-beta-D-Glcp Chemical compound O([C@@H]1O[C@H](CO)[C@H](O)[C@@H]([C@H]1O)O[C@H]1[C@@H]([C@H]([C@H](O)[C@@H](CO)O1)O[C@H]1[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O1)O)NC(=O)C)[C@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@@H]1CO AXQLFFDZXPOFPO-UNTPKZLMSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 238000004113 cell culture Methods 0.000 claims 2
- 239000013592 cell lysate Substances 0.000 claims 2
- 238000012258 culturing Methods 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- IEQCXFNWPAHHQR-UHFFFAOYSA-N lacto-N-neotetraose Natural products OCC1OC(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)C(NC(=O)C)C(O)C1OC1OC(CO)C(O)C(O)C1O IEQCXFNWPAHHQR-UHFFFAOYSA-N 0.000 claims 2
- USIPEGYTBGEPJN-UHFFFAOYSA-N lacto-N-tetraose Natural products O1C(CO)C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(=O)C)C1OC1C(O)C(CO)OC(OC(C(O)CO)C(O)C(O)C=O)C1O USIPEGYTBGEPJN-UHFFFAOYSA-N 0.000 claims 2
- 229940062780 lacto-n-neotetraose Drugs 0.000 claims 2
- RBMYDHMFFAVMMM-PLQWBNBWSA-N neolactotetraose Chemical compound O([C@H]1[C@H](O)[C@H]([C@@H](O[C@@H]1CO)O[C@@H]1[C@H]([C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@H](CO)[C@@H]1O)O)NC(=O)C)[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O RBMYDHMFFAVMMM-PLQWBNBWSA-N 0.000 claims 2
- 102000020233 phosphotransferase Human genes 0.000 claims 2
- 101100245749 Campylobacter jejuni subsp. jejuni serotype O:23/36 (strain 81-176) pseF gene Proteins 0.000 claims 1
- 108010078791 Carrier Proteins Proteins 0.000 claims 1
- 101100186924 Escherichia coli neuC gene Proteins 0.000 claims 1
- 101000588377 Homo sapiens N-acylneuraminate cytidylyltransferase Proteins 0.000 claims 1
- TVVLIFCVJJSLBL-SEHWTJTBSA-N Lacto-N-fucopentaose V Chemical compound O[C@H]1C(O)C(O)[C@H](C)O[C@H]1OC([C@@H](O)C=O)[C@@H](C(O)CO)O[C@H]1[C@H](O)[C@@H](OC2[C@@H](C(OC3[C@@H](C(O)C(O)[C@@H](CO)O3)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@@H](CO)O1 TVVLIFCVJJSLBL-SEHWTJTBSA-N 0.000 claims 1
- ZHYLZEPTSHTOHM-UHFFFAOYSA-N Lacto-N-neo-difucohexaose II Natural products CC1OC(OC2C(O)C(O)OC(CO)C2OC3OC(CO)C(O)C(OC4OC(CO)C(OC5OC(CO)C(O)C(O)C5O)C(OC6OC(C)C(O)C(O)C6O)C4NC(=O)C)C3O)C(O)C(O)C1O ZHYLZEPTSHTOHM-UHFFFAOYSA-N 0.000 claims 1
- 101100186921 Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513) neuB gene Proteins 0.000 claims 1
- DUKURNFHYQXCJG-UHFFFAOYSA-N Lewis A pentasaccharide Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(C)=O)C(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)OC1CO DUKURNFHYQXCJG-UHFFFAOYSA-N 0.000 claims 1
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 claims 1
- 108010035265 N-acetylneuraminate synthase Proteins 0.000 claims 1
- 102000004879 Racemases and epimerases Human genes 0.000 claims 1
- 102000004357 Transferases Human genes 0.000 claims 1
- 108090000992 Transferases Proteins 0.000 claims 1
- 108020002494 acetyltransferase Proteins 0.000 claims 1
- FZIVHOUANIQOMU-YIHIYSSUSA-N alpha-L-Fucp-(1->2)-beta-D-Galp-(1->3)-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-D-Glcp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@@H]2[C@H]([C@H](O[C@@H]3[C@H]([C@H](O[C@@H]4[C@H](OC(O)[C@H](O)[C@H]4O)CO)O[C@H](CO)[C@@H]3O)O)O[C@H](CO)[C@H]2O)NC(C)=O)O[C@H](CO)[C@H](O)[C@@H]1O FZIVHOUANIQOMU-YIHIYSSUSA-N 0.000 claims 1
- RQNFGIWYOACERD-OCQMRBNYSA-N alpha-L-Fucp-(1->4)-[alpha-L-Fucp-(1->2)-beta-D-Galp-(1->3)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-D-Glcp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](CO)O[C@@H](O[C@@H]3[C@H]([C@H](O[C@@H]4[C@H](OC(O)[C@H](O)[C@H]4O)CO)O[C@H](CO)[C@@H]3O)O)[C@@H]2NC(C)=O)O[C@H]2[C@H]([C@H](O)[C@H](O)[C@H](C)O2)O)O[C@H](CO)[C@H](O)[C@@H]1O RQNFGIWYOACERD-OCQMRBNYSA-N 0.000 claims 1
- DMYPRRDPOMGEAK-XWDFSUOISA-N beta-D-Galp-(1->3)-[alpha-L-Fucp-(1->4)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-D-Glcp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O[C@H]4[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O4)O)[C@H](O[C@H]4[C@H]([C@H](O)[C@H](O)[C@H](C)O4)O)[C@@H](CO)O3)NC(C)=O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)OC(O)[C@@H]1O DMYPRRDPOMGEAK-XWDFSUOISA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 101150086432 lacA gene Proteins 0.000 claims 1
- 101150066555 lacZ gene Proteins 0.000 claims 1
- RQNFGIWYOACERD-UHFFFAOYSA-N lacto-N-Difucosylhexaose I Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(CO)OC(OC3C(C(OC4C(OC(O)C(O)C4O)CO)OC(CO)C3O)O)C2NC(C)=O)OC2C(C(O)C(O)C(C)O2)O)OC(CO)C(O)C1O RQNFGIWYOACERD-UHFFFAOYSA-N 0.000 claims 1
- OQIUPKPUOLIHHS-UHFFFAOYSA-N lacto-N-difucohexaose I Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(CO)OC(OC3C(C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C3O)O)C2NC(C)=O)OC2C(C(O)C(O)C(C)O2)O)OC(CO)C(O)C1O OQIUPKPUOLIHHS-UHFFFAOYSA-N 0.000 claims 1
- DMYPRRDPOMGEAK-UHFFFAOYSA-N lacto-N-difucohexaose II Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(OC3C(C(OC4C(C(O)C(O)C(CO)O4)O)C(OC4C(C(O)C(O)C(C)O4)O)C(CO)O3)NC(C)=O)C(O)C(CO)O2)O)C(CO)OC(O)C1O DMYPRRDPOMGEAK-UHFFFAOYSA-N 0.000 claims 1
- FZIVHOUANIQOMU-UHFFFAOYSA-N lacto-N-fucopentaose I Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(OC3C(C(OC4C(OC(O)C(O)C4O)CO)OC(CO)C3O)O)OC(CO)C2O)NC(C)=O)OC(CO)C(O)C1O FZIVHOUANIQOMU-UHFFFAOYSA-N 0.000 claims 1
- CMQZRJBJDCVIEY-UHFFFAOYSA-N lacto-N-fucopentaose III Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(CO)OC(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)C1NC(C)=O CMQZRJBJDCVIEY-UHFFFAOYSA-N 0.000 claims 1
- RJTOFDPWCJDYFZ-UHFFFAOYSA-N lacto-N-triose Natural products CC(=O)NC1C(O)C(O)C(CO)OC1OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1O RJTOFDPWCJDYFZ-UHFFFAOYSA-N 0.000 claims 1
- 101150019075 neuA gene Proteins 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/02—Monosaccharides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/195—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria
- C07K14/24—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria from Enterobacteriaceae (F), e.g. Citrobacter, Serratia, Proteus, Providencia, Morganella, Yersinia
- C07K14/245—Escherichia (G)
-
- 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
- C12N15/11—DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
- C12N15/52—Genes encoding for enzymes or proenzymes
-
- 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.)
- C12N9/1048—Glycosyltransferases (2.4)
- C12N9/1051—Hexosyltransferases (2.4.1)
-
- 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.)
- C12N9/1048—Glycosyltransferases (2.4)
- C12N9/1081—Glycosyltransferases (2.4) transferring other glycosyl groups (2.4.99)
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Plant Pathology (AREA)
- Physics & Mathematics (AREA)
- Gastroenterology & Hepatology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Claims (43)
1. Fremgangsmåde til fremstilling af et sialyleret oligosaccharid i en bakterie omfattende: tilvejebringelse af en bakterie, hvilken bakterie omfatter en exogen sialyltransferase, en deficient sialinsyre katabolisk proces, en sialinsyre syntetisk kapabilitet, og et funktionelt lactosepermeasegen; og dyrkning af bakterien under tilstedeværelse af lactose.
2. Fremgangsmåde ifølge krav 1, hvor den deficiente sialinsyre kataboliske proces omfatter en mutation i et vilkårligt af generne valgt fra endogen N-acetylneuraminat-lyase {nariA)-gen, endogent N-acetylmannoseaminkinasegen (nanK), endogent N-acetylmannoseamin-6-phosphatepimerasegen (nanE), og endogent N-acetylneuramin-syretransportergen (nanT), eller en vilkårlig kombination deraf.
3. Fremgangsmåde ifølge krav 1, hvor den deficiente sialinsyre kataboliske proces omfatter en mutation i endogent N-acetylneuraminat-lyase (nanA)-gen, og eventuelt, en mutation i endogent N-acetylneuraminsyretransportergen {nanT).
4. Fremgangsmåde ifølge krav 2, hvor den deficiente sialinsyre kataboliske proces yderligere omfatter et endogent N-acetylmannoseaminkinasegen (nanK) og endogent N-acetylmannoseamin-6-phosphatepimerasegen {nanE), som ikke er muterede.
5. Fremgangsmåde ifølge krav 1, hvor den deficiente sialinsyre kataboliske proces omfatter en mutation i endogent N-acetylneuraminat-lyase {nanA)-gen, en mutation i endogent N-acetylmannoseamin-6-phosphatepimerasegen {nanE), og eventuelt en mutation i endogent N-acetylneuraminsyretransportergen {nanT).
6. Fremgagnsmåde ifølge ethvert af de foregående krav, hvor mutationen omfatter en null-mutation.
7. Fremgangsmåde ifølge krav 5, hvor den deficiente sialinsyre kataboliske proces yderligere omfatter et endogent N-acetylmannoseaminkinasegen {nanK), som ikke er muteret.
8. Fremgangsmåde ifølge ethvert af de foregående krav, hvor den sialinsyresyntetiske kapabilitet omfatter et exogent CMP-Neu5Ac-syntetasegen (neuA), et exogent sialinsyresyntasegen (neuB), og en exogen UDP-GIcNac 2-epimerase (neuC).
9. Fremgangsmåde ifølge ethvert af de foregående krav, hvor det exogene sialyl-transferasegen er a(2,3)-sialyltransferase, a(2,6)-sialyltransferase eller a(2,8-sialyl-transferase.
10. Fremgangsmåde ifølge ethvert af de foregående krav, hvor det sialylerede oligosaccharid omfatter 3’-sialinlactose (3’-SL) eller 6’-sialinlactose (6’-SL).
11. Fremgangsmåde ifølge ethvert af de foregående krav, hvor bakterien omfatter et fjernet eller inaktiveret endogent β-galactosidasegen.
12. Fremgangsmåde ifølge krav 11, hvor det fjernede eller inaktiverede β-galactosidase-gen omfatter E. coli lacZ-gen.
13. Fremgangsmåde ifølge krav 1, hvor bakterien omfatter et rekombinant β-galactosidasegen, som tilvejebringer et lavt men detekterbart niveau af β-galactosidase-aktivitet.
14. Fremgangsmåde ifølge ethvert af de foregående krav, hvor bakterien yderligere omfatter et fjernet, inaktiveret, eller muteret lacA-gen.
15. Fremgangsmåde ifølge ethvert af de foregående krav, hvor bakterien omfatter en forøget UDP-GIcNAc-produktionskapabilitet.
16. Fremgangsmåde ifølge krav 15, hvor den forøgede UDP-GIcNAc-produktions-kapabilitet omfatter overeksprimering af et nagC-gen, et glmS-gen, et glmY-gen, et glmZ-gen eller en vilkårlig kombination deraf.
17. Fremgangsmåde ifølge krav 15, hvor den forøgede UDP-GIcNAc-produktions-kapabilitet omfatter overeksprimering af E. coli nagC-gen.
18. Fremgangsmåde ifølge krav 15, hvor den forøgede UDP-GIcNAc-produktions-kapabilitet omfatter overeksprimering af nagC og glmS.
19. Fremgangsmåde ifølge krav 15, hvor den forøgede UDP-GIcNAc-produktions-kapabilitet omfatter overeksprimering af nagC og glmY.
20. Fremgangsmåde ifølge krav 15, hvor den forøgede UDP-GIcNAc-produktions-kapabilitet omfatter overeksprimering af nagC og glmZ.
21. Fremgangsmåde ifølge ethvert af de foregående krav, hvor bakterien omfatter E. coli.
22. Fremgangsmåde til fremstilling af et N-acetylglucosamin-holdigt oligosaccharid i en bakterie, omfattende: tilvejebringelse af en bakterie, hvilken bakterie omfatter et exogent UDP-GlcNAc:Gala/3-R β 3-N-acetylglucosaminyltransferasegen og et funktionelt lactose-permeasegen; og dyrkning af bakterien under tilstedeværelse af lactose.
23. Fremgangsmåde ifølge krav 22, hvor bakterien omfatter en forøget UDP-GIcNAc-produktionskapabilitet.
24. Fremgangsmåde ifølge krav 11, hvor den forøgede UDP-GIcNAc-produktions-kapabilitet omfatter overeksprimering af et nagC-gen, et glmS-gen, et glmY-gen, et glmZ-gen eller en vilkårlig kombination deraf.
25. Fremgangsmåde ifølge krav 22, hvor den forøgede UDP-GIcNAc-produktions-kapabilitet omfatter overeksprimering af £. coli nagC-gen.
26. Fremgangsmåde ifølge krav 22, hvor den forøgede UDP-GIcNAc-produktions-kapabilitet omfatter overeksprimering af nagC og glmS.
27. Fremgangsmåde ifølge krav 22, hvor den forøgede UDP-GIcNAc-produktions-kapabilitet omfatter overeksprimering af nagC og glmY.
28. Fremgangsmåde ifølge krav 22, hvor den forøgede UDP-GIcNAc-produktions-kapabilitet omfatter overeksprimering af nagC og glmZ.
29. Fremgangsmåde ifølge ethvert af kravene 22-28, hvor det N-acetylglucosamin-holdige oligosaccharid omfatter en vilkårlig valgt fra Lacto-N-triose 2 (LNT2), Lacto-N-tetraose (LNT), Lacto-N-neotetraose (LNnT), Lacto-N-fucopentaose I (LNF I), Lacto-N-fucopentaose II (LNF II), Lacto-N-fucopentaose III (LNF III), Lacto-N-fucopentaose V (LNF V), Lacto-N-difucohexaose I (LDFH I), Lacto-N-difucohexaose II (LDFH II) og Lacto-N-neodifucohexaose II (LFNnDFH II).
30. Fremgangsmåde ifølge ethvert af kravene 22-29, hvor bakterien er E. coli.
31. Fremgangsmåde til oprensning af sialyleret oligosaccharid fremstillet ved fremgangsmåden ifølge ethvert af kravene 1-21, omfattende binding af det sialylerede oligosaccharid fra et bakteriecellelysat eller bakteriecellekultursupernatant af den nævnte bakterie til en kulstofsøjle og eluering af det sialylerede oligosaccharid fra den nævnte søjle.
32. Fremgangsmåde til oprensning af et N-acetylglucosaminholdigt oligosaccharid fremstillet ved fremgangsmåden ifølge ethvert af kravene 22-30, omfattende binding af det sialylerede oligosaccharid fra et bakterielt cellelysat eller en bakteriel cellekultur-supernatant af den nævnte bakterie til en kulstofsøjle, og eluering af det sialylerede oligosaccharid fra den nævnte søjle.
33. En isoleret E. coli bakterie omfattende et fjernet eller inaktiveret endogent β-galactosidasegen, et exogent sialyltransferasegen, en deficient sialinsyre katabolisk proces, en sialinsyre syntetisk kapabilitet, og et funktionelt lactosepermeasegen.
34. Isoleret bakterie ifølge krav 33, hvor bakterien yderligere omfatter et rekombinant β-galactosidasegen, som tilvejebringer et lavt men detekterbart niveau for β-galactosidaseaktivitet.
35. En isoleret E. coli bakterie omfattende et exogent UDP-GlcNAc:Gala^-R β 3-N-acetylglucosaminyltransferasegen og et funktionelt lactosepermeasegen.
36. Isoleret E. coli bakterie ifølge ethvert af kravene 33-35, hvor bakterien yderligere omfatter en forøget UDP-GIcNAc-produktionskapabilitet.
37. Oprenset sialyleret oligosaccharid fremstillet ved fremgangsmåden ifølge ethvert af kravene 1-21.
38. Oprenset N-acetylglucosaminholdigt oligosaccharid fremstillet ved fremgangsmåden ifølge ethvert af kravene 22-30.
39. Nukleinsyrekonstrukt omfattende et exogent sialyltransferasegen transformeret til en bakteriel værtsstamme omfattende et fjernet eller inaktiveret endogent β-galactosidasegen, en sialinsyresynteseproces, et funktionelt lactosepermeasegen, og et fjernet lactoseacetyltransferasegen.
40. Nukleinsyrekonstrukt ifølge krav 39, hvor det exogene sialyltransferasegen koder a(2,3)-sialyltransferase eller a(2,6)-sialyltransferase.
41. Nukleinsyrekonstrukt omfattende et exogent UDP-GlcNAc:Gala/p-R β 3-N-acetylglucosaminyltransferasegen transformeret til en bakterieværtsstamme omfattende et funktionelt lactosepermeasegen.
42. Fremgangsmåde ifølge ethvert af kravene 1-21, som yderligere omfatter udvinding af det sialylerede oligosaccharid fra bakterien eller fra en kultursupernatant af bakterien.
43. Fremgangsmåde ifølge ethvert af kravene 22-29, som yderligere omfatter udvinding af det N-acetylglucosaminholdige oligosaccharid fra bakterien eller fra en kultursupernatant af bakterien.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361782999P | 2013-03-14 | 2013-03-14 | |
| PCT/US2014/029804 WO2014153253A1 (en) | 2013-03-14 | 2014-03-14 | Microorganisms and methods for producing sialylated and n-acetylglucosamine-containing oligosaccharides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK2970872T1 true DK2970872T1 (da) | 2016-05-09 |
| DK2970872T3 DK2970872T3 (da) | 2019-01-02 |
Family
ID=51581464
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK14769797.3T DK2970872T3 (da) | 2013-03-14 | 2014-03-14 | Mikroorganismer og fremgangsmåder til fremstilling af sialylerede og N-acetylglucosamin-holdige oligosaccharider |
| DK18192520.7T DK3467100T3 (da) | 2013-03-14 | 2014-03-14 | Mikroorganismer og fremgangsmåder til fremstilling af sialylerede og n-acetylglucosamin-holdige oligosaccharider |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK18192520.7T DK3467100T3 (da) | 2013-03-14 | 2014-03-14 | Mikroorganismer og fremgangsmåder til fremstilling af sialylerede og n-acetylglucosamin-holdige oligosaccharider |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US9758803B2 (da) |
| EP (3) | EP2970872B1 (da) |
| CA (1) | CA2904091A1 (da) |
| DE (1) | DE14769797T1 (da) |
| DK (2) | DK2970872T3 (da) |
| ES (2) | ES2930286T3 (da) |
| HU (1) | HUE060672T2 (da) |
| WO (1) | WO2014153253A1 (da) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9567361B2 (en) | 2011-05-13 | 2017-02-14 | Glycosyn LLC | Use of purified 2′-fucosyllactose, 3-fucosyllactose and lactodifucotetraose as prebiotics |
| US10281064B2 (en) * | 2012-11-16 | 2019-05-07 | Kongsberg Actuation Systems Ii, Inc. | Method of forming a hose assembly |
| ES2930286T3 (es) | 2013-03-14 | 2022-12-09 | Glycosyn LLC | Microorganismos y métodos para producir oligosacáridos sialilados y que contienen N-acetilglucosamina |
| US9688970B2 (en) * | 2013-10-01 | 2017-06-27 | Kentucky Bioprocessing, Inc. | Plant-based recombinant butyrylcholinesterase production methods |
| CN106460024B (zh) | 2014-06-27 | 2021-10-01 | 格礼卡姆股份公司 | 寡糖的制备 |
| US11926858B2 (en) | 2014-06-27 | 2024-03-12 | Glycom A/S | Oligosaccharide production |
| SG11201700296YA (en) * | 2014-07-14 | 2017-02-27 | Basf Se | Biotechnological production of lnt, lnnt and the fucosylated derivatives thereof |
| EP3229595B1 (en) | 2014-12-12 | 2021-02-03 | The Regents of the University of California | Reduction of milk glycans and their degradation products in the neonate gut |
| DE202017007249U1 (de) | 2016-03-07 | 2020-04-23 | Glycom A/S | Abtrennung von Oligosacchariden aus der Fermentationsbrühe |
| WO2017174039A1 (zh) * | 2016-04-05 | 2017-10-12 | 孙镧 | 微生物发酵生产n-乙酰-d-氨基葡萄糖和/或d-氨基葡萄糖盐的方法 |
| CN107267576B (zh) * | 2016-04-05 | 2020-08-21 | 孙镧 | 微生物发酵生产n-乙酰-d-氨基葡萄糖和/或d-氨基葡萄糖盐的方法 |
| WO2017174037A1 (zh) * | 2016-04-05 | 2017-10-12 | 孙镧 | 微生物发酵生产n-乙酰-d-氨基葡萄糖和/或d-氨基葡萄糖盐的方法 |
| EP4674526A3 (en) | 2016-04-19 | 2026-04-01 | Glycom A/S | Separation of oligosaccharides from fermentation broth |
| WO2017221208A1 (en) | 2016-06-24 | 2017-12-28 | Glycom A/S | Compositions comprising hmos, their production and use for the prevention and/or treatment of viral and/or bacterial infections |
| US10407516B2 (en) | 2016-10-31 | 2019-09-10 | Glycom A/S | Crystalline HMO |
| US10633682B2 (en) | 2017-03-07 | 2020-04-28 | DePuy Synthes Products, Inc. | Bioresorbable exopolysaccharides |
| WO2018165077A1 (en) | 2017-03-07 | 2018-09-13 | DePuy Synthes Products, Inc. | Bioresorbable exopolysaccharides |
| EP3645545A4 (en) | 2017-06-30 | 2021-05-05 | Glycom A/S | PURIFICATION OF OLIGOSACCHARIDES |
| EP3652189A4 (en) | 2017-07-12 | 2021-04-21 | Glycom A/S | AMORPHIC MIXTURE CONSISTING OF A NEUTRAL MONO- OR OLIGOSACCHARIDE AND A NON-GLUCIDIC ACID COMPONENT |
| KR102897437B1 (ko) * | 2017-07-26 | 2025-12-08 | 크리스찬 한센 에이치엠오 게엠베하 | 시알릴트랜스퍼라제 및 시알릴화 올리고당류 생산에서의 그의 용도 |
| CN107312738B (zh) * | 2017-07-26 | 2020-03-06 | 江南大学 | 一种高效生产果糖软骨素的重组大肠杆菌及其构建方法 |
| EP3688005A1 (en) | 2017-09-29 | 2020-08-05 | FrieslandCampina Nederland B.V. | Process for the purification of a neutral human milk oligosaccharide (hmo) from microbial fermentation |
| EP3473644A1 (en) * | 2017-10-17 | 2019-04-24 | Jennewein Biotechnologie GmbH | Fermentative production of n-acetylneuraminic acid |
| CN107739728A (zh) * | 2017-10-19 | 2018-02-27 | 江南大学 | 一种高效生产氨基葡萄糖的重组大肠杆菌及其应用 |
| EP3486326A1 (en) * | 2017-11-21 | 2019-05-22 | Jennewein Biotechnologie GmbH | Method for the purification of n-acetylneuraminic acid from a fermentation broth |
| JP2021506337A (ja) * | 2017-12-15 | 2021-02-22 | グリコシン リミテッド ライアビリティー カンパニー | シアリルトランスフェラーゼおよびその使用 |
| ES2933995T3 (es) * | 2018-05-28 | 2023-02-15 | Chr Hansen Hmo Gmbh | Producción fermentativa de sacáridos sialilados |
| CN109735480B (zh) * | 2019-02-27 | 2021-11-12 | 光明乳业股份有限公司 | 一种合成乳酰-n-新四糖的重组枯草芽孢杆菌及其构建方法与应用 |
| CN109825465B (zh) * | 2019-02-27 | 2021-11-12 | 光明乳业股份有限公司 | 基于平衡udp-糖供给合成乳酰-n-新四糖的重组枯草芽孢杆菌及其构建方法与应用 |
| CN110066801B (zh) * | 2019-04-30 | 2021-01-29 | 江南大学 | 一种枯草芽孢杆菌中唾液酸诱导表达元件及构建方法 |
| EP3772539A1 (en) * | 2019-08-08 | 2021-02-10 | Jennewein Biotechnologie GmbH | Sialyltransferases for the production of 6'-sialyllactose |
| EP3789495A1 (en) * | 2019-09-03 | 2021-03-10 | Jennewein Biotechnologie GmbH | Production of sialylated oligosaccharides in bacillus cells |
| WO2021019104A2 (en) | 2019-09-18 | 2021-02-04 | Basf Se | A production host for producing human milk oligosaccharides |
| CA3171158A1 (en) | 2020-02-14 | 2021-08-19 | Inbiose N.V. | Kdo-free production hosts for oligosaccharide synthesis |
| EP3954778B1 (en) | 2020-08-10 | 2023-10-04 | Inbiose N.V. | Production of a mixture of neutral non-fucosylated oligosaccharides by a cell |
| AU2021273198A1 (en) | 2020-05-13 | 2023-02-02 | Glycosyn LLC | Fucosylated oligosaccharides for prevention of coronavirus infection |
| WO2021231750A1 (en) | 2020-05-13 | 2021-11-18 | Glycosyn LLC | 2'-fucosyllactose for the prevention and treatment of coronavirus-induced inflammation |
| CN116323930A (zh) * | 2020-08-10 | 2023-06-23 | 因比奥斯公司 | 唾液酸化双糖及/或寡糖的细胞生产 |
| EP4192969A1 (en) * | 2020-08-10 | 2023-06-14 | Inbiose N.V. | Production of an oligosaccharide mixture by a cell |
| US20240368651A1 (en) * | 2020-08-10 | 2024-11-07 | Inbiose N.V. | Cellular production of di- and/or oligosaccharides |
| CN116261398A (zh) | 2020-10-16 | 2023-06-13 | 雀巢产品有限公司 | 包含人乳低聚糖的营养组合物 |
| JP2023547175A (ja) | 2020-11-10 | 2023-11-09 | ソシエテ・デ・プロデュイ・ネスレ・エス・アー | 栄養組成物 |
| KR20230124995A (ko) * | 2020-12-22 | 2023-08-28 | 크리스찬 한센 에이치엠오 게엠베하 | 6'-시알릴락토스의 생산을 위한 시알릴트랜스퍼라제 |
| EP4396209A4 (en) * | 2021-09-02 | 2025-12-17 | Amyris Inc | METHOD FOR THE PRODUCTION OF HUMAN LACTOLOGICAL ACCHARIDS AND COMPOSITIONS THEREOF |
| CN114350584B (zh) * | 2021-12-17 | 2024-03-01 | 嘉必优生物技术（武汉）股份有限公司 | 高产唾液酸乳糖的工程菌及其构建方法与应用 |
| AU2023246643A1 (en) | 2022-04-01 | 2024-10-10 | Inbiose N.V. | Sialyltransferases for the production of sialylated oligosaccharides |
| DK182291B1 (en) | 2022-12-09 | 2026-02-20 | Dsm Ip Assets Bv | Genetically modified udp-n- acetylglucosamine producing cells and methods using the same |
| KR20250144450A (ko) * | 2023-02-07 | 2025-10-10 | 인바이오스 엔.브이. | UDP-GlcNAc 의 합성이 감소된 세포에 의한 이당류 및/또는 젖 올리고당류의 생산 |
| CN116478894B (zh) * | 2023-03-21 | 2025-06-24 | 江南大学 | 一种提高唾液酸乳糖产量的基因工程菌及其生产方法 |
| DK181822B1 (en) * | 2023-06-07 | 2025-01-30 | Dsm Ip Assets Bv | Genetically engineered strains with reduced byproduct formation and methods and uses of same |
| AU2024288910A1 (en) | 2023-07-06 | 2026-01-08 | Societe Des Produits Nestle S.A. | Combination for dietary management of gut health |
| WO2025045721A1 (en) * | 2023-08-25 | 2025-03-06 | Chr. Hansen A/S | N-acetylglucosaminyltransferase enzymes with altered substrate specificity and their use in fermentative oligosaccharide production |
| WO2025224348A1 (en) | 2024-04-26 | 2025-10-30 | Inbiose N.V. | Production of a milk oligosaccharide mixture |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2796082B1 (fr) | 1999-07-07 | 2003-06-27 | Centre Nat Rech Scient | Procede de production d'oligosaccharides |
| EP1789570A2 (en) | 2004-09-17 | 2007-05-30 | Neose Technologies, Inc. | Production of oligosaccharides by microorganisms |
| DK1991690T3 (da) * | 2006-03-09 | 2014-04-14 | Centre Nat Rech Scient | Fremgangsmåde til fremstilling af sialylerede oligosaccharider |
| WO2008097366A2 (en) | 2006-09-26 | 2008-08-14 | Syracuse University | Metabolically engineered escherichia coli for enchanced production of sialic acid |
| US20110165626A1 (en) | 2006-10-03 | 2011-07-07 | Centre National De La Recherche Scientifique (Cnrs | High yield production of sialic acid (neu5ac) by fermentation |
| CA2682735C (en) * | 2007-04-16 | 2015-06-23 | Momenta Pharmaceuticals, Inc. | Multi-dimensional chromatographic methods for separating n-glycans |
| DE12746649T1 (de) | 2011-02-16 | 2016-09-29 | Glycosyn LLC | Biosynthese menschlicher milcholigosaccaride in manipulierten Bakterien |
| US9567361B2 (en) | 2011-05-13 | 2017-02-14 | Glycosyn LLC | Use of purified 2′-fucosyllactose, 3-fucosyllactose and lactodifucotetraose as prebiotics |
| US9029136B2 (en) | 2012-07-25 | 2015-05-12 | Glycosyn LLC | Alpha (1,2) fucosyltransferases suitable for use in the production of fucosylated oligosaccharides |
| ES2930286T3 (es) | 2013-03-14 | 2022-12-09 | Glycosyn LLC | Microorganismos y métodos para producir oligosacáridos sialilados y que contienen N-acetilglucosamina |
| KR20230113650A (ko) | 2014-05-15 | 2023-07-31 | 글리코신 엘엘씨 | 푸코실레이티드 올리고당의 제조에 사용되는 알파(1,2)푸코실트랜스퍼라아제 동질 유전자형 |
-
2014
- 2014-03-14 ES ES18192520T patent/ES2930286T3/es active Active
- 2014-03-14 DK DK14769797.3T patent/DK2970872T3/da active
- 2014-03-14 DE DE14769797.3T patent/DE14769797T1/de active Pending
- 2014-03-14 DK DK18192520.7T patent/DK3467100T3/da active
- 2014-03-14 EP EP14769797.3A patent/EP2970872B1/en active Active
- 2014-03-14 EP EP18192520.7A patent/EP3467100B1/en not_active Revoked
- 2014-03-14 ES ES14769797T patent/ES2700274T3/es active Active
- 2014-03-14 WO PCT/US2014/029804 patent/WO2014153253A1/en not_active Ceased
- 2014-03-14 HU HUE18192520A patent/HUE060672T2/hu unknown
- 2014-03-14 CA CA2904091A patent/CA2904091A1/en active Pending
- 2014-03-14 US US14/776,216 patent/US9758803B2/en not_active Expired - Fee Related
- 2014-03-14 EP EP22196607.0A patent/EP4166650A1/en not_active Withdrawn
-
2017
- 2017-09-11 US US15/700,978 patent/US10415069B2/en active Active
-
2019
- 2019-08-28 US US16/554,460 patent/US11618912B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2970872A1 (en) | 2016-01-20 |
| EP4166650A1 (en) | 2023-04-19 |
| US11618912B2 (en) | 2023-04-04 |
| DE14769797T1 (de) | 2016-06-23 |
| US9758803B2 (en) | 2017-09-12 |
| US20200190548A1 (en) | 2020-06-18 |
| DK2970872T3 (da) | 2019-01-02 |
| DK3467100T3 (da) | 2022-11-14 |
| EP3467100B1 (en) | 2022-09-21 |
| US20160024543A1 (en) | 2016-01-28 |
| HUE060672T2 (hu) | 2023-04-28 |
| WO2014153253A1 (en) | 2014-09-25 |
| EP3467100A1 (en) | 2019-04-10 |
| CA2904091A1 (en) | 2014-09-25 |
| ES2930286T3 (es) | 2022-12-09 |
| US10415069B2 (en) | 2019-09-17 |
| EP2970872B1 (en) | 2018-09-05 |
| ES2700274T3 (es) | 2019-02-14 |
| US20180057849A1 (en) | 2018-03-01 |
| EP2970872A4 (en) | 2016-11-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK2970872T1 (da) | Mikroorganismer og fremgangsmåder til fremstilling af sialylerede og N-acetylglucosamin-holdige oligosaccharider | |
| US20240318216A1 (en) | Production of Human Milk Oligosaccharides in Microbial Hosts with Engineered Import/Export | |
| JP6889205B2 (ja) | コラン酸、マンノシル化及び／又はフコシル化オリゴ糖を合成するための変異体微生物 | |
| EP3390652B1 (en) | Fermentative production of oligosaccharides | |
| EP3461890B1 (en) | Total fermentation of oligosaccharides | |
| US9701992B2 (en) | Metabolically engineered organisms for the production of added value bio-products | |
| CN116261597A (zh) | α-1,3糖基化形式的Fuc-a1,2-Gal-R的产生 | |
| Xiong et al. | Genomic and phenotypic analyses of exopolysaccharide biosynthesis in Streptococcus thermophilus S-3 | |
| US20230212628A1 (en) | Production of Sialylated Oligosaccharide in Host Cells | |
| DK2675899T1 (da) | Biosyntese af humane mælkeoligosaccharider i manipulerede bakterier | |
| JP2020528280A (ja) | シアリルトランスフェラーゼ及びシアリル化オリゴ糖の生産におけるその使用 | |
| CN116745430A (zh) | 在宿主细胞中产生包含ln3作为核心结构的寡糖 | |
| CN115087740A (zh) | 在宿主细胞中产生糖基化产物 | |
| US20220403431A1 (en) | Glycominimized bacterial host cells | |
| TW202221134A (zh) | 半乳糖化雙醣與寡醣的產生 | |
| CN115135769A (zh) | 用于寡糖合成的不含kdo的生产宿主 | |
| CN114555780A (zh) | 宿主细胞中生物产物的产生 | |
| KR20250142419A (ko) | 락토바이오닉산의 합성이 감소된 세포에 의한 당류의 생산 | |
| KR20250144450A (ko) | UDP-GlcNAc 의 합성이 감소된 세포에 의한 이당류 및/또는 젖 올리고당류의 생산 |