DE69328528T2 - D-Ketohexose-3-Epimerase, und seine Herstellung und Verwendung - Google Patents
D-Ketohexose-3-Epimerase, und seine Herstellung und VerwendungInfo
- Publication number
- DE69328528T2 DE69328528T2 DE69328528T DE69328528T DE69328528T2 DE 69328528 T2 DE69328528 T2 DE 69328528T2 DE 69328528 T DE69328528 T DE 69328528T DE 69328528 T DE69328528 T DE 69328528T DE 69328528 T2 DE69328528 T2 DE 69328528T2
- Authority
- DE
- Germany
- Prior art keywords
- ketohexose
- epimerase
- ketose
- enzyme
- ketopentose
- 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.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title description 7
- 208000007976 Ketosis Diseases 0.000 claims description 26
- 150000002584 ketoses Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 15
- 235000003599 food sweetener Nutrition 0.000 claims description 11
- 239000003765 sweetening agent Substances 0.000 claims description 11
- 238000010521 absorption reaction Methods 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 238000000862 absorption spectrum Methods 0.000 claims description 7
- 238000004440 column chromatography Methods 0.000 claims description 6
- 241000589516 Pseudomonas Species 0.000 claims description 4
- 238000006345 epimerization reaction Methods 0.000 claims description 4
- 238000002523 gelfiltration Methods 0.000 claims description 4
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 4
- 238000002264 polyacrylamide gel electrophoresis Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 238000012258 culturing Methods 0.000 claims description 3
- 238000003795 desorption Methods 0.000 claims description 3
- 238000001962 electrophoresis Methods 0.000 claims description 3
- 238000001042 affinity chromatography Methods 0.000 claims description 2
- 230000004140 ketosis Effects 0.000 claims description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 239000003729 cation exchange resin Substances 0.000 claims 2
- 238000011084 recovery Methods 0.000 claims 2
- 241001508466 Pseudomonas cichorii Species 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- -1 alkaline earth metal salt Chemical class 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 235000015097 nutrients Nutrition 0.000 claims 1
- 230000001131 transforming effect Effects 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 description 42
- 108090000790 Enzymes Proteins 0.000 description 42
- 239000000243 solution Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- LKDRXBCSQODPBY-IANNHFEVSA-N D-sorbose Chemical compound OCC1(O)OC[C@@H](O)[C@H](O)[C@H]1O LKDRXBCSQODPBY-IANNHFEVSA-N 0.000 description 14
- LKDRXBCSQODPBY-OEXCPVAWSA-N D-tagatose Chemical compound OCC1(O)OC[C@@H](O)[C@H](O)[C@@H]1O LKDRXBCSQODPBY-OEXCPVAWSA-N 0.000 description 13
- ZAQJHHRNXZUBTE-UCORVYFPSA-N L-ribulose Chemical compound OC[C@H](O)[C@H](O)C(=O)CO ZAQJHHRNXZUBTE-UCORVYFPSA-N 0.000 description 11
- 238000006911 enzymatic reaction Methods 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 10
- ZAQJHHRNXZUBTE-UHFFFAOYSA-N D-threo-2-Pentulose Natural products OCC(O)C(O)C(=O)CO ZAQJHHRNXZUBTE-UHFFFAOYSA-N 0.000 description 10
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- BJHIKXHVCXFQLS-PUFIMZNGSA-N D-psicose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C(=O)CO BJHIKXHVCXFQLS-PUFIMZNGSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000006188 syrup Substances 0.000 description 9
- 235000020357 syrup Nutrition 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 108090001066 Racemases and epimerases Proteins 0.000 description 7
- 102000004879 Racemases and epimerases Human genes 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 150000001720 carbohydrates Chemical class 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 238000000855 fermentation Methods 0.000 description 6
- 230000004151 fermentation Effects 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 5
- ZAQJHHRNXZUBTE-WVZVXSGGSA-N L-xylulose Chemical compound OC[C@H](O)[C@@H](O)C(=O)CO ZAQJHHRNXZUBTE-WVZVXSGGSA-N 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- ZAQJHHRNXZUBTE-WUJLRWPWSA-N D-xylulose Chemical compound OC[C@@H](O)[C@H](O)C(=O)CO ZAQJHHRNXZUBTE-WUJLRWPWSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 150000002574 ketohexoses Chemical class 0.000 description 4
- 150000002581 ketopentoses Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
- 108091022872 aldose 1-epimerase Proteins 0.000 description 3
- 229940098773 bovine serum albumin Drugs 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000009631 Broth culture Methods 0.000 description 2
- 108030002154 Cellobiose epimerases Proteins 0.000 description 2
- 108010038061 Chymotrypsinogen Proteins 0.000 description 2
- 102000018832 Cytochromes Human genes 0.000 description 2
- 108010052832 Cytochromes Proteins 0.000 description 2
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 2
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 108060007030 Ribulose-phosphate 3-epimerase Proteins 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- 102100021436 UDP-glucose 4-epimerase Human genes 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 102000020006 aldose 1-epimerase Human genes 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001952 enzyme assay Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000011565 manganese chloride Substances 0.000 description 2
- 235000002867 manganese chloride Nutrition 0.000 description 2
- 229940099607 manganese chloride Drugs 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229940092253 ovalbumin Drugs 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004688 ribulosephosphate 3-epimerase Human genes 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N 3,4,5,6-tetrahydroxyoxane-2-carboxylic acid Chemical compound OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 description 1
- 244000080767 Areca catechu Species 0.000 description 1
- 235000006226 Areca catechu Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical class O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 150000008164 L-ketoses Chemical class 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 108010075202 UDP-glucose 4-epimerase Proteins 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical group 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 229940111685 dibasic potassium phosphate Drugs 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000001641 gel filtration chromatography Methods 0.000 description 1
- 239000007986 glycine-NaOH buffer Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229940111688 monobasic potassium phosphate Drugs 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 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
- C12P19/24—Preparation of compounds containing saccharide radicals produced by the action of an isomerase, e.g. fructose
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/16—Extraction; Separation; Purification by chromatography
- C07K1/18—Ion-exchange chromatography
-
- 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
- C12N9/90—Isomerases (5.)
-
- 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
- C12P21/00—Preparation of peptides or proteins
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y501/00—Racemaces and epimerases (5.1)
- C12Y501/03—Racemaces and epimerases (5.1) acting on carbohydrates and derivatives (5.1.3)
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Biophysics (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Seasonings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31258092A JP3333969B2 (ja) | 1992-10-08 | 1992-10-08 | Ｄ−ケトヘキソース・３−エピメラーゼとその製造方法並びに用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69328528D1 DE69328528D1 (de) | 2000-06-08 |
| DE69328528T2 true DE69328528T2 (de) | 2000-10-12 |
Family
ID=18030918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69328528T Expired - Fee Related DE69328528T2 (de) | 1992-10-08 | 1993-10-06 | D-Ketohexose-3-Epimerase, und seine Herstellung und Verwendung |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US5411880A (https=) |
| EP (1) | EP0592202B1 (https=) |
| JP (1) | JP3333969B2 (https=) |
| KR (1) | KR100278757B1 (https=) |
| DE (1) | DE69328528T2 (https=) |
| TW (1) | TW232029B (https=) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3333969B2 (ja) * | 1992-10-08 | 2002-10-15 | 株式会社林原生物化学研究所 | Ｄ−ケトヘキソース・３−エピメラーゼとその製造方法並びに用途 |
| JPH08154696A (ja) * | 1994-10-05 | 1996-06-18 | Hayashibara Biochem Lab Inc | Ｌ−ケトヘキソースの製造方法 |
| FI20011889A7 (fi) | 2001-09-26 | 2003-03-27 | Xyrofin Oy | Menetelmä ksylitolin valmistamiseksi |
| EP3115052B1 (en) | 2002-05-22 | 2019-08-21 | Matsutani Chemical Industry Co., Ltd. | D-psicose for use in the treatment of arteriosclerosis |
| JP2005102503A (ja) | 2003-01-10 | 2005-04-21 | Kagawa Univ | 新しい触媒機能を有するｌ−ラムノースイソメラーゼの遺伝子配列およびその用途 |
| JP5240810B2 (ja) * | 2005-07-20 | 2013-07-17 | 帝國製薬株式会社 | Ｄ−プシコースの血中ｄ−フラクトース濃度上昇抑制への使用 |
| JP5030045B2 (ja) * | 2005-09-29 | 2012-09-19 | 国立大学法人 香川大学 | 希少糖を含有する二糖の製造方法 |
| JP4841617B2 (ja) * | 2006-03-03 | 2011-12-21 | 株式会社希少糖生産技術研究所 | 抗線虫用組成物および抗線虫性組成物を用いる線虫制圧法 |
| JP4942001B2 (ja) | 2006-11-10 | 2012-05-30 | 松谷化学工業株式会社 | Ｄ−プシコース含有甘味料およびそれを使用して得られた飲食品など |
| WO2008056453A1 (en) | 2006-11-10 | 2008-05-15 | Matsutani Chemical Industry Co., Ltd. | Noncarious material and anticarious agent containing rare sugar |
| JP5358186B2 (ja) * | 2006-11-20 | 2013-12-04 | 国立大学法人 香川大学 | デオキシケトヘキソース異性化酵素を用いるデオキシヘキソースおよびその誘導体の製造方法 |
| KR20100018568A (ko) * | 2007-05-18 | 2010-02-17 | 마쓰다니가가꾸고오교가부시끼가이샤 | 슈크로오스성 감미질을 가지는 신규 감미료, 그 제조법 및 용도 |
| JP2009254238A (ja) * | 2008-04-11 | 2009-11-05 | Kishoto Seisan Gijutsu Kenkyusho:Kk | ４−ｃ−メチルケトペントース異性化酵素およびそれを用いる４−ｃ−メチルケトペントースの製造方法 |
| US20120040407A1 (en) | 2009-02-05 | 2012-02-16 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Cellobiose 2-epimerase, its preparation and uses |
| JP5876205B2 (ja) * | 2009-02-06 | 2016-03-02 | 松谷化学工業株式会社 | Ｄ−ソルボースからなる甘味料におけるｄ−ソルボースの甘味の不足や、甘味の持続を改良する方法 |
| JP5859191B2 (ja) | 2010-09-29 | 2016-02-10 | 松谷化学工業株式会社 | 高甘味度甘味料に対する呈味改良組成物およびその応用 |
| JP5731784B2 (ja) | 2010-09-29 | 2015-06-10 | 松谷化学工業株式会社 | 食感食味の優れたベーカリー製品及びその製造法 |
| JP6216493B2 (ja) | 2011-06-24 | 2017-10-18 | 国立大学法人 香川大学 | 寿命延長剤 |
| KR101944027B1 (ko) * | 2011-07-06 | 2019-01-30 | 마쓰다니가가꾸고오교가부시끼가이샤 | 아스로박터 글로비포미스가 생산하는 효소 |
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| AU2013250804A1 (en) | 2012-04-17 | 2016-08-11 | Agtive Bio-Sciences Private Limited | Method of production of monosaccharides |
| GB2583417B (en) * | 2012-09-27 | 2021-03-31 | Tate & Lyle Ingredients Americas Llc | A protein |
| US9932617B2 (en) | 2013-01-08 | 2018-04-03 | Matsutani Chemical Industry Co., Ltd. | Ketose 3-epimerase produced by arthrobacter globiformis |
| GB201309076D0 (en) | 2013-03-15 | 2013-07-03 | Tate & Lyle Ingredients | Improved sweetener |
| GB201309079D0 (en) | 2013-03-15 | 2013-07-03 | Tate & Lyle Ingredients | Improved sweetner |
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| KR101868194B1 (ko) * | 2013-11-19 | 2018-06-18 | 씨제이제일제당 (주) | 호열균 유래 당 에피머화효소를 포함하는, 비인산헥소오스의 에피머화용 조성물 |
| WO2018052054A1 (ja) | 2016-09-14 | 2018-03-22 | 松谷化学工業株式会社 | 固定化アルロースエピメラーゼの製造方法 |
| KR102679582B1 (ko) | 2016-10-28 | 2024-06-27 | 테이트 앤드 라일 솔루션스 유에스에이 엘엘씨 | 알룰로오스 결정의 제조방법 |
| US12590116B2 (en) | 2016-10-28 | 2026-03-31 | Tate & Lyle Solutions Usa Llc | Method for producing allulose crystals |
| EP3663397A4 (en) * | 2017-07-31 | 2021-04-28 | CJ Cheiljedang Corporation | NEW PSICOSE-6-PHOSPHATE-PHOSPHATASE, COMPOSITION FOR THE MANUFACTURING OF PSICOSE INCLUDING THIS ENZYME, PROCESS FOR MANUFACTURING PSICOSE USING THIS ENZYME |
| KR102887141B1 (ko) | 2018-11-08 | 2025-11-17 | 고쿠리츠다이가쿠호우징 카가와다이가쿠 | 희소당 함유 조성물의 제조 방법 및 희소당 함유 조성물 |
| EP4000419A1 (de) | 2020-11-23 | 2022-05-25 | Savanna Ingredients GmbH | Trocknung von allulosekristallen |
| EP4338598A4 (en) | 2021-05-07 | 2025-10-08 | Univ Kagawa Nat Univ Corp | METHOD FOR MASS PRODUCTION OF A SWEETENER HAVING A SUGAR-LIKE FLAVOR QUALITY AND POSSESSING D-ALLULOSE FUNCTIONALITY |
| EP4520839A3 (de) | 2023-03-15 | 2025-12-03 | Annikki GmbH | Verfahren zur herstellung einer wässerigen lösung enthaltend d-psicose |
| EP4464786A1 (de) | 2023-05-15 | 2024-11-20 | Annikki GmbH | Verfahren zur herstellung von wässerigen lösungen enthaltend d-psicose oder l-psicose |
| KR20250162615A (ko) | 2023-03-15 | 2025-11-18 | 안니키 게엠베하 | D-프시코스를 함유하는 수용액을 제조하는 방법 |
| EP4431614A1 (de) | 2023-03-15 | 2024-09-18 | Annikki GmbH | Verfahren zur herstellung von wässerigen lösungen enthaltend d-psicose oder l-psicose |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3432570A1 (de) * | 1984-09-05 | 1986-03-13 | Merck Patent Gmbh, 6100 Darmstadt | Verfahren zur mikrobiologischen herstellung von aldose-1-epimerase |
| US4988822A (en) * | 1986-05-29 | 1991-01-29 | Syntex (U.S.A.) Inc. | Intermediates for preparing 5-aroyl-1,2-dihydro-3H-pyrrolo(1,2-A)pyrrole-1,1-dicarboxylates |
| US4981799A (en) * | 1987-08-21 | 1991-01-01 | Takeda Chemical Industries, Ltd. | Acylamino acid racemase, production and use thereof |
| US5085993A (en) * | 1987-12-24 | 1992-02-04 | Hoffmann-La Roche Inc. | Coenzyme-independent l-sorbosone dehydrogenase from pseudomonas putida |
| JP2876417B2 (ja) * | 1990-03-17 | 1999-03-31 | 株式会社林原生物化学研究所 | Ｄ―ソルボースの製造方法 |
| US5168056A (en) * | 1991-02-08 | 1992-12-01 | Purdue Research Foundation | Enhanced production of common aromatic pathway compounds |
| JP3333969B2 (ja) * | 1992-10-08 | 2002-10-15 | 株式会社林原生物化学研究所 | Ｄ−ケトヘキソース・３−エピメラーゼとその製造方法並びに用途 |
-
1992
- 1992-10-08 JP JP31258092A patent/JP3333969B2/ja not_active Expired - Lifetime
-
1993
- 1993-10-06 EP EP93307925A patent/EP0592202B1/en not_active Expired - Lifetime
- 1993-10-06 DE DE69328528T patent/DE69328528T2/de not_active Expired - Fee Related
- 1993-10-07 KR KR1019930020713A patent/KR100278757B1/ko not_active Expired - Fee Related
- 1993-10-07 US US08/132,853 patent/US5411880A/en not_active Expired - Lifetime
- 1993-10-12 TW TW082108435A patent/TW232029B/zh active
-
1995
- 1995-03-30 US US08/413,937 patent/US5679562A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0592202A2 (en) | 1994-04-13 |
| TW232029B (https=) | 1994-10-11 |
| JPH06125776A (ja) | 1994-05-10 |
| EP0592202A3 (en) | 1995-04-05 |
| US5411880A (en) | 1995-05-02 |
| KR940009331A (ko) | 1994-05-20 |
| JP3333969B2 (ja) | 2002-10-15 |
| KR100278757B1 (ko) | 2001-01-15 |
| US5679562A (en) | 1997-10-21 |
| DE69328528D1 (de) | 2000-06-08 |
| EP0592202B1 (en) | 2000-05-03 |
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