DE2149653A1 - Synthese-Verfahren fuer die Herstellung von Ascorbinsaeureglukoside - Google Patents
Synthese-Verfahren fuer die Herstellung von AscorbinsaeureglukosideInfo
- Publication number
- DE2149653A1 DE2149653A1 DE19712149653 DE2149653A DE2149653A1 DE 2149653 A1 DE2149653 A1 DE 2149653A1 DE 19712149653 DE19712149653 DE 19712149653 DE 2149653 A DE2149653 A DE 2149653A DE 2149653 A1 DE2149653 A1 DE 2149653A1
- Authority
- DE
- Germany
- Prior art keywords
- ascorbic acid
- aspergillus
- iam
- glucoside
- enzyme
- 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
Links
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 title claims description 81
- 239000011668 ascorbic acid Substances 0.000 title claims description 54
- 229960005070 ascorbic acid Drugs 0.000 title claims description 51
- 235000010323 ascorbic acid Nutrition 0.000 title claims description 50
- 229930182478 glucoside Natural products 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 23
- -1 ascorbic acid glucosides Chemical class 0.000 title claims description 21
- 230000008569 process Effects 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 230000015572 biosynthetic process Effects 0.000 title description 9
- 238000003786 synthesis reaction Methods 0.000 title description 3
- 108090000790 Enzymes Proteins 0.000 claims description 35
- 102000004190 Enzymes Human genes 0.000 claims description 35
- 150000001720 carbohydrates Chemical class 0.000 claims description 16
- 241000228212 Aspergillus Species 0.000 claims description 15
- 241000228143 Penicillium Species 0.000 claims description 12
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 10
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products 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-PICCSMPSSA-N 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 9
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
- 229920001542 oligosaccharide Polymers 0.000 claims description 7
- 241000122821 Aspergillus kawachii Species 0.000 claims description 5
- 241000228251 Aspergillus phoenicis Species 0.000 claims description 5
- 241001112078 Aspergillus usamii Species 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 230000002255 enzymatic effect Effects 0.000 claims description 5
- 241001513093 Aspergillus awamori Species 0.000 claims description 4
- 241001540751 Talaromyces ruber Species 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 3
- 241000228150 Penicillium chrysogenum Species 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000004362 fungal culture Methods 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 235000015047 pilsener Nutrition 0.000 claims 1
- 230000035943 smell Effects 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 description 44
- 229940088598 enzyme Drugs 0.000 description 32
- 239000000047 product Substances 0.000 description 29
- 239000000203 mixture Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 150000008131 glucosides Chemical class 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229960002160 maltose Drugs 0.000 description 9
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 8
- 239000008351 acetate buffer Substances 0.000 description 7
- 239000007853 buffer solution Substances 0.000 description 7
- 238000004816 paper chromatography Methods 0.000 description 7
- 240000007124 Brassica oleracea Species 0.000 description 6
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- 239000002151 riboflavin Substances 0.000 description 6
- 229960002477 riboflavin Drugs 0.000 description 6
- 235000019192 riboflavin Nutrition 0.000 description 6
- 241000228245 Aspergillus niger Species 0.000 description 5
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 5
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 5
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 5
- 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 5
- 238000009835 boiling Methods 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 150000002482 oligosaccharides Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- 229940046892 lead acetate Drugs 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 235000015099 wheat brans Nutrition 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 150000000996 L-ascorbic acids Chemical class 0.000 description 3
- 241000235395 Mucor Species 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 229940072107 ascorbate Drugs 0.000 description 3
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 3
- 150000001719 carbohydrate derivatives Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- NZZFEUNDIKEEJZ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[2-(3,4,5-trihydroxy-6-methoxyoxan-2-yl)ethyl]oxane-3,4,5-triol Chemical compound OC1C(O)C(O)C(OC)OC1CCC1C(O)C(O)C(O)C(CO)O1 NZZFEUNDIKEEJZ-UHFFFAOYSA-N 0.000 description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 108010015776 Glucose oxidase Proteins 0.000 description 2
- 239000004366 Glucose oxidase Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229910001431 copper ion Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000174 gluconic acid Substances 0.000 description 2
- 235000012208 gluconic acid Nutrition 0.000 description 2
- 229940116332 glucose oxidase Drugs 0.000 description 2
- 235000019420 glucose oxidase Nutrition 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- HBDJFVFTHLOSDW-DNDLZOGFSA-N (2r,3r,4r,5r)-2,3,5,6-tetrahydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal;hydrate Chemical compound O.O=C[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HBDJFVFTHLOSDW-DNDLZOGFSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002245 Dextrose equivalent Polymers 0.000 description 1
- 241000192132 Leuconostoc Species 0.000 description 1
- 241000192130 Leuconostoc mesenteroides Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 244000182022 Salvia sclarea Species 0.000 description 1
- 235000002911 Salvia sclarea Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910000004 White lead Inorganic materials 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000003851 biochemical process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 239000006787 czapek-dox agar Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical compound CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PIJPYDMVFNTHIP-UHFFFAOYSA-L lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- 229960003017 maltose monohydrate Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 235000019187 sodium-L-ascorbate Nutrition 0.000 description 1
- 239000011755 sodium-L-ascorbate Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- 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
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
- Y10S435/913—Aspergillus
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
- Y10S435/913—Aspergillus
- Y10S435/914—Aspergillus awamori
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
- Y10S435/933—Penicillium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
- Y10S435/933—Penicillium
- Y10S435/935—Penicillium chrysogenum
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45087419A JPS4838158B1 (enExample) | 1970-10-05 | 1970-10-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2149653A1 true DE2149653A1 (de) | 1972-04-13 |
Family
ID=13914342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712149653 Pending DE2149653A1 (de) | 1970-10-05 | 1971-10-05 | Synthese-Verfahren fuer die Herstellung von Ascorbinsaeureglukoside |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3763009A (enExample) |
| JP (1) | JPS4838158B1 (enExample) |
| DE (1) | DE2149653A1 (enExample) |
| GB (1) | GB1364279A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0398484A3 (en) * | 1989-05-19 | 1991-02-27 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Alpha-glycosyl-l-ascorbic acid, and its preparation and uses |
| EP0425066A1 (en) * | 1989-10-21 | 1991-05-02 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Crystalline 2-0-alpha-D-glucopyranosyl-L-ascorbic acid, and its preparation and uses |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5154132A (en) * | 1974-11-08 | 1976-05-13 | Nissan Motor | Nainenkikanno nenryoseigyosochi |
| US5215767A (en) * | 1991-03-16 | 1993-06-01 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Additive for aquaculture feed for fish and shellfish and aquaculture feed for fish and shellfish which contains same |
| US5272136A (en) * | 1991-10-12 | 1993-12-21 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | 5-0-α-D-Glucopyranosyl-L-ascorbic acid, and its preparation and uses |
| JP3072535B2 (ja) * | 1991-10-21 | 2000-07-31 | 株式会社林原生物化学研究所 | ５−Ｏ−α−Ｄ−グルコピラノシル−Ｌ−アスコルビン酸とその製造方法並びに用途 |
| JP3134235B2 (ja) * | 1991-10-23 | 2001-02-13 | 株式会社林原生物化学研究所 | ２−Ｏ−α−Ｄ−グルコピラノシル−Ｌ−アスコルビン酸高含有物の製造方法 |
| JP4590041B2 (ja) * | 1998-12-24 | 2010-12-01 | 株式会社林原生物化学研究所 | 臓器保存剤 |
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-
1970
- 1970-10-05 JP JP45087419A patent/JPS4838158B1/ja active Pending
-
1971
- 1971-10-04 US US00186387A patent/US3763009A/en not_active Expired - Lifetime
- 1971-10-04 GB GB4609371A patent/GB1364279A/en not_active Expired
- 1971-10-05 DE DE19712149653 patent/DE2149653A1/de active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0398484A3 (en) * | 1989-05-19 | 1991-02-27 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Alpha-glycosyl-l-ascorbic acid, and its preparation and uses |
| EP0425066A1 (en) * | 1989-10-21 | 1991-05-02 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Crystalline 2-0-alpha-D-glucopyranosyl-L-ascorbic acid, and its preparation and uses |
| EP0627441A1 (en) * | 1989-10-21 | 1994-12-07 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Crystalline 2-0-alpha-D-glucopyranosyl-L-ascorbic acid, and its preparation and uses |
| US5407812A (en) * | 1989-10-21 | 1995-04-18 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Crystalline 2-O-α-D-glucopyranosyl-L-ascorbic acid, and its preparation and uses |
| US5432161A (en) * | 1989-10-21 | 1995-07-11 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Crystalline 2-O-α-d-glucopyranosyl-L-ascorbic acid, and its preparation and uses |
| US5843907A (en) * | 1989-10-21 | 1998-12-01 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Pharmaceutical composition containing 2-O-α-d-glucopyranosyl-l-ascorbic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1364279A (en) | 1974-08-21 |
| US3763009A (en) | 1973-10-02 |
| JPS4838158B1 (enExample) | 1973-11-15 |
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