CA2376009A1 - Oxydation biocatalytique a l'aide de peroxydases de soja et d'autres legumineuses - Google Patents
Oxydation biocatalytique a l'aide de peroxydases de soja et d'autres legumineuses Download PDFInfo
- Publication number
- CA2376009A1 CA2376009A1 CA002376009A CA2376009A CA2376009A1 CA 2376009 A1 CA2376009 A1 CA 2376009A1 CA 002376009 A CA002376009 A CA 002376009A CA 2376009 A CA2376009 A CA 2376009A CA 2376009 A1 CA2376009 A1 CA 2376009A1
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- CA
- Canada
- Prior art keywords
- peroxidase
- enzyme
- water
- soybean
- phenol
- 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.)
- Abandoned
Links
- 244000068988 Glycine max Species 0.000 title claims abstract description 51
- 235000010469 Glycine max Nutrition 0.000 title claims abstract description 51
- 102000003992 Peroxidases Human genes 0.000 title claims abstract description 33
- 235000021374 legumes Nutrition 0.000 title abstract description 17
- 230000002210 biocatalytic effect Effects 0.000 title abstract description 15
- 108700020962 Peroxidase Proteins 0.000 title description 19
- 230000003647 oxidation Effects 0.000 title description 14
- 238000007254 oxidation reaction Methods 0.000 title description 14
- 108040007629 peroxidase activity proteins Proteins 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 70
- 230000008569 process Effects 0.000 claims abstract description 42
- 150000002978 peroxides Chemical class 0.000 claims abstract description 26
- 229920001568 phenolic resin Polymers 0.000 claims abstract description 25
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- 238000000746 purification Methods 0.000 claims abstract description 6
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 58
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- 102000004169 proteins and genes Human genes 0.000 claims description 20
- 108090000623 proteins and genes Proteins 0.000 claims description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 18
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 17
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- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 6
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- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical group OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims description 6
- 229940033123 tannic acid Drugs 0.000 claims description 6
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 claims description 4
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 claims description 4
- 239000002609 medium Substances 0.000 claims description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- 239000013638 trimer Substances 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
- 235000011152 sodium sulphate Nutrition 0.000 claims description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 2
- PSAGPCOTGOTBQB-UHFFFAOYSA-N 4-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(O)C2=C1 PSAGPCOTGOTBQB-UHFFFAOYSA-N 0.000 claims description 2
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 claims description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 2
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 claims description 2
- 229960004909 aminosalicylic acid Drugs 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 229930003836 cresol Natural products 0.000 claims description 2
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 claims description 2
- 229940005667 ethyl salicylate Drugs 0.000 claims description 2
- 229960001047 methyl salicylate Drugs 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- XSPLAZUGLAABRK-UHFFFAOYSA-N 4-octylphenol;4-phenylphenol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1.CCCCCCCCC1=CC=C(O)C=C1 XSPLAZUGLAABRK-UHFFFAOYSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 abstract description 11
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- 238000005691 oxidative coupling reaction Methods 0.000 abstract description 3
- 102000013415 peroxidase activity proteins Human genes 0.000 description 81
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 38
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- 150000002989 phenols Chemical class 0.000 description 24
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- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- OABYVIYXWMZFFJ-ZUHYDKSRSA-M sodium glycocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 OABYVIYXWMZFFJ-ZUHYDKSRSA-M 0.000 description 1
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- 150000008163 sugars Chemical class 0.000 description 1
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- 239000001648 tannin Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/599,584 US5147793A (en) | 1990-10-18 | 1990-10-18 | Biocatalytic oxidation using soybean peroxidases |
| US599,584 | 1990-10-18 | ||
| CA002053547A CA2053547C (fr) | 1990-10-18 | 1991-10-16 | Oxydation biocatalytique a l'aide de peroxydases de soja et d'autres legumineuses |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002053547A Division CA2053547C (fr) | 1990-10-18 | 1991-10-16 | Oxydation biocatalytique a l'aide de peroxydases de soja et d'autres legumineuses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2376009A1 true CA2376009A1 (fr) | 1992-04-19 |
Family
ID=25674820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002376009A Abandoned CA2376009A1 (fr) | 1990-10-18 | 1991-10-16 | Oxydation biocatalytique a l'aide de peroxydases de soja et d'autres legumineuses |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2376009A1 (fr) |
-
1991
- 1991-10-16 CA CA002376009A patent/CA2376009A1/fr not_active Abandoned
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