CN104726504A - Method for laccase catalytic synthesis of 5,5'-dehydrodiacetovanillone - Google Patents
Method for laccase catalytic synthesis of 5,5'-dehydrodiacetovanillone Download PDFInfo
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- CN104726504A CN104726504A CN201510142163.8A CN201510142163A CN104726504A CN 104726504 A CN104726504 A CN 104726504A CN 201510142163 A CN201510142163 A CN 201510142163A CN 104726504 A CN104726504 A CN 104726504A
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- acetovanillone
- laccase
- dehydrogenation
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- 108010029541 Laccase Proteins 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title abstract description 12
- 238000007036 catalytic synthesis reaction Methods 0.000 title abstract 2
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000000047 product Substances 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000000243 solution Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002244 precipitate Substances 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract description 5
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 17
- 238000010189 synthetic method Methods 0.000 claims description 8
- 238000013016 damping Methods 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- XPFJYKARVSSRHE-UHFFFAOYSA-K trisodium;2-hydroxypropane-1,2,3-tricarboxylate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound [Na+].[Na+].[Na+].OC(=O)CC(O)(C(O)=O)CC(O)=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O XPFJYKARVSSRHE-UHFFFAOYSA-K 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- IEHIPPDDMCEYPI-UHFFFAOYSA-L disodium propanedioate propanedioic acid Chemical compound [Na+].[Na+].OC(=O)CC(O)=O.[O-]C(=O)CC([O-])=O IEHIPPDDMCEYPI-UHFFFAOYSA-L 0.000 claims description 2
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 claims description 2
- 229940074404 sodium succinate Drugs 0.000 claims description 2
- ZEFCBWQRHWLUTC-UHFFFAOYSA-M sodium;2,3-dihydroxybutanedioic acid;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [Na+].OC(=O)C(O)C(O)C(O)=O.OC(=O)C(O)C(O)C([O-])=O ZEFCBWQRHWLUTC-UHFFFAOYSA-M 0.000 claims description 2
- LEAHFJQFYSDGGP-UHFFFAOYSA-K trisodium;dihydrogen phosphate;hydrogen phosphate Chemical compound [Na+].[Na+].[Na+].OP(O)([O-])=O.OP([O-])([O-])=O LEAHFJQFYSDGGP-UHFFFAOYSA-K 0.000 claims description 2
- 238000001035 drying Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 239000013043 chemical agent Substances 0.000 abstract description 2
- 229930014626 natural product Natural products 0.000 abstract description 2
- 231100000252 nontoxic Toxicity 0.000 abstract description 2
- 230000003000 nontoxic effect Effects 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 238000001556 precipitation Methods 0.000 abstract description 2
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000007853 buffer solution Substances 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 description 4
- 206010013786 Dry skin Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000004062 sedimentation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HLNDPICGHQGWSU-UHFFFAOYSA-N 1-[3-(5-acetyl-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC(C=2C(=C(OC)C=C(C=2)C(C)=O)O)=C1O HLNDPICGHQGWSU-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 108010031396 Catechol oxidase Proteins 0.000 description 1
- 102000030523 Catechol oxidase Human genes 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000235058 Komagataella pastoris Species 0.000 description 1
- 102000004722 NADPH Oxidases Human genes 0.000 description 1
- 108010002998 NADPH Oxidases Proteins 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- -1 aromatic amine compound Chemical class 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 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 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003259 recombinant expression Methods 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention discloses a method for laccase catalytic synthesis of 5,5'-dehydrodiacetovanillone. The method comprises the following steps: dissolving acetovanillone into water or a buffer solution with the pH value of 3.5-6.0 to prepare a solution, controlling the temperature to be 20-60 DEG C, adding recombinant laccase, and reacting in a swing bed; standing for precipitation after the reaction, washing a precipitate, and drying at a temperature of not more than 50 DEG C to obtain a product namely 5,5'-dehydrodiacetovanillone. The reaction raw materials and the recombinant laccase are intrinsically natural products and are nontoxic, oxygen in the air is used during reaction, and other oxidants are not needed to be added; and the method disclosed by the invention is mild in reaction condition and can be implemented at room temperature, the product is single and easy to purify, chemical agents including acids, bases and the like are not involved in a purification step, and the product is high in purity.
Description
Technical field
The present invention relates to biocatalysis and field of bioconversion, be specifically related to a kind of 5, the Laccase Catalyzed synthetic method of 5 '-dehydrogenation two Acetovanillone.
Background technology
Acetovanillone is a kind of active substance separated in plant materials, nadph oxidase can be suppressed specifically active, have anti-oxidant and anti-inflammatory activity, and is used to treat parkinsonism.At nature, 5,5 '-dehydrogenation two Acetovanillone (
dehydrodiacetovanillone,cAS:29799-22-2) be the meta-bolites of Acetovanillone, be the trapping agent of superoxide anion, be considered to, than Acetovanillone, there is higher activity, but this product in vivo only trace exist.
Current is Material synthesis 5 with Acetovanillone, and the method for 5 '-dehydrogenation two Acetovanillone mainly contains two kinds.One is chemical method, and employing persulphate is oxygenant, take ferrous sulfate as initiator, reacts 5min when 100 ° of C.At the end of reaction, product precipitates because of water insoluble, but some molysite, persulphate and vitriol also can get off by coprecipitation simultaneously.Follow-up needs uses NH
4throw out dissolves by OH or NaOH solution again, then carries out redeposition with HCl solution, and to remove impurity, finally with boiling water repeatedly washing precipitation, efficiency of pcr product is about 60%.In this technique, because persulfate oxidation is comparatively strong, side chain often can be caused to rupture, thus form low molecular weight substance; Tripolymer may be had generate simultaneously.Visible, although the chemical synthesis reaction times is short, subsequent purification is comparatively complicated, needs to consume the pharmaceutical chemicalss such as more soda acid, simultaneously products obtained therefrom purity and yield all lower.Another synthesis a small amount of 5, the method for 5 '-dehydrogenation two Acetovanillone utilizes peroxidase, and most typical is utilize horseradish peroxidase, with H
2o
2for oxygenant, react when pH=4, by filtration washing, obtain product.
Laccase is a kind of polyphenoloxidase of cupric, and redox potential is lower, oxidable single phenol, bis-phenol, amino phenol and aromatic amine compound, can directly with O
2for electron transit mediator realizes redoxomorphism, after reaction, unique by product is exactly water.Restructuring laccase utilizes molecular biotechnology, the product prepared by DNA recombinant expression, has high, active high, the redox potential advantages of higher of purity.
Summary of the invention
The invention provides a kind of eco-friendly, that technique is simple, efficiency is high, production cost is low Laccase Catalyzed and prepare 5, the method for 5 '-dehydrogenation two Acetovanillone, for it, further production and application lay the foundation.
A kind of 5, the Laccase Catalyzed synthetic method of 5 '-dehydrogenation two Acetovanillone, comprises the steps:
(1) Acetovanillone is dissolved in water or pH is in the buffered soln of 3.5 ~ 6.0, be mixed with solution, control temperature, at 20 ~ 60 ° of C, adds restructuring laccase, reacts in shaking table;
(2) reaction staticly settles after terminating, washing precipitate, dry at not higher than 50 DEG C, obtains product 5,5 '-dehydrogenation two Acetovanillone.
In step (1), the volumetric molar concentration of described Acetovanillone solution is 33 mmol/L; Shaking speed is 120 ~ 150 rpm, and the reaction times is greater than 4 h; Described restructuring laccase consumption is 3.0 ~ 6.0 U/mol Acetovanillones.
In step (1), described damping fluid is selected from the one in Acetic acid-sodium acetate, phosphoric acid-sodium phosphate, citric acid-sodium citrate, tartrate-sodium tartrate, succsinic acid-sodium succinate, propanedioic acid-sodium malonate aqueous solution.
Compared with prior art, advantage of the present invention is:
1. reaction raw materials and restructuring laccase itself are natural product, nontoxic, utilize the oxygen in air, do not need to add other oxygenants in reaction process;
2. reaction conditions is gentle, can carry out under room temperature;
3. product is single, is easy to purifying, does not relate to the chemical agents such as soda acid in purification step, and product purity is high.
Accompanying drawing explanation
Fig. 1 is raw material Acetovanillone (a) and embodiment 1(b), embodiment 2(c) the HPLC figure of product.
Embodiment
(3) reference (Xie pressed by restructuring laccase of the present invention, H. F., Li, Q., Wang, M. M., and Zhao, L. G. (2013) Production of a Recombinant Laccase from Pichia pastoris and Biodegradation of Chlorpyrifos in a Laccase/Vanillin System
j Microbiol Biotechn23, 864-871.) and middle method preparation also purifying.
The measuring method of laccase activity of the present invention is: adopt 1cm light path cuvette, utilize ultraviolet spectrophotometer to measure, determined wavelength is 465nm.Damping fluid is the citric acid-sodium citrate damping fluid of the pH 5.0 of 50mM, and containing 1.8 mL damping fluids in 2mL reaction system, 0.9 mL 2.5 mM methyl catechol solution and 0.1 mL are through certain laccase diluted.Be determined at 30 ° of C to carry out, record the change of 3 min absorbance A, calculate the changing value A of average minute clock absorbancy, be calculated as follows laccase activity, wherein specific absorbance is 1.2 ' 10
4m
-1× cm
-1:
embodiment 1
6.6 mmol Acetovanillones are dissolved in 200mL water, restructuring laccase is added by the consumption of 6.0 U/mol Acetovanillones, 4 h are reacted in 30 ° of C 150rpm shaking tables, after reaction terminates, by sedimentation and filtration, and precipitate 3 times with 100 ° of C hot washes, in 50 ° of C dryings, obtain white powder dehydrogenation two Acetovanillone product, purity is 96.9%, and yield is 94%.
embodiment 2
6.6 mmol Acetovanillones being dissolved in 200mL concentration is in pH 5.0 citric acid-sodium citrate buffer of 50 mM, restructuring laccase is added by the consumption of 3.0 U/mol Acetovanillones, 24 h are reacted in 30 ° of C 150rpm shaking tables, after reaction terminates, by sedimentation and filtration, and precipitate 3 times with 100 ° of C hot washes, in 50 ° of C dryings, obtain pale yellow powder shape dehydrogenation two Acetovanillone product, purity is 97.0%, and yield is 88%.
embodiment 3
6.6 mmol Acetovanillones are dissolved in 200mL water, Corilus versicolor Quel. source laccase is added by the consumption of 6.0 U/mol Acetovanillones, 4 h are reacted in 30 ° of C 150rpm shaking tables, after reaction terminates, by sedimentation and filtration, and precipitate 3 times with 100 ° of C hot washes, in 50 ° of C dryings, obtain pale yellow powder shape product, purity is 83.3%, and yield is 81%.
Fig. 1 is the HPLC spectrogram of embodiment 1 and embodiment 2 Raw and product.Wherein: the retention time of raw material Acetovanillone is 10.7 ~ 10.9min.The retention time of embodiment 1 product, embodiment 2 product is respectively 14.6 and 14.5 min.
Table 1 Acetovanillone and embodiment 1 and embodiment 2 product
1h-NMR modal data
(solvent: DMSO-d
6)
* overlapping with solvent peak.
Data as can be seen from table 1, are polymerized through Laccase Catalyzed the embodiment 1 obtained consistent with document with the hydrogen modal data of embodiment 2 product, meet 5,5 '-dehydrogenation two Acetovanillone chemical structure.
Claims (5)
1. one kind 5, the Laccase Catalyzed synthetic method of 5 '-dehydrogenation two Acetovanillone, is characterized in that, comprise the steps:
(1) Acetovanillone is dissolved in water or pH is in the buffered soln of 3.5 ~ 6.0, be mixed with solution, control temperature, at 20 ~ 60 ° of C, adds restructuring laccase, reacts in shaking table;
(2) reaction staticly settles after terminating, washing precipitate, dry at not higher than 50 DEG C, obtains product 5,5 '-dehydrogenation two Acetovanillone.
2. as claimed in claim 15, the Laccase Catalyzed synthetic method of 5 '-dehydrogenation two Acetovanillone, is characterized in that, the volumetric molar concentration of described Acetovanillone solution is 33 mmol/L.
3. as claimed in claim 15, the Laccase Catalyzed synthetic method of 5 '-dehydrogenation two Acetovanillone, is characterized in that, shaking speed is 120 ~ 150 rpm, and the reaction times is greater than 4 h.
4. as claimed in claim 15, the Laccase Catalyzed synthetic method of 5 '-dehydrogenation two Acetovanillone, is characterized in that, restructuring laccase consumption is 3.0 ~ 6.0 U/mol Acetovanillones.
5. as claimed in claim 15, the Laccase Catalyzed synthetic method of 5 '-dehydrogenation two Acetovanillone, it is characterized in that, damping fluid is selected from the one in Acetic acid-sodium acetate, phosphoric acid-sodium phosphate, citric acid-sodium citrate, tartrate-sodium tartrate, succsinic acid-sodium succinate, propanedioic acid-sodium malonate aqueous solution.
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|---|---|---|---|
| CN201510142163.8A CN104726504B (en) | 2015-03-27 | 2015-03-27 | The Laccase Catalyzed synthetic method of 5,5 '-dehydrogenation, two Acetovanillone |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115448825A (en) * | 2022-09-30 | 2022-12-09 | 绵阳市斯麦尔顾生物科技有限公司 | Preparation method of bifenaldehyde |
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|---|---|---|---|---|
| CN101967497A (en) * | 2010-07-15 | 2011-02-09 | 池州方达科技有限公司 | Preparation of 2-(6'-methoxy-2'-naphthyl) allyl alcohol by laccase method |
| CN102643886A (en) * | 2012-04-13 | 2012-08-22 | 东华大学 | Method for preparing polymerized rutin by laccase mediator system catalysis |
| CN103088076A (en) * | 2013-01-29 | 2013-05-08 | 南京理工大学 | Method for preparing benzoyl formic acid and R-mandelic acid by coupling reaction of S- mandelic acid dehydrogenase and laccase |
| CN103710363A (en) * | 2013-12-16 | 2014-04-09 | 南京林业大学 | Laccase gene Lac6 and expression protein and application thereof |
| US20140356540A1 (en) * | 2010-12-20 | 2014-12-04 | Cytec Austria Gmbh | Process for curing surface-coating compositions |
-
2015
- 2015-03-27 CN CN201510142163.8A patent/CN104726504B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101967497A (en) * | 2010-07-15 | 2011-02-09 | 池州方达科技有限公司 | Preparation of 2-(6'-methoxy-2'-naphthyl) allyl alcohol by laccase method |
| US20140356540A1 (en) * | 2010-12-20 | 2014-12-04 | Cytec Austria Gmbh | Process for curing surface-coating compositions |
| CN102643886A (en) * | 2012-04-13 | 2012-08-22 | 东华大学 | Method for preparing polymerized rutin by laccase mediator system catalysis |
| CN103088076A (en) * | 2013-01-29 | 2013-05-08 | 南京理工大学 | Method for preparing benzoyl formic acid and R-mandelic acid by coupling reaction of S- mandelic acid dehydrogenase and laccase |
| CN103710363A (en) * | 2013-12-16 | 2014-04-09 | 南京林业大学 | Laccase gene Lac6 and expression protein and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| JULIAN IHSSEN等: "Laccase Catalyzed Synthesis of Iodinated Phenolic Compounds with Antifungal Activity", 《PLOS ONE》 * |
Cited By (1)
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| CN115448825A (en) * | 2022-09-30 | 2022-12-09 | 绵阳市斯麦尔顾生物科技有限公司 | Preparation method of bifenaldehyde |
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