EP0677102A1 - Amelioration de reactions enzymatiques - Google Patents

Amelioration de reactions enzymatiques

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Publication number
EP0677102A1
EP0677102A1 EP94900786A EP94900786A EP0677102A1 EP 0677102 A1 EP0677102 A1 EP 0677102A1 EP 94900786 A EP94900786 A EP 94900786A EP 94900786 A EP94900786 A EP 94900786A EP 0677102 A1 EP0677102 A1 EP 0677102A1
Authority
EP
European Patent Office
Prior art keywords
peroxidase
group
hydrogen peroxide
enhancing agent
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.)
Withdrawn
Application number
EP94900786A
Other languages
German (de)
English (en)
Inventor
Palle Schneider
Morten Birket Andersen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novo Nordisk AS
Original Assignee
Novo Nordisk AS
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Novo Nordisk AS filed Critical Novo Nordisk AS
Publication of EP0677102A1 publication Critical patent/EP0677102A1/fr
Withdrawn legal-status Critical Current

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    • 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
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0065—Oxidoreductases (1.) acting on hydrogen peroxide as acceptor (1.11)
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0021—Dye-stain or dye-transfer inhibiting compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/18—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2041—Dihydric alcohols
    • C11D3/2058—Dihydric alcohols aromatic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2068—Ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2072—Aldehydes-ketones
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2086—Hydroxy carboxylic acids-salts thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/24—Organic compounds containing halogen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/30—Amines; Substituted amines ; Quaternized amines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • C11D3/38654—Preparations containing enzymes, e.g. protease or amylase containing oxidase or reductase
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2006—Monohydric alcohols
    • C11D3/2034—Monohydric alcohols aromatic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3418—Toluene -, xylene -, cumene -, benzene - or naphthalene sulfonates or sulfates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3463—Organic compounds containing sulfur containing thio sulfate or sulfite groups
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3472—Organic compounds containing sulfur additionally containing -COOH groups or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3481—Organic compounds containing sulfur containing sulfur in a heterocyclic ring, e.g. sultones or sulfolanes

Definitions

  • This invention relates to activation of enzymes. More specifically, the invention relates to peroxidase enhancing agents.
  • the invention also relates to methods of oxidizing a substrate with a source of hydrogen peroxide in the presence of a peroxidase enzyme and a peroxidase enhancing agent. More specifically, the invention relates to a method of bleaching of dye in solutions, to a method of inhibiting the transfer of a textile dye from a dyed fabric to another fabric when said fabrics are washed together in a wash liquor, to a method of bleaching of lignin-containing material, in particular bleach ⁇ ing of pulp for paper production, to a method of treatment of waste water from pulp manufacturing, and to a method of enzymatic polymerization and/or modification of lignin or lignin containing material.
  • Peroxidases are enzymes that catalyse the oxidation of a substrate (an electron or hydrogen donor) with hydrogen peroxide.
  • Such enzymes are known from microbial, plant and animal origins, e.g. peroxidase from Coprinus cinereus (cf. e.g. EP 179,486). They are typically hemopro- teins, i.e. they contain a heme as a prosthetic group.
  • Use of peroxidase together with hydrogen peroxide or a hydrogen peroxide precursor has been suggested e.g. in bleach ⁇ ing of pulp for paper production, in treatment of waste water from pulp production, for improved bleaching in laundry detergents, for dye transfer inhibition during laundering, and for lignin modification, e.g. in particle board production.
  • ABTS 2,2'-azino-bis(3-ethylbenzothiazoline-6- sulfonate)
  • Boehringer Mannheim supplied by Boehringer Mannheim, is a chromogenic substrate, and a common peroxidase and phenol oxidase assay agent.
  • These enzymes catalyse the oxidation of ABTS by hydrogen peroxide and dioxygen, respectively, producing a greenish-blue colour, which process may be monitored photo ⁇ metrically.
  • ABTS has been found to form a stable radical cation when oxidized by a laccase enzyme (polyphenol oxidase, EC 1.10.3.2), and has been proposed to act as a redox mediator for oxidation of non-phenolic lignin model compounds [Bourbonnais R, Paice M G; FEBS Lett (1990) 267 99-102].
  • a laccase enzyme polyphenol oxidase, EC 1.10.3.2
  • ABTS redox mediator for oxidation of non-phenolic lignin model compounds
  • oxidizable substrates e.g. metal ions and phenolic compounds such as 7-hydroxycoumarin (7HCm) , vanillin (VAN) , and p-hydroxybenzenesulfonate (pHBS)
  • accelerators or enhancers able to enhance bleaching reactions (cf. e.g. WO 92/18683, WO 92/18687, and Kato M and Shimizu S. Plant Cell Physiol. 1985 26 (7), pp. 1291-1301 (cf. Table 1 in particular) , or Saunders B C, et al., Peroxidase, London, 1964, p. 141 ff) .
  • the present invention provides an agent for enhancing the activity of a peroxidase enzyme, the agent being described by the general formula
  • the invention provides a method of inhibiting the transfer of a textile dye from a dyed fabric to another fabric when said fabrics are washed together in a wash liquor, the method comprising treatment of the wash liquor with a peroxidase enzyme in the presence of a source of hydrogen peroxide and in presence of a peroxidase enhancing agent of the invention.
  • the invention provides a detergent additive capable of inhibiting the transfer of a textile dye from a dyed fabric to another fabric when said fabrics are washed together in a wash liquor, the detergent additive comprising an enzyme exhibiting peroxidase activity, a source of hydrogen peroxide and a peroxidase enhancing agent of the invention.
  • the invention provides a detergent composition capable of inhibiting the transfer of a textile dye from a dyed fabric to another fabric when said fabrics are washed together in a wash liquor, the detergent composition comprising an enzyme exhibiting peroxidase ac ⁇ tivity, a source of hydrogen peroxide, and a peroxidase enhancing agent of the invention.
  • the invention provides a method of bleaching of lignin-containing material, in particular bleach- ing of pulp for paper production, the method comprising treatment of the lignin or lignin containing material with a peroxidase enzyme in the presence of a source of hydrogen peroxide and in the presence of a peroxidase enhancing agent of the invention.
  • the invention provides a method of enzymatic polymerization and/or modification of lignin or lignin containing material, the method comprising treatment of the lignin or lignin containing material with a peroxidase enzyme in the presence of a source of hydrogen peroxide and in presence of a peroxidase enhancing agent of the invention.
  • the invention provides a method of treatment of waste water, e.g. waste water from the chemical or pharmaceutical industry, the method comprising treatment of the waste water with a peroxidase enzyme in the presence of a source of hydrogen peroxide and in the presence of a peroxidase enhancing agent of the invention.
  • Fig. 1 shows the substituents II, III, IV, and V, of the general formula I according to the invention
  • Fig. 2 shows a comparison of a peroxidase enhancing agent of the invention (ABTS) and pHBS, applied to bleaching of Methyl Orange by a Coprinus cinereus peroxidase (1: pHBS, 20 ⁇ M H 2 0 2 ; 2 : pHBS , 200 ⁇ M H 2 0 2 ; 3 : ABTS , 20 ⁇ M H 2 0 2 ; 4 : ABTS , 200 ⁇ M H 2 0 2 ) ;
  • ABTS peroxidase enhancing agent of the invention
  • Fig. 3 shows accelerated bleaching of Methyl Orange by a Coprinus cinereus peroxidase in the presence of varying
  • ABTS (l: 0 ⁇ M ABTS; 2: 1 ⁇ M ABTS; 3: 5 ⁇ M ABTS; and 4: 10 ⁇ M
  • Fig. 4 shows a comparison of the initial bleaching rates during bleaching of Direct Blue 1 (DB1) at pH 10.5 (D ABTS, 1 10 nM peroxidase; ⁇ VAN, 100 nM peroxidase; ⁇ 7HCm, 100 nM peroxidase; A pHBS, 100 nM peroxidase) ; and
  • Fig. 5 shows a comparison of the initial bleaching rates during bleaching of DB1 at pH 8.8 (and pH 10.5) (D ABTS pH 8.8; ⁇ VAN pH 8.8; ⁇ 7HCm pH 8.8; 0 ABTS pH 10.5; and A pHBS pH 158.8) .
  • the present invention relates to the use of a known chemical compound for enhancing the activity of peroxidase 20 enzymes. Accordingly, the invention provides an agent capable of enhancing the effect of a peroxidase enzyme.
  • the agent is an azino compound described by the general formula I:
  • the peroxidase enhancing agent of the invention may be in free form or in the form of an addition salt.
  • the substituent groups R 1 , R 2 , R 3 , and R 4 which may be identical or different, independently represents hydrogen, halogen, a hydroxy group, a C.,-C 3 alkyl group, or a sulfo group.
  • the halogen is fluoro, chloro, or bromo.
  • the C 1 -C 3 alkyl group is methyl, ethyl, propyl, or isopropyl.
  • the substituent group R 5 represents halogen, a hydroxy group, a C,-C 3 alkoxy group, a C,- C 3 alkyl group, or an amino group.
  • a peroxidase enhancing agent of the invention is 2,2'-azino-bis(3-ethyl- benzothiazoline-6-sulfonate) .
  • This compound abbreviated ABTS, is a chromogenic substrate, and a common peroxidase and phenol oxidase assay agent.
  • ABTS contrary to the enhancers known and described above, is capable of acting as a peroxidase enhancing agent at highly alkaline conditions, i.e. above pH 9.
  • This feature allows ABTS to be implemented into e.g. detergent compositions, intended for performance in the range pH 7-13, particularly the range pH 8- 12, preferably the range pH 9-11.
  • the invention provides a method of oxidizing a substrate with a source of hydrogen peroxide in the presence of a peroxidase enzyme, the method being characterized by the presence of a peroxidase enhancing agent of the general formula
  • substituents the symbols A and B which may be identical or different, independently represents any of the substituents II, III, IV, and V, presented in Fig. 1; in which substituents the symbols X and Y, which may be identical or different, independently represents carbon, nitrogen, which nitrogen may be unsubstituted or substituted with a substituent group R 5 , sulfur, oxygen, selenium or tellurium; and in which substituents the substituent groups R 1 , R 2 , R 3 , and R 4 , which may be identical or different, independently represents hydrogen, halogen, a hydroxy group, a C ⁇ C j alkoxy group, a formyl group, a carboxy group, a sulfo group, a nitro group, a C,,-C 5 alkyl group, which alkyl group may furthermore be saturated or unsaturated, or an amino group, which amino group may furthermore be unsubstituted or substituted once or twice with a substituent group R 5 ; which substituent group
  • the peroxidase enhancing agent of the invention may be in free form or in the form of an addition salt.
  • the substituent groups R , R 2 , R 3 , and R 4 which may be identical or different, independently represents hydrogen, halogen, a hydroxy group, a C.,-C 3 alkyl group, or a sulfo group.
  • the halogen is fluoro, chloro, or bromo.
  • the C,-C 3 alkyl group is methyl, ethyl, propyl, or isopropyl.
  • the substituent group R 5 represents halogen, a hydroxy group, a C.-C 3 alkoxy group, a C,- C 3 alkyl group, or an amino group.
  • the peroxidase enhancing agent of the invention is 2,2'-azino-bis(3-ethyl- benzothiazoline-6-sulfonate) (ABTS) .
  • the enzyme employed in the method of the invention may be any peroxidase enzyme comprised by the enzyme classification EC 1.11.1.7. Such enzymes are known from microbial, plant and animal origins.
  • the peroxidase employed in the method of the invention is producible by plants (e.g. horseradish peroxidase) or microorganisms such as fungi or bacteria.
  • the peroxidase is derived from Coprinus. e.g. C. cinereus or C. macrorhizus. or from Bacillus, e.g. B. pumilus, particularly a peroxidase according to PCT/DK 90/00260.
  • the peroxidase may furthermore be one which is produc ⁇ ible by a method comprising cultivating a host cell transformed with a recombinant DNA vector which carries a DNA sequence encoding said peroxidase as well as DNA sequences encoding functions permitting the expression of the DNA sequence encoding the peroxidase, in a culture medium under conditions permitting the expression of the peroxidase and recovering the peroxidase from the culture.
  • a recombinantly produced peroxidase is a peroxidase derived from a Coprinus sp. , in particular Coprinus macrorhizus or cinereus according to WO 92/16634.
  • the peroxidase enhancing agent of the invention may be present in concentrations of from 0.01 to 100 ⁇ M, more prefer ⁇ red 0.1 to 50 ⁇ M, most preferred 1 to 10 ⁇ M.
  • the source of hydrogen peroxide may be hydrogen peroxide or a hydrogen peroxide precursor, e.g. percarbonate or per ⁇ borate, or a hydrogen peroxide generating enzyme system, e.g. an oxidase and a substrate for the oxidase.
  • Hydrogen peroxide may be added at the beginning or during the process, e.g. in an amount of 0.001-5 mM, particularly 0.01-1 mM.
  • Coprinus peroxidase 0.01-0.25 mM H 2 0 2 is preferred, and with B. pumilus peroxidase 0.1-1 mM H 2 0 2 .
  • Methods according to the invention of oxidizing a substrate with a source of hydrogen peroxide in the presence of a peroxidase enzyme find various industrial applications.
  • the method of the invention finds application for bleaching of dye in solutions.
  • the method of the invention finds application for dye transfer inhibition, e.g. for treatment of dyed textiles (cf. e.g. WO 92/18687) or during laundering (cf. e.g. WO 91/05839) .
  • the invention provides a method for inhibiting the transfer of a textile dye from a dyed fabric to another fabric when said fabrics are washed together in a wash liquor, the method comprising treatment of the wash liquor with a peroxidase enzyme in the presence of a source of hydrogen peroxide, and the presence of a peroxidase enhancing agent of the invention.
  • the textile dye may be a synthetic dye such as an azo dye, or a natural or na ⁇ ture-identical dye.
  • the method of the invention finds application in bleaching of pulp for paper production.
  • the use of a peroxidase together with hydrogen peroxide or a hydrogen peroxide precursor in bleaching of paper pulp has been de ⁇ scribed in e.g. SE 88/0673 and US 4,690,895.
  • the invention provides a method for bleaching of lignin-containing material, in particular bleach ⁇ ing of pulp for paper production, which method comprises treatment of the lignin or lignin containing material with a peroxidase enzyme in the presence of a source of hydrogen peroxide and in the presence of a peroxidase enhancing agent of the invention.
  • the method of the invention finds application for lignin modification, e.g. in particle board production.
  • Binders for producing wood composites such as fibre boards and particle boards can be made from peroxidase treated lignin (cf. US 4,432,921).
  • the invention provides a method for enzymatic polymerization and/or modification of lignin or lignin containing material, which method comprises treatment of the lignin or lignin containing material with a peroxidase enzyme in the presence of a source of hydrogen peroxide, and the presence of a peroxidase enhancing agent of the invention.
  • the method of the invention finds application in treatment of waste water e.g. waste water from the chemical or pharmaceutical industry, from dye manufac ⁇ turing, from the textile industry, or from pulp production (cf. e.g. US 4,623,465, or JP-A 2-31887).
  • the invention provides a method for treatment of waste water from dye manufacturing, from textile industry, or from pulp manufacturing, the method comprising treatment of the waste water with a peroxidase enzyme in the presence of a source of hydrogen peroxide and in the presence of a peroxidase enhancing agent of the invention.
  • the peroxidase enhancing agent may be added as a component of a detergent composition.
  • the invention provides a detergent additive capable of inhibiting the transfer of a textile dye from a dyed fabric to another fabric when said fabrics are washed together in a wash liquor, the detergent additive comprising an enzyme exhibiting peroxidase activity, a source of hydrogen peroxide, and a peroxidase enhancing agent of the invention.
  • the detergent additive may additionally comprise one or more other enzymes conventionally used in detergents, such as proteases, Upases, amylases, or cellulases.
  • the detergent additive is provided in the form of a granulate, preferably a non-dusting granulate, a liquid, in particular a stabilized liquid, a slurry, or in a protected form.
  • the invention provides a detergent composition capable of inhibiting the transfer of a textile dye from a dyed fabric to another fabric when said fabrics are washed together in a wash liquor, the detergent composition comprising an enzyme exhibiting peroxidase ac ⁇ tivity, a source of hydrogen peroxide and a peroxidase enhanc ⁇ ing agent of the invention.
  • the peroxidase enhancing agent of the invention may be included in the detergent as a part of a peroxidase system, comprising a peroxidase enzyme, a source of hydrogen peroxide, and the peroxidase enhancing agent of the invention.
  • the peroxidase system may be included in the detergent composition in the form of a non-dusting granulate, a liquid, in particular a stabilized liquid, or in a protected form.
  • Non- dusting granulates may be produced, e.g. as disclosed in US 4,106,991 and 4,661,452 (both to Novo Industri A/S) and may optionally be coated by methods known in the art.
  • Liquid enzyme preparations may, for instance, be stabilized by adding a polyol such as propylene glycol, a sugar or sugar alcohol, lactic acid or boric acid according to established methods. Other enzyme stabilizers are well known in the art.
  • a protected form of the peroxidase system may be prepared according to the method disclosed in EP 238,216.
  • the detergent composition of the invention may be in any convenient form, e.g. as powder, granules or liquid.
  • a liquid detergent may be aqueous, typically containing up to 90% water and 0-20% organic solvent.
  • the detergent composition comprises surfactants which may be anionic, nonionic, cationic, amphoteric or a mixture of these types.
  • the detergent will usually contain 0-50% anionic surfactant such as linear alkylbenzenesulfonate (LAS) , alpha- olefinsulfonate (AOS) , alkyl sulfate (AS) , alcohol ether sulfate (AES) or soap. It may also contain 0-40% nonionic surfactant such as nonyl phenol ethoxylate or alcohol ethoxy- late. Furthermore, it may contain a polyhydroxy fatty acid amide surfactant (e.g. as described in WO 92/06154) .
  • the pH (measured in aqueous detergent solution) will usually be neutral or alkaline, e.g. 7-11.
  • the detergent may contain 1-40% of a detergent builder such as zeolite, phosphate, phosphonate, citrate, NTA, EDTA or DTPA, alkenyl succinic anhydride, or silicate, or it may be unbuilt (i.e. essentially free of a detergent builder). It may also contain other conventional detergent ingredients, e.g. fabric conditioners, foam boosters, bleaching agents, e.g.
  • the detergent composition may additionally comprise one or more other enzymes conventionally used in detergents such as proteases, lipases, amylases, and cellulases.
  • a detergent composition formulated as a nonaqueous detergent liquid comprising a liquid nonionic surfactant consisting essentially of linear alkoxylated primary alcohol, phosphate builder, alkali, with a pH in use adjusted to a value between about 7 and 10.5.
  • a liquid compact detergent comprising 5-65% by weight of surfactant, 0-50% by weight of builder and 0-30% by weight of electrolyte.
  • Methyl Orange (Merck) catalysed by a recombinantly produced Coprinus cinereus peroxidase (rCiP) , obtained according to WO 92/16634, and hydrogen peroxide in the presence of 2,2'-azino-bis(3-ethylb- enzothiazoline-6-sulfonate) (ABTS, supplied by Boehringer Mannheim) or para-hydroxybenzene sulfonate (pHBS, supplied by Sigma) is shown in Fig. 2. The following conditions were used:
  • Reagents were mixed in a 1 cm cuvette, and the bleaching was started by addition of hydrogen peroxide.
  • the bleaching was detected spectrophotometrically at 465 nm, which is the ab ⁇ sorption peak of this dye. Bleaching was followed with respect to time over a span of 10 in.
  • Methyl Orange Accelerated bleaching of Methyl Orange (Merck) catalysed by a recombinantly produced Coprinus cinereus peroxidase (rCiP) , obtained according to WO 92/16634, and hydrogen peroxide in the presence of varying concentrations of 2,2'- azino-bis(3-ethylbenzothiazoline-6-sulfonate) (ABTS, supplied by Boehringer Mannheim) is shown in Fig. 3. The following conditions were used:
  • Reagents were mixed in a 1 cm cuvette, and the bleaching was started by addition of hydrogen peroxide.
  • the bleaching was detected spectrophotometrically at 610 nm, which is the ab ⁇ sorption peak of this dye. Bleaching was followed for 10 minutes, and the bleaching rates (- ⁇ mAbs/min) were determined from the initial (linear) reduction in absorbance.
  • the detergent solution for the washing trial was made up using 4.5 g/1 of a commercially available European high-pH powder detergent containing no bleach and no optical bright- ener.
  • the water used was tap water mixed with demineralized water in the ratio 1:2; the mixture had a hardness equivalent to approx. 1.1 mM Ca 2+ .
  • Textile load Approx. 6 g nylon dyed with acid Red 151 and 1 g white cotton per litre washing liquor
  • Peroxidase Recombinantly produced Coprinus cinereus peroxidase, obtained ac ⁇ cording to WO 92/16634, at 5 nM
  • test pieces were rinsed thoroughly in cold tap water and dried in the dark overnight, after which the remission measurements were performed. Treatments with various concentrations of the two enhancers yielded the following results:
  • the peroxidase system with 1 ⁇ M enhancer provided no significant dye transfer inhibition (reference without peroxidase system not included here) .
  • the ABTS system has an effect already at 5 ⁇ M of enhan ⁇ cer, whereas the pHBS system does not; and at 20 ⁇ M enhancer, the ABTS system has a much larger effect than the pHBS system.

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Abstract

L'invention concerne l'activation d'enzymes, et plus spécialement des agents de renfort de peroxydase. L'invention concerne également des procédés d'oxydation d'un substrat à l'aide d'une source d'eau oxygénée en présence d'une enzyme peroxydasique et d'un agent de renfort de peroxydase. Plus précisément, l'invention concerne un procédé de blanchiment d'un colorant dans une solution, un procédé d'inhibition du transfert d'un colorant pour textiles d'un tissu coloré à un autre tissu lors du lavage de ces tissus dans un même liquide de lavage, un procédé de blanchiment d'une matière renfermant de la lignine, notamment de blanchiment de pâte destinée à la fabrication du papier, un procédé de traitement des eaux usées provenant de la fabrication de pâte, ainsi qu'un procédé de modification et/ou de polymérisation enzymatique de la lignine ou d'une matière renfermant de la lignine.
EP94900786A 1992-12-01 1993-12-01 Amelioration de reactions enzymatiques Withdrawn EP0677102A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DK921441A DK144192D0 (da) 1992-12-01 1992-12-01 Aktivering af enzymer
DK1441/92 1993-10-26
PCT/DK1993/000394 WO1994012620A1 (fr) 1992-12-01 1993-12-01 Amelioration de reactions enzymatiques

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EP0677102A1 true EP0677102A1 (fr) 1995-10-18

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EP (1) EP0677102A1 (fr)
JP (1) JPH08503371A (fr)
BR (1) BR9307575A (fr)
CA (1) CA2150563A1 (fr)
DK (1) DK144192D0 (fr)
FI (1) FI952647A (fr)
WO (1) WO1994012620A1 (fr)

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* Cited by examiner, † Cited by third party
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WO2012001145A1 (fr) 2010-07-01 2012-01-05 Novozymes A/S Blanchiment de pâte
WO2012038466A1 (fr) 2010-09-21 2012-03-29 Novozymes A/S Élimination de sélénocyanate ou de sélénite de solutions aqueuses
WO2012149192A1 (fr) 2011-04-28 2012-11-01 Novozymes, Inc. Polypeptides à activité endoglucanase et polynucléotides codant pour les polypeptides
WO2013036898A2 (fr) 2011-09-09 2013-03-14 Novozymes A/S Amélioration des propriétés de matières papiers
EP2740840A1 (fr) 2012-12-07 2014-06-11 Novozymes A/S Amélioration de drainage de pâte à papier
WO2014090940A1 (fr) 2012-12-14 2014-06-19 Novozymes A/S Élimination de souillures issues de la peau
WO2019035038A1 (fr) 2017-08-18 2019-02-21 The Procter & Gamble Company Agent de nettoyage
WO2019035044A1 (fr) 2017-08-18 2019-02-21 The Procter & Gamble Company Procédé de nettoyage
WO2019035037A1 (fr) 2017-08-18 2019-02-21 The Procter & Gamble Company Kit de nettoyage
WO2019229228A1 (fr) 2018-05-31 2019-12-05 Novozymes A/S Procédé de traitement de pâte de cellulose à dissoudre à l'aide d'une monooxygénase polysaccharidique lytique
WO2021018751A1 (fr) 2019-07-26 2021-02-04 Novozymes A/S Traitement enzymatique de la pulpe de papier

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DK144392D0 (da) * 1992-12-01 1992-12-01 Novo Nordisk As Aktivering af enzymer
CA2115881C (fr) * 1993-02-25 2000-05-23 Michael G. Paice Methode de blanchiment sans chlore de la pate kraft
US5451337A (en) * 1994-05-31 1995-09-19 The Procter & Gamble Co. Dye transfer inhibition system containing a peroxidase/accelerator system
WO1997006244A1 (fr) * 1995-08-08 1997-02-20 Ciba Specialty Chemicals Holding Inc. Procede pour stimuler l'activite d'une enzyme, composes presentant une stimulation de l'activite de l'enzyme, et detergents contenant de tels composes
DE69737828T2 (de) * 1996-04-29 2008-03-06 Novozymes A/S Flüssige, nichtwässrige enzyme enthaltende zusammensetzungen
CA2270339A1 (fr) * 1996-11-25 1998-06-04 Unilever Plc Procede d'oxydation enzymatique
DE19713852A1 (de) 1997-04-04 1998-10-08 Henkel Kgaa Aktivatoren für Persauerstoffverbindungen in Wasch- und Reinigungsmitteln
CA2293698A1 (fr) 1997-06-10 1998-12-17 Unilever Plc Procede pour ameliorer l'activite d'une enzyme, composition de blanchiment, composition detergente et procede pour inhiber le transfert de colorant
EP1015544B1 (fr) 1997-09-08 2001-10-24 Unilever N.V. Procede servant a augmenter l'activite d'une enzyme
DE19756172A1 (de) * 1997-12-17 1999-06-24 Stockhausen Chem Fab Gmbh Verfahren zur Pfropfung von Lignin, danach hergestellte Polymerisate und deren Verwendung
US6592867B2 (en) * 1998-11-09 2003-07-15 Novozymes A/S Antimicrobial composition containing an oxidoreductase and an enhancer of the N-hydroxyanilide-type
US6610172B1 (en) 1999-05-06 2003-08-26 Novozymes A/S Process for treating pulp with laccase and a mediator to increase paper wet strength
WO2001000768A1 (fr) 1999-06-23 2001-01-04 Unilever N.V. Compositions de detergents de blanchiment
BR0011820A (pt) * 1999-06-23 2002-03-19 Unilever Nv Processo para o aumento da atividade de uma enzima de oxidação de fenol,composição enzimática de branqueamento,composição detergente de branqueamento,e,processo para remoção de manchas coloridas de tecidos em processo de lavagem
WO2001010195A1 (fr) * 1999-08-10 2001-02-15 Novozymes A/S Reduction des mauvaises odeurs dans une litiere pour animaux souillee
WO2001034750A1 (fr) * 1999-11-11 2001-05-17 Unilever N.V. Methode et composition destinees a renforcer l'activite d'une enzyme
AU1143601A (en) 1999-11-11 2001-06-06 Convents, Daniel Method and composition for enhancing the activity of an enzyme
WO2001092454A1 (fr) * 2000-05-31 2001-12-06 Unilever N.V. Composition et procede d'oxydation enzymatique
CN1473190A (zh) 2000-10-31 2004-02-04 氧化方法和组合物
GB0030673D0 (en) 2000-12-15 2001-01-31 Unilever Plc Ligand and complex for catalytically bleaching a substrate
GB0030877D0 (en) 2000-12-18 2001-01-31 Unilever Plc Enhancement of air bleaching catalysts
GB0222501D0 (en) 2002-09-27 2002-11-06 Unilever Plc Composition and method for bleaching a substrate
DE102004020355A1 (de) * 2004-04-26 2005-11-10 Call, Krimhild Oxidative, reduktive, hydrolytische und andere enzymatische Systeme zur Oxidation, Reduktion, zum Coaten, Koppeln und Crosslinken von natürlichen und künstlichen Faserstoffen, Kunststoffen oder anderen natürlichen und künstlichen Mono- bis Polymerstoffen
JP5311662B2 (ja) * 2009-08-24 2013-10-09 キッコーマン株式会社 ペルオキシダーゼ化学発光反応の発光増強方法及びペルオキシダーゼ化学発光反応用発光増強剤
BR112014006807B1 (pt) 2011-09-23 2021-11-09 Novozymes A/S Método para modificação de cor de têxtil
WO2018012606A1 (fr) * 2016-07-13 2018-01-18 キッコーマン株式会社 Accélérateur de réaction
EP4053328A1 (fr) 2021-03-02 2022-09-07 CHT Germany GmbH Traitement combiné de blanchiment pour textiles

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012001145A1 (fr) 2010-07-01 2012-01-05 Novozymes A/S Blanchiment de pâte
WO2012038466A1 (fr) 2010-09-21 2012-03-29 Novozymes A/S Élimination de sélénocyanate ou de sélénite de solutions aqueuses
WO2012149192A1 (fr) 2011-04-28 2012-11-01 Novozymes, Inc. Polypeptides à activité endoglucanase et polynucléotides codant pour les polypeptides
WO2013036898A2 (fr) 2011-09-09 2013-03-14 Novozymes A/S Amélioration des propriétés de matières papiers
EP2740840A1 (fr) 2012-12-07 2014-06-11 Novozymes A/S Amélioration de drainage de pâte à papier
WO2014086976A1 (fr) 2012-12-07 2014-06-12 Novozymes A/S Amélioration de l'égouttage de pâte à papier
WO2014090940A1 (fr) 2012-12-14 2014-06-19 Novozymes A/S Élimination de souillures issues de la peau
WO2019035038A1 (fr) 2017-08-18 2019-02-21 The Procter & Gamble Company Agent de nettoyage
WO2019035044A1 (fr) 2017-08-18 2019-02-21 The Procter & Gamble Company Procédé de nettoyage
WO2019035037A1 (fr) 2017-08-18 2019-02-21 The Procter & Gamble Company Kit de nettoyage
WO2019229228A1 (fr) 2018-05-31 2019-12-05 Novozymes A/S Procédé de traitement de pâte de cellulose à dissoudre à l'aide d'une monooxygénase polysaccharidique lytique
WO2021018751A1 (fr) 2019-07-26 2021-02-04 Novozymes A/S Traitement enzymatique de la pulpe de papier

Also Published As

Publication number Publication date
FI952647A0 (fi) 1995-05-31
CA2150563A1 (fr) 1994-06-09
JPH08503371A (ja) 1996-04-16
FI952647A (fi) 1995-05-31
BR9307575A (pt) 1999-06-15
WO1994012620A1 (fr) 1994-06-09
DK144192D0 (da) 1992-12-01

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