Modification of polysaccharides by means of a phenol oxidizing enzyme

• US 6,660,503 B2
• Filed: 07/11/2001
• Issued: 12/09/2003
• Est. Priority Date: 12/19/1997
• Status: Expired due to Fees

• Current Assignee: Novozymes A/S (Novozymes)
• Original Assignee: Novozymes A/S (Novozymes)
• Inventors: Kierulff, Jesper Vallentin
• Primary Examiner(s): PRATS, FRANCISCO CHANDLER
• Application Number:
  US09/903,186
• Publication Number:
  US 20010055794A1
• Time in Patent Office: 881 Days
• Field of Search: 435/101, 435/72, 435/136, 435/142, 435/189, 435/190
• US Class Current: 435/101
• CPC Class Codes: C08B 15/04 Carboxycellulose, e.g. prepared by oxidation with nitrogen dioxide
• CPC Class Codes: C08B 31/18 Oxidised starch
• CPC Class Codes: C08B 37/00 Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof cellulose D21; microbiological processes C12P
• CPC Class Codes: C12P 19/02 Monosaccharides 2-ketogulonic acid C12P7/60
• CPC Class Codes: C12P 19/04 Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
• CPC Class Codes: D06M 13/322 with compounds containing nitrogen
• CPC Class Codes: D06M 13/338 Organic hydrazines; Hydrazinium compounds
• CPC Class Codes: D06M 13/35 Heterocyclic compounds
• CPC Class Codes: D06M 13/352 having five-membered heterocyclic rings
• CPC Class Codes: D06M 16/003 with enzymes or microorganisms

Abstract

The present invention deals with a process for oxidation of a hydroxy group of C₁ and/or C₂ and/or C₃ and/or C₄ and/or C₅ and/or C₆ of a sugar monomer of an oligo- or a polysaccharide comprising contacting, in an aqueous medium, the oligo- or the polysaccharide with a phenol oxidizing enzyme and an enhancing agent, whereby an oligo- or a polysaccharide with altered characteristics compared to the native oligo- or polysaccharide is created.

Claims

1. A process for oxidation of a cellulose material, wherein the cellulose material is selected from the group consisting of a stable fiber, a thread, a yarn, or a fabric comprising contacting, in an aqueous medium comprising an enhancing agent selected from the group consisting of N-hydroxybenzotraizole, violuric acid, N-hydroxyacetanilide and TEMPO, the cellulose material with a laccase, under conditions in which the oxidation results in the formation of a carbonyl or a carboxylate group.

2. The process of claim 1, wherein the aqueous medium further comprises an enhancing agent which enhances the activity of the laccase.

3. The process of claim 1, wherein the laccase is obtained from Trametes, Coprinus or Myceliophthora.

4. A process for oxidation of a cellulose or cellulose derivative containing material, wherein the material is selected from the group consisting of a stable fiber, a thread, a yarn, or a fabric, comprising contacting, in an aqueous medium, the cellulose or cellulose derivative containing material with a peroxidase and a hydrogen peroxide source, under conditions which the oxidation results in the formation of a carbonyl or a carboxylate group wherein the aqueous medium further comprises an enhancing agent which enhances the activity of the peroxidase, wherein the enhancing agent is selected from the group consisting of aliphatic, cycloaliphatic, heterocyclic or aromatic compounds containing NO—

, N(OH)—

, N(OH)R, the corresponding N-oxyl free radicals thereof, a compound of formula;

wherein R¹, R², R³, R⁴ are individually selected from the group consisting of hydrogen, halogen, hydroxy, formyl, carboxy and salts and esters thereof, amino, nitro, C₁-C₁₂, alkyl, C₁-C₁₂ alkoxy, carbonyl(C₁-C₁₂ alkyl), aryl, wherein the R¹, R², R³, R⁴ may be substituted with R⁵, wherein R⁵ represents hydrogen, halogen, hydroxy, formyl, carboxy and salts and esters thereof, amino, nitro, C₁-C₁₂ alkyl, C₁-C₆ alkoxy, carbonyl(C₁-C₁₂ alkyl), aryl, [X] represents a group from (—

N=N—

), (—

N═

CR⁶)_m, (—

CR⁶═

N—

)_m, (—

CR⁷═

CR⁸)_m, and m is 1 or 2, N-hydroxybenzotriazole, violuric acid, N-hydroxyacetanilide and TEMPO (2,2,6,6-tetramethylpiperidinoxyl).

5. The process of claim 4, wherein the peroxidase is horseradish peroxidase, soybean peroxidase, or a peroxidase enzyme obtained from Coprinus, Bacillus or Myxococcus.

6. The process of claim 4, wherein the hydrogen peroxide source is hydrogen peroxide, a hydrogen peroxide precursor, a hydrogen peroxide generating enzyme system, or a peroxycarboxylic acid or a salt thereof.

7. The process according to claim 4, wherein the enhancing agent is a compound of formula:

wherein R¹, R², R³, R⁴ are individually selected from the group consisting of hydrogen, halogen, hydroxy, formyl, carboxy and salts and esters thereof, amino, nitro, C₁-C₁₂ alkyl, C₁-C₆ alkoxy, carbonyl(C₁-C₁₂ alkyl), aryl, wherein the R¹, R², R³, R⁴ may be substituted with R⁵, wherein R⁵ represents hydrogen, halogen, hydroxy, formyl, carboxy and salts and esters thereof, amino, nitro, C₁-C₁₂ alkyl, C₁-C₆ alkoxy, carbonyl(C₁-C₁₂ alkyl), aryl.

8. The process according to claim 4, wherein R¹, R², R³, R⁴, R⁵ represent phenyl, sulfo, aminosulfonyl, carbamoyl, phosphono, phosphonooxy, and salts and esters thereof.