KR870006073A - 키틴의 부분가수분해에 의한 수용성기틴올리고머의 제조방법 - Google Patents
키틴의 부분가수분해에 의한 수용성기틴올리고머의 제조방법 Download PDFInfo
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- KR870006073A KR870006073A KR860010582A KR860010582A KR870006073A KR 870006073 A KR870006073 A KR 870006073A KR 860010582 A KR860010582 A KR 860010582A KR 860010582 A KR860010582 A KR 860010582A KR 870006073 A KR870006073 A KR 870006073A
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- KR
- South Korea
- Prior art keywords
- acetyl
- chitin
- penta
- tetra
- chitohexaose
- Prior art date
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- 229920002101 Chitin Polymers 0.000 title claims 20
- 238000006460 hydrolysis reaction Methods 0.000 title claims 7
- 238000000034 method Methods 0.000 title claims 5
- 230000007062 hydrolysis Effects 0.000 title claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 23
- FUHDMRPNDKDRFE-LPUYKFNUSA-N n-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r)-5-acetamido-1,2,4-trihydroxy-6-oxohexan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy- Chemical compound O[C@@H]1[C@@H](NC(C)=O)[C@H](O[C@@H]([C@H](O)[C@H](C=O)NC(=O)C)[C@H](O)CO)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)NC(C)=O)[C@@H](CO)O3)NC(C)=O)[C@@H](CO)O2)NC(C)=O)[C@@H](CO)O1 FUHDMRPNDKDRFE-LPUYKFNUSA-N 0.000 claims 10
- PFZKWTWCVGDJQC-VNVOTFTJSA-N N,N',N'',N'''-tetraacetylchitotetraose Chemical compound O[C@@H]1[C@@H](NC(=O)C)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)NC(C)=O)[C@@H](CO)O2)NC(C)=O)[C@@H](CO)O1 PFZKWTWCVGDJQC-VNVOTFTJSA-N 0.000 claims 8
- 239000011541 reaction mixture Substances 0.000 claims 8
- DPTYILOGADPXRZ-RXDSZOQSSA-N Penta-N-acetylchitopentaose Chemical compound O[C@@H]1[C@@H](NC(C)=O)[C@H](O[C@@H]([C@H](O)[C@H](C=O)NC(=O)C)[C@H](O)CO)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)NC(C)=O)[C@@H](CO)O2)NC(C)=O)[C@@H](CO)O1 DPTYILOGADPXRZ-RXDSZOQSSA-N 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 4
- 238000002156 mixing Methods 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims 3
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims 3
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 229950006780 n-acetylglucosamine Drugs 0.000 claims 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 239000012141 concentrate Substances 0.000 claims 2
- 239000000706 filtrate Substances 0.000 claims 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 2
- 239000012433 hydrogen halide Substances 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 230000007935 neutral effect Effects 0.000 claims 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- 239000008247 solid mixture Substances 0.000 claims 2
- 238000009987 spinning Methods 0.000 claims 2
- PLJAKLUDUPBLGD-VLWZLFBZSA-N N-acetyl-beta-D-glucosaminyl-(1->4)-N-acetyl-aldehydo-D-glucosamine Chemical compound CC(=O)N[C@@H](C=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]1NC(C)=O PLJAKLUDUPBLGD-VLWZLFBZSA-N 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
- LRDDKCYRFNJZBX-WHFMPQCRSA-N Tri-N-acetylchitotriose Chemical compound O[C@@H]1[C@@H](NC(C)=O)[C@H](O[C@@H]([C@H](O)[C@H](C=O)NC(=O)C)[C@H](O)CO)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 LRDDKCYRFNJZBX-WHFMPQCRSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000011033 desalting Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 claims 1
- 239000008240 homogeneous mixture Substances 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- UKZKHAFAYSQVFL-MBGZTGDNSA-N n-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(2r,3s,4r,5r)-5-acetamido-1,2,4-trihydroxy-6-oxohexan-3-yl]oxy-4-hydroxy Chemical compound O[C@@H]1[C@@H](NC(C)=O)[C@H](O[C@@H]([C@H](O)[C@H](C=O)NC(=O)C)[C@H](O)CO)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O[C@H]4[C@@H]([C@@H](O)[C@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)NC(C)=O)[C@@H](CO)O4)NC(C)=O)[C@@H](CO)O3)NC(C)=O)[C@@H](CO)O2)NC(C)=O)[C@@H](CO)O1 UKZKHAFAYSQVFL-MBGZTGDNSA-N 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 238000000527 sonication Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- Materials Engineering (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- [일반식](식중, n-은 테트라-N-아세틸-키토테트라오스에서는 2이고, 펜타-N-아세틸-티토펜타오스에서는 3이고, 헥사-N-아세틸-키토헥사오스에서는 4이다)로 표시되는 키틴올리고머 중 테트라-N-아세틸-키토테트라오스, 펜타-N-아세틸-키토펜타오스 및 헥사-N-아세틸-키토헥사오스의 제조방법에 있어서, 초음파방사 및 기계적교반기에 의한 혼합을 행하면서 초기에 장입된 키틴 100g당 할로겐화수소 1.5몰 내지 6몰을 포함하는 일정량의 진한 할로겐화수소산에 미분키틴을 한번에 첨가하여 미분키틴과 진한 할로겐화 수소산의 균일한 혼합물을 형성시킨 후에,키틴과 진한 할로겐화 수소산으로 이루어진 균일한 반응혼합물을 계속해서 초음파방사 및 기계적교반기에 의한 혼합을 행하면서 키틴을 진한 할로겐화수소산으로 가수분해 하는 것을 특징으로 하는 테트라-N-아세틸-키토테트라오스, 펜타-N-아세틸-키토펜타오스 및 헥사-N-아세틸-키토헥사오스의 제조방법.
- 제 1 항에 있어서, (ⅰ) 초음파방사 및 기계적교반기에 의한 혼합을 행하면서 초기에 장입한 키틴 100g당 할로겐화수소 1.5몰 내지 6몰을 포함하는 일정량의 진한 할로겐화수소산에 미분키틴을 한번에 첨가하여 미분키틴과 진한 할로겐화수소산의 균일한 혼합물을 형성시키는 공정과, (ⅱ) 키틴과 진한 할로겐화수소산으로 이루어진 균일한 반응혼합물을 계속해서 초음파방사 및 기계적반기에 의한 혼합을 행하면서 키틴을 진한 할로겐화수소산으로 가수분해하는 공정과, (ⅲ) 초음파방사 및 기계적교반기에 의한 혼합을 행하면서 수용성인 N-아세틸-글로코사민, 디-N-아세틸-키토비오스, 트리-N-아세틸-키토트리오스, 테트라-N-아세틸-키토테트라오스, 펜타-N-아세틸-키토펜타오스, 헥사-N-아세틸-키토헥사오스 및 헵타-N-아세틸-키토헵타오스의 형성과 더불어 장입된 키틴의 40중량% 이상이 가수분해에 의해 해중합되어 수용액상의 반응혼합물에 용해되는 공정과, (ⅳ) 가수분해된 수용액상의 반응혼합물로부터 혼합물 또는 단독으로 테트라-N-아세틸-키토테트라오스, 펜타-N-아세틸-키토펜타오스 및 펜타-N-아세틸-키토펜타오스를 회수하는 공정으로 이루어지는 것을 특징으로 하는 테트라-N-아세틸-키토테트라오스, 펜타-N-아세틸-키토펜타오스 및 헥사-N-아세틸-키토헥사오스의 제조방법.
- 제 1 항에 또는 제 2 항에 있어서, 할로겐화수소산은 10N 내지 12N의 염산을 사용하는 한편 키틴은 10N 내지 12N 농도의 염화수소를 포함하는 농염산으로 35℃ 내지 40℃의 온도에서 대략 2시간 내지 3시간 동안 가수분해 하는 것을 특징으로 하는 테트라-N-아세틸-키토테트라우스, 펜타-N-아세틸-키토펜타오스 및 헥사-N-아세틸-키토헥사오스의 제조방법.
- 제 1 항에 또는 제 2 항에 있어서, 키틴과 농염산으로 이루어지는 혼합물을 계속해서 주파수가 10KHz 내지 200KHz인 초음파로 방사함과 동시에 기계적교반기에 의해 혼합하는 것을 특징으로 하는 테트라-N-아세틸-키토테트라오스, 펜타-N-아세틸-키토펜타오스 및 헥사-N-아세틸-키토헥사오스의 제조방법.
- 제 1 항에 또는 제 2 항에 있어서, 키틴의 가수분해 반응은 초음파방사 및 기계적혼합하에서 초기에 장입된 키틴의 40중량% 내지 80중량%가 가수분해에 의해 해중합되어 액상의 반응혼합물에 용해될 때 까지 행하는 것을 특징으로 하는 테트라-N-아세틸-키토테트라오스, 펜타-N-아세틸-키토펜타오스 및 헥사-N-아세틸-키토헥사오스의 제조방법.
- 제 2 항에 있어서, 사용된 산은 농염산인 한편 가수분해된 액상의 반응혼합물로부터 테트라-N-아세틸-키토테트라오스, 펜타-N-아세틸-키토펜타오스 및 헥사-N-아세틸-키토헥사오스의 회수공정은(a) 가수분해반응 종료후의 가수분해반응 혼합물 전체를 수산화나트륨수용액, 수산화 칼륨수용액, 탄산나트륨수용액, 탄산칼륨수용액, 중탄산나트륨 수용액 또는 중탄산칼륨수용액으로 중화하고, (b) 중화된 반응혼합물을 여과하여 불용성 잔여물을 제거한 다음 형성된 N-아세틸글루코사민, 수용성키틴올리고머 및 염화나트륨을 포함하는 중성여액을 얻고, (c) 중성여액을 탈염한 후, (d) N-아세틸글루코사민과 수용성 키틴올리고머를 포함하는 탈염수용액을 농축 또는 건조시켜서 N-아세틸글루코사민과 수용성 키틴올리고머를 포함하는 농축액 또는 고상혼합물을 얻고, (e) 얻어진 농축액 또는 고상 혼합물을 겔여과제가 든 컬럼 또는 고압액체 크로마토그래피 등으로 크로마토그래피하여 혼합물 또는 단독으로 테트라-N-아세틸-키토테트라오스, 펜타-N-아세틸-키토펜타오스 및 헥사-N-아세틸-키토헥사오스를 얻는 것을 특징으로 하는 테트라-N-아세틸-키토테트라오스, 펜타-N-아세틸-키토펜타오스 및 헥사-N-아세틸-키토헥사오스의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60-278688 | 1985-12-11 | ||
| JP278688 | 1985-12-11 | ||
| JP60278688A JPS62138496A (ja) | 1985-12-11 | 1985-12-11 | キチンオリゴマ−の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR870006073A true KR870006073A (ko) | 1987-07-09 |
| KR900002853B1 KR900002853B1 (ko) | 1990-05-01 |
Family
ID=17600786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019860010582A KR900002853B1 (ko) | 1985-12-11 | 1986-12-11 | 키틴의 부분 가수 분해에 의한 수용성기틴올리고머의 제조방법 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4804750A (ko) |
| EP (1) | EP0226452B1 (ko) |
| JP (1) | JPS62138496A (ko) |
| KR (1) | KR900002853B1 (ko) |
| CA (1) | CA1297832C (ko) |
| DE (1) | DE3687142T2 (ko) |
| DK (1) | DK592886A (ko) |
| ES (1) | ES2043604T3 (ko) |
| FI (1) | FI80713C (ko) |
| NO (1) | NO167747C (ko) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5010181A (en) * | 1988-03-28 | 1991-04-23 | Coughlin Robert W | Partially treated shellfish waste for removal of heavy metals from aqueous solution |
| ATE123414T1 (de) * | 1989-01-23 | 1995-06-15 | Akzo Nobel Nv | Ortspezifische in-vivo-aktivierung von therapeutischen arzneimitteln. |
| US5433955A (en) * | 1989-01-23 | 1995-07-18 | Akzo N.V. | Site specific in vivo activation of therapeutic drugs |
| JP2871822B2 (ja) * | 1989-08-29 | 1999-03-17 | 玉造株式会社 | 末端に２，５―アンヒドロマンニトール基または２，５―アンヒドロマンノース基を有するキチン・キトサンオリゴマーおよびその製造方法 |
| FR2701030B1 (fr) * | 1993-01-20 | 1995-04-07 | Aber Technologies | Procédé pour l'hydrolyse de chitine et/ou de chitosane et oligomères de chlorhydrate de D-glucosamine obtenus. |
| US5334388A (en) * | 1993-09-15 | 1994-08-02 | Becton, Dickinson And Company | Antimicrobial drying substrate |
| CA2180826A1 (en) | 1994-01-13 | 1995-07-20 | Richard J. Ii Stoner | Organic disease control system |
| US6060429A (en) * | 1994-07-25 | 2000-05-09 | State of Israel--Ministry of Agriculture | Composition and method for controlling plant diseases caused by fungi |
| US5705634A (en) * | 1995-03-02 | 1998-01-06 | Perimmune Holdings, Inc. | High yield preparation of dimeric to decameric chitin oligomers |
| US5891861A (en) * | 1996-10-15 | 1999-04-06 | Platt; David | Composition and method for treating fungal disease in animals |
| US5965545A (en) * | 1996-10-15 | 1999-10-12 | State Of Israel, Ministry Of Agriculture, Agricultural Research Organization, The Volcani Center | Compositions and method for controlling fungal disease in plants |
| US5730876A (en) * | 1997-05-30 | 1998-03-24 | Hyang-Ja You | Separation and purification of low molecular weight chitosan using multi-step membrane separation process |
| US5997893A (en) * | 1998-01-20 | 1999-12-07 | Ethicon, Inc. | Alcohol based anti-microbial compositions with cosmetic appearance |
| US5972358A (en) * | 1998-01-20 | 1999-10-26 | Ethicon, Inc. | Low tack lotion, gels and creams |
| US6248343B1 (en) | 1998-01-20 | 2001-06-19 | Ethicon, Inc. | Therapeutic antimicrobial compositions |
| US6022551A (en) * | 1998-01-20 | 2000-02-08 | Ethicon, Inc. | Antimicrobial composition |
| CA2507017A1 (en) * | 2003-05-07 | 2005-01-20 | Research Institute For Production Development | Chitin oligomer composition and/or chitosan oligomer composition, and process for producing the same |
| US20050148546A1 (en) * | 2003-12-09 | 2005-07-07 | Grund Alan D. | Deacetylation of N-acetylglucosamine |
| KR100831335B1 (ko) * | 2006-06-22 | 2008-05-22 | 부경대학교 산학협력단 | 인간 피부 섬유아세포에서 메트릭스메탈로프로테이나제-2의 발현 및 활성을 억제시키는키토올리고사카라이드 화합물 및 이를 함유한 메트릭스메탈로프로테이나제-2 억제제 |
| EP3058826A1 (en) | 2011-09-08 | 2016-08-24 | Novozymes BioAG A/S | Seed treatment methods and compositions |
| RU2658362C1 (ru) | 2011-09-14 | 2018-06-21 | Новозимс Биоаг А/С | Применение липохитоолигосахаридов и/или хитоолигосахаридов в комбинации с микроорганизмами, придающими растворимость фосфатам, для усиления роста растений |
| BR112014006919B1 (pt) | 2011-09-23 | 2019-05-21 | Novozymes Bioag A/S | Método para intensificar o crescimento e/ou rendimento de plantas |
| CN104066328B (zh) | 2011-09-23 | 2016-03-23 | 诺维信生物农业公司 | 用于增强大豆生长的壳寡糖和方法 |
| RU2612428C2 (ru) | 2011-09-23 | 2017-03-09 | Новозимс Биоаг А/С | Комбинации липохитоолигосахаридов и способы их применения для усиления роста растений |
| US9055747B2 (en) | 2011-09-23 | 2015-06-16 | Novozymes Bioag A/S | Chitooligosaccharides and methods for use in enhancing corn growth |
| ES2936811T3 (es) | 2013-03-12 | 2023-03-22 | Wellstat Vaccines Llc | Conjugado para inducir anticuerpos dirigidos a polisacáridos de la pared celular fúngica |
| US9169376B2 (en) * | 2013-07-05 | 2015-10-27 | Boco Technology Inc. | Chitin nanowhisker composites and methods |
| ES2843877T3 (es) * | 2016-04-27 | 2021-07-20 | Showa Denko Kk | Métodos para producir oligómero de quitina, N-acetilglucosamina, y 1-O-alquil-N-acetilglucosamina |
| CN111239314B (zh) * | 2018-11-29 | 2021-09-28 | 中国科学院大连化学物理研究所 | 一种几丁寡糖的分离分析方法 |
| AU2020415493A1 (en) * | 2019-12-26 | 2022-08-18 | Centre For Cellular And Molecular Platforms | Therapeutic molecules for combating sepsis |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3989535A (en) * | 1974-02-11 | 1976-11-02 | American Cyanamid Company | Solution of poly(N-acetyl-D-glucosamine) |
| FR2357645A1 (fr) * | 1976-07-07 | 1978-02-03 | Agronomique Inst Nat Rech | Methode et systeme automatique de dosage d'amidon et corps similaires |
| IT1144697B (it) * | 1981-04-06 | 1986-10-29 | Texcontor Ets | Derivato semi-sintetico della chitina processo per la sua preparazione e composizioni terapeutiche che lo comprendono come principio attivo |
| US4424346A (en) * | 1981-06-04 | 1984-01-03 | Canadian Patents And Development Ltd. | Derivatives of chitins, chitosans and other polysaccharides |
| US4532321A (en) * | 1982-06-14 | 1985-07-30 | University Of Delaware | Microcrystalline chitin and method of manufacture |
| JPS61271296A (ja) * | 1985-05-28 | 1986-12-01 | Kyogyo Kumiai N F I | Ｎ−アセチルキトオリゴ糖の製造方法 |
-
1985
- 1985-12-11 JP JP60278688A patent/JPS62138496A/ja active Granted
-
1986
- 1986-12-09 CA CA000524841A patent/CA1297832C/en not_active Expired - Fee Related
- 1986-12-10 EP EP86309609A patent/EP0226452B1/en not_active Expired - Lifetime
- 1986-12-10 DK DK592886A patent/DK592886A/da not_active Application Discontinuation
- 1986-12-10 DE DE8686309609T patent/DE3687142T2/de not_active Expired - Fee Related
- 1986-12-10 FI FI865024A patent/FI80713C/fi not_active IP Right Cessation
- 1986-12-10 ES ES86309609T patent/ES2043604T3/es not_active Expired - Lifetime
- 1986-12-10 NO NO864982A patent/NO167747C/no not_active IP Right Cessation
- 1986-12-11 KR KR1019860010582A patent/KR900002853B1/ko not_active IP Right Cessation
- 1986-12-11 US US06/940,358 patent/US4804750A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62138496A (ja) | 1987-06-22 |
| FI865024A0 (fi) | 1986-12-10 |
| NO167747C (no) | 1991-12-04 |
| JPH0153877B2 (ko) | 1989-11-15 |
| DK592886D0 (da) | 1986-12-10 |
| ES2043604T3 (es) | 1994-01-01 |
| DE3687142T2 (de) | 1993-03-25 |
| DE3687142D1 (de) | 1992-12-24 |
| EP0226452A3 (en) | 1988-08-03 |
| DK592886A (da) | 1987-06-12 |
| EP0226452A2 (en) | 1987-06-24 |
| CA1297832C (en) | 1992-03-24 |
| NO864982D0 (no) | 1986-12-10 |
| FI865024A (fi) | 1987-06-12 |
| NO864982L (no) | 1987-06-12 |
| FI80713B (fi) | 1990-03-30 |
| NO167747B (no) | 1991-08-26 |
| EP0226452B1 (en) | 1992-11-19 |
| FI80713C (fi) | 1990-07-10 |
| KR900002853B1 (ko) | 1990-05-01 |
| US4804750A (en) | 1989-02-14 |
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