JP2012031107A - ヘテロ二糖、キトビオース、及びジ‐n‐アセチルキトビオースの製造方法、並びにそれらの用途 - Google Patents
ヘテロ二糖、キトビオース、及びジ‐n‐アセチルキトビオースの製造方法、並びにそれらの用途 Download PDFInfo
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- JP2012031107A JP2012031107A JP2010172466A JP2010172466A JP2012031107A JP 2012031107 A JP2012031107 A JP 2012031107A JP 2010172466 A JP2010172466 A JP 2010172466A JP 2010172466 A JP2010172466 A JP 2010172466A JP 2012031107 A JP2012031107 A JP 2012031107A
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- heterodisaccharide
- chitin
- producing
- glucosamine
- chitobiose
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- QLTSDROPCWIKKY-PMCTYKHCSA-N beta-D-glucosaminyl-(1->4)-beta-D-glucosamine Chemical compound O[C@@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](N)[C@@H](O)[C@H](O)[C@@H](CO)O1 QLTSDROPCWIKKY-PMCTYKHCSA-N 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 74
- -1 hetero disaccharide Chemical class 0.000 title abstract description 21
- 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 title abstract description 17
- 229920002101 Chitin Polymers 0.000 claims abstract description 82
- 238000003381 deacetylation reaction Methods 0.000 claims abstract description 53
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical group N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 claims abstract description 51
- 230000006196 deacetylation Effects 0.000 claims abstract description 39
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical group 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 abstract description 38
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 38
- 230000007062 hydrolysis Effects 0.000 claims abstract description 33
- 239000002253 acid Substances 0.000 claims abstract description 10
- 239000000243 solution Substances 0.000 claims description 37
- 238000000354 decomposition reaction Methods 0.000 claims description 25
- 239000003729 cation exchange resin Substances 0.000 claims description 14
- 235000013305 food Nutrition 0.000 claims description 14
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000007857 degradation product Substances 0.000 claims description 8
- 239000012528 membrane Substances 0.000 claims description 8
- 235000013361 beverage Nutrition 0.000 claims description 6
- 230000000850 deacetylating effect Effects 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 6
- 239000003957 anion exchange resin Substances 0.000 claims description 5
- 238000001223 reverse osmosis Methods 0.000 claims description 4
- 239000003929 acidic solution Substances 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 21
- 229940088623 biologically active substance Drugs 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 27
- 229920001542 oligosaccharide Polymers 0.000 description 26
- 150000002482 oligosaccharides Chemical class 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000463 material Substances 0.000 description 20
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 18
- 229950006780 n-acetylglucosamine Drugs 0.000 description 18
- 230000035484 reaction time Effects 0.000 description 18
- 239000003513 alkali Substances 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000006386 neutralization reaction Methods 0.000 description 11
- 239000002537 cosmetic Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 150000002016 disaccharides Chemical class 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000011033 desalting Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- 229930182470 glycoside Natural products 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 210000000813 small intestine Anatomy 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000019640 taste Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000003796 beauty Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000000909 electrodialysis Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002772 monosaccharides Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- 102000012286 Chitinases Human genes 0.000 description 1
- 108010022172 Chitinases Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- FZHXIRIBWMQPQF-UHFFFAOYSA-N Glc-NH2 Natural products O=CC(N)C(O)C(O)C(O)CO FZHXIRIBWMQPQF-UHFFFAOYSA-N 0.000 description 1
- 102000002268 Hexosaminidases Human genes 0.000 description 1
- 108010000540 Hexosaminidases Proteins 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 description 1
- 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 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 235000019606 astringent taste Nutrition 0.000 description 1
- TVLSMEPJGATPGK-CGKOVJDHSA-N beta-D-glucosaminyl-(1->4)-N-acetyl-beta-D-glucosamine Chemical compound O[C@@H]1[C@@H](NC(=O)C)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](N)[C@@H](O)[C@H](O)[C@@H](CO)O1 TVLSMEPJGATPGK-CGKOVJDHSA-N 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000000833 heterodimer Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 239000012266 salt solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 150000004044 tetrasaccharides Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
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- Coloring Foods And Improving Nutritive Qualities (AREA)
- Non-Alcoholic Beverages (AREA)
- Saccharide Compounds (AREA)
Abstract
【解決手段】本発明のヘテロ二糖の製造方法は、非還元末端側がD‐グルコサミン残基であって還元末端側がN‐アセチル‐D‐グルコサミン残基であるヘテロ二糖の製造方法であって、キチンを部分的に脱アセチル化する脱アセチル化工程と、部分的に脱アセチル化された前記キチンを酸で加水分解するキチン加水分解工程と、を有している。
【選択図】図1
Description
Claims (9)
- 非還元末端側がD‐グルコサミン残基であって還元末端側がN‐アセチル‐D‐グルコサミン残基であるヘテロ二糖の製造方法であって、
キチンを部分的に脱アセチル化する脱アセチル化工程と、
部分的に脱アセチル化された前記キチンを酸で加水分解するキチン加水分解工程と、を有することを特徴とするヘテロ二糖の製造方法。 - 前記キチン加水分解工程を経た分解溶液中に含まれる前記ヘテロ二糖を、陽イオン交換樹脂に吸着させ、その後酸性液で溶出することにより、前記ヘテロ二糖を精製することを特徴とする請求項1に記載のヘテロ二糖の製造方法。
- 前記酸性液で溶出された溶出液を陰イオン交換樹脂を用いて酸性を中和させて前記ヘテロ二糖を精製することを特徴とする請求項2に記載のヘテロ二糖の製造方法。
- 前記キチン加水分解工程を経た分解溶液中に含まれる前記ヘテロ二糖を、逆浸透膜を用いて精製することを特徴とする請求項1に記載のヘテロ二糖の製造方法。
- 請求項1乃至4のいずれかに記載のヘテロ二糖の製造方法により製造された前記ヘテロ二糖の前記D‐グルコサミン残基をN‐アセチル化することを特徴とするジ‐N‐アセチルキトビオースの製造方法。
- 請求項1乃至4のいずれかに記載のヘテロ二糖の製造方法により製造された前記ヘテロ二糖の前記N‐アセチル‐D‐グルコサミン残基を脱アセチル化することを特徴とするキトビオースの製造方法。
- 請求項1乃至4に記載のヘテロ二糖の製造方法により製造された前記ヘテロ二糖、又は請求項6に記載のキトビオースの製造方法により製造された前記キトビオースを含有することを特徴とする食品。
- 請求項1乃至4に記載のヘテロ二糖の製造方法により製造された前記ヘテロ二糖、又は請求項6に記載のキトビオースの製造方法により製造された前記キトビオースを含有することを特徴とする飲料。
- 請求項1記載のヘテロ二糖を含有することを特徴とするキチン分解物。
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JP2010172466A JP2012031107A (ja) | 2010-07-30 | 2010-07-30 | ヘテロ二糖、キトビオース、及びジ‐n‐アセチルキトビオースの製造方法、並びにそれらの用途 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015098634A1 (ja) * | 2013-12-25 | 2015-07-02 | 株式会社海月研究所 | 水不溶性高分子化合物の分解物の連続的製造方法 |
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JPS5347479A (en) * | 1976-10-12 | 1978-04-27 | Ajinomoto Co Inc | Water-soluble, partially deacetylated chitin and its preparation |
JPH057496A (ja) * | 1991-07-02 | 1993-01-19 | Shin Etsu Chem Co Ltd | オリゴ糖の製造方法 |
JPH05320204A (ja) * | 1992-05-27 | 1993-12-03 | Katakura Chitsukarin Kk | N−アセチルキトオリゴ糖の製造法 |
JP2002165578A (ja) * | 2000-11-29 | 2002-06-11 | Yaizu Suisankagaku Industry Co Ltd | 免疫力強化組成物 |
JP2003212889A (ja) * | 2002-01-21 | 2003-07-30 | Yaizu Suisankagaku Industry Co Ltd | キトサンオリゴ糖の製造方法及びキトサンオリゴ糖アルコール体の製造方法 |
JP2004210667A (ja) * | 2002-12-27 | 2004-07-29 | Yaizu Suisankagaku Industry Co Ltd | 新規モノアセチルキトオリゴ糖及びその製造方法、並びにキチンオリゴ糖及びキトサンオリゴ糖の製造方法 |
JP2006517408A (ja) * | 2003-02-06 | 2006-07-27 | アドバンスド バイオポリマーズ エーエス | キトサン食物 |
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2010
- 2010-07-30 JP JP2010172466A patent/JP2012031107A/ja active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS5347479A (en) * | 1976-10-12 | 1978-04-27 | Ajinomoto Co Inc | Water-soluble, partially deacetylated chitin and its preparation |
JPH057496A (ja) * | 1991-07-02 | 1993-01-19 | Shin Etsu Chem Co Ltd | オリゴ糖の製造方法 |
JPH05320204A (ja) * | 1992-05-27 | 1993-12-03 | Katakura Chitsukarin Kk | N−アセチルキトオリゴ糖の製造法 |
JP2002165578A (ja) * | 2000-11-29 | 2002-06-11 | Yaizu Suisankagaku Industry Co Ltd | 免疫力強化組成物 |
JP2003212889A (ja) * | 2002-01-21 | 2003-07-30 | Yaizu Suisankagaku Industry Co Ltd | キトサンオリゴ糖の製造方法及びキトサンオリゴ糖アルコール体の製造方法 |
JP2004210667A (ja) * | 2002-12-27 | 2004-07-29 | Yaizu Suisankagaku Industry Co Ltd | 新規モノアセチルキトオリゴ糖及びその製造方法、並びにキチンオリゴ糖及びキトサンオリゴ糖の製造方法 |
JP2006517408A (ja) * | 2003-02-06 | 2006-07-27 | アドバンスド バイオポリマーズ エーエス | キトサン食物 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2015098634A1 (ja) * | 2013-12-25 | 2015-07-02 | 株式会社海月研究所 | 水不溶性高分子化合物の分解物の連続的製造方法 |
CN106061991A (zh) * | 2013-12-25 | 2016-10-26 | 株式会社海月研究所 | 水不溶性高分子化合物的分解物的连续制造方法 |
US10239915B2 (en) | 2013-12-25 | 2019-03-26 | Jellyfish Research Laboratories, Inc. | Method for continuous production of degradation product of water-insoluble polymeric compound |
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