JP4166846B2 - ヘパリン結合担体及びフルクトース−1,6−ビスリン酸アルドラーゼの分離方法 - Google Patents
ヘパリン結合担体及びフルクトース−1,6−ビスリン酸アルドラーゼの分離方法 Download PDFInfo
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- JP4166846B2 JP4166846B2 JP21271497A JP21271497A JP4166846B2 JP 4166846 B2 JP4166846 B2 JP 4166846B2 JP 21271497 A JP21271497 A JP 21271497A JP 21271497 A JP21271497 A JP 21271497A JP 4166846 B2 JP4166846 B2 JP 4166846B2
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- Prior art keywords
- heparin
- δdihs
- fructose
- carrier
- bisphosphate aldolase
- Prior art date
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- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 title claims description 138
- 229920000669 heparin Polymers 0.000 title claims description 106
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- 238000000034 method Methods 0.000 title claims description 55
- 102000001390 Fructose-Bisphosphate Aldolase Human genes 0.000 title claims description 34
- 108010068561 Fructose-Bisphosphate Aldolase Proteins 0.000 title claims description 34
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- 108090000790 Enzymes Proteins 0.000 claims description 35
- 150000002016 disaccharides Chemical class 0.000 claims description 22
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- 238000004458 analytical method Methods 0.000 claims description 14
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- 239000000203 mixture Substances 0.000 claims description 10
- 210000001519 tissue Anatomy 0.000 claims description 9
- 229920002683 Glycosaminoglycan Polymers 0.000 claims description 6
- 210000004556 brain Anatomy 0.000 claims description 5
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- 229920002567 Chondroitin Polymers 0.000 claims description 4
- DLGJWSVWTWEWBJ-HGGSSLSASA-N chondroitin Chemical compound CC(O)=N[C@@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1OC1[C@H](O)[C@H](O)C=C(C(O)=O)O1 DLGJWSVWTWEWBJ-HGGSSLSASA-N 0.000 claims description 4
- 230000015556 catabolic process Effects 0.000 claims description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- 239000012153 distilled water Substances 0.000 description 18
- MSWZFWKMSRAUBD-IVMDWMLBSA-N glucosamine group Chemical group OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 125000003277 amino group Chemical group 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000872 buffer Substances 0.000 description 13
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- 239000011541 reaction mixture Substances 0.000 description 13
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 12
- 229920000936 Agarose Polymers 0.000 description 11
- -1 aminohexyl Chemical group 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 8
- 229960002442 glucosamine Drugs 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- 108090000935 Antithrombin III Proteins 0.000 description 3
- XPYBSIWDXQFNMH-UHFFFAOYSA-N D-fructose 1,6-bisphosphate Natural products OP(=O)(O)OCC(O)C(O)C(O)C(=O)COP(O)(O)=O XPYBSIWDXQFNMH-UHFFFAOYSA-N 0.000 description 3
- 102000001708 Protein Isoforms Human genes 0.000 description 3
- 108010029485 Protein Isoforms Proteins 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000003172 aldehyde group Chemical group 0.000 description 3
- RNBGYGVWRKECFJ-ZXXMMSQZSA-N alpha-D-fructofuranose 1,6-bisphosphate Chemical compound O[C@H]1[C@H](O)[C@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O RNBGYGVWRKECFJ-ZXXMMSQZSA-N 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 238000003745 diagnosis Methods 0.000 description 3
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- 238000000502 dialysis Methods 0.000 description 3
- 230000029087 digestion Effects 0.000 description 3
- RNBGYGVWRKECFJ-UHFFFAOYSA-N fructose-1,6-phosphate Natural products OC1C(O)C(O)(COP(O)(O)=O)OC1COP(O)(O)=O RNBGYGVWRKECFJ-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000002628 heparin derivative Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- ZKLLSNQJRLJIGT-UYFOZJQFSA-N keto-D-fructose 1-phosphate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)COP(O)(O)=O ZKLLSNQJRLJIGT-UYFOZJQFSA-N 0.000 description 3
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 3
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 3
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- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229920003169 water-soluble polymer Polymers 0.000 description 3
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 102100022977 Antithrombin-III Human genes 0.000 description 2
- 102000000587 Glycerolphosphate Dehydrogenase Human genes 0.000 description 2
- 108010041921 Glycerolphosphate Dehydrogenase Proteins 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- 102000005924 Triose-Phosphate Isomerase Human genes 0.000 description 2
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- 230000002490 cerebral effect Effects 0.000 description 2
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- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
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- 239000007999 glycylglycine buffer Substances 0.000 description 2
- 108010083213 heparitinsulfate lyase Proteins 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
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- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
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- PKFWAYWIOOSXIO-UHFFFAOYSA-N n,n-dibutylbutan-1-amine;ethanol Chemical compound CCO.CCCCN(CCCC)CCCC PKFWAYWIOOSXIO-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000001180 sulfating effect Effects 0.000 description 2
- 230000019635 sulfation Effects 0.000 description 2
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 1
- 102000004411 Antithrombin III Human genes 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
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- 230000004913 activation Effects 0.000 description 1
- 231100000354 acute hepatitis Toxicity 0.000 description 1
- 206010000891 acute myocardial infarction Diseases 0.000 description 1
- 238000012870 ammonium sulfate precipitation Methods 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 229960005348 antithrombin iii Drugs 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
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- 238000006477 desulfuration reaction Methods 0.000 description 1
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- 150000004676 glycans Chemical class 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
- SMBBZHGTZJNSRQ-UHFFFAOYSA-N n'-(6,6-dichlorohexyl)methanediimine Chemical compound ClC(Cl)CCCCCN=C=N SMBBZHGTZJNSRQ-UHFFFAOYSA-N 0.000 description 1
- 238000001426 native polyacrylamide gel electrophoresis Methods 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
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Images
Landscapes
- Enzymes And Modification Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21271497A JP4166846B2 (ja) | 1997-07-24 | 1997-07-24 | ヘパリン結合担体及びフルクトース−1,6−ビスリン酸アルドラーゼの分離方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21271497A JP4166846B2 (ja) | 1997-07-24 | 1997-07-24 | ヘパリン結合担体及びフルクトース−1,6−ビスリン酸アルドラーゼの分離方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH1135603A JPH1135603A (ja) | 1999-02-09 |
| JPH1135603A5 JPH1135603A5 (enExample) | 2005-05-26 |
| JP4166846B2 true JP4166846B2 (ja) | 2008-10-15 |
Family
ID=16627219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21271497A Expired - Fee Related JP4166846B2 (ja) | 1997-07-24 | 1997-07-24 | ヘパリン結合担体及びフルクトース−1,6−ビスリン酸アルドラーゼの分離方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4166846B2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4633223B2 (ja) * | 1999-03-31 | 2011-02-16 | 生化学工業株式会社 | 血管内皮細胞増殖因子依存性血管内皮細胞増殖の抑制剤 |
| JP4633233B2 (ja) * | 2000-06-29 | 2011-02-16 | 生化学工業株式会社 | クラミジア感染症処置剤 |
| US7687609B2 (en) * | 2006-05-19 | 2010-03-30 | National Institute Of Advanced Industrial Science And Technology | Galectin-glycosaminoglycan complex and method for controlling galectin activity |
| CN103157452B (zh) * | 2013-03-30 | 2014-12-31 | 福州大学 | 脱硫酸化肝素衍生物亲和色谱材料的制备方法 |
-
1997
- 1997-07-24 JP JP21271497A patent/JP4166846B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH1135603A (ja) | 1999-02-09 |
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