JP2002045196A - 混成型糖鎖の酵素的合成方法 - Google Patents
混成型糖鎖の酵素的合成方法Info
- Publication number
- JP2002045196A JP2002045196A JP2000234814A JP2000234814A JP2002045196A JP 2002045196 A JP2002045196 A JP 2002045196A JP 2000234814 A JP2000234814 A JP 2000234814A JP 2000234814 A JP2000234814 A JP 2000234814A JP 2002045196 A JP2002045196 A JP 2002045196A
- Authority
- JP
- Japan
- Prior art keywords
- sugar chain
- acetylglucosamine
- formula
- residue
- saccharide
- 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- Withdrawn
Links
- 235000000346 sugar Nutrition 0.000 title claims abstract description 109
- 238000000034 method Methods 0.000 title claims description 15
- 230000002255 enzymatic effect Effects 0.000 title abstract description 3
- 238000003786 synthesis reaction Methods 0.000 title description 8
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 150000001720 carbohydrates Chemical class 0.000 claims abstract description 36
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims abstract description 22
- 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 abstract description 22
- 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 abstract description 20
- 239000000758 substrate Substances 0.000 claims abstract description 20
- 229950006780 n-acetylglucosamine Drugs 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 10
- 102000004357 Transferases Human genes 0.000 claims abstract description 10
- 108090000992 Transferases Proteins 0.000 claims abstract description 10
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract description 10
- 239000008103 glucose Substances 0.000 claims abstract description 10
- 229930182830 galactose Natural products 0.000 claims abstract description 5
- 239000000872 buffer Substances 0.000 claims description 15
- 235000014633 carbohydrates Nutrition 0.000 claims description 13
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 9
- -1 2-aminopyridyl group Chemical group 0.000 claims description 8
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Chemical group OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims description 7
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical group OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 7
- 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 claims description 7
- 229960001230 asparagine Drugs 0.000 claims description 7
- 235000009582 asparagine Nutrition 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 150000002696 manganese Chemical class 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 7
- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 6
- 229920001184 polypeptide Polymers 0.000 claims description 6
- LFTYTUAZOPRMMI-CFRASDGPSA-N UDP-N-acetyl-alpha-D-glucosamine Chemical compound O1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](NC(=O)C)[C@H]1OP(O)(=O)OP(O)(=O)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(NC(=O)C=C2)=O)O1 LFTYTUAZOPRMMI-CFRASDGPSA-N 0.000 claims description 5
- HSCJRCZFDFQWRP-ABVWGUQPSA-N UDP-alpha-D-galactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(NC(=O)C=C2)=O)O1 HSCJRCZFDFQWRP-ABVWGUQPSA-N 0.000 claims description 5
- LFTYTUAZOPRMMI-UHFFFAOYSA-N UNPD164450 Natural products O1C(CO)C(O)C(O)C(NC(=O)C)C1OP(O)(=O)OP(O)(=O)OCC1C(O)C(O)C(N2C(NC(=O)C=C2)=O)O1 LFTYTUAZOPRMMI-UHFFFAOYSA-N 0.000 claims description 5
- HSCJRCZFDFQWRP-UHFFFAOYSA-N Uridindiphosphoglukose Natural products OC1C(O)C(O)C(CO)OC1OP(O)(=O)OP(O)(=O)OCC1C(O)C(O)C(N2C(NC(=O)C=C2)=O)O1 HSCJRCZFDFQWRP-UHFFFAOYSA-N 0.000 claims description 5
- 102000030902 Galactosyltransferase Human genes 0.000 claims description 3
- 108060003306 Galactosyltransferase Proteins 0.000 claims description 3
- 229910021380 Manganese Chloride Inorganic materials 0.000 claims description 3
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical group Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 claims description 3
- 229940099607 manganese chloride Drugs 0.000 claims description 3
- 235000002867 manganese chloride Nutrition 0.000 claims description 3
- 239000011565 manganese chloride Substances 0.000 claims description 3
- DUKURNFHYQXCJG-UHFFFAOYSA-N Lewis A pentasaccharide Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(C)=O)C(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)OC1CO DUKURNFHYQXCJG-UHFFFAOYSA-N 0.000 claims 2
- 238000001308 synthesis method Methods 0.000 abstract 1
- 101000972916 Homo sapiens Alpha-1,3-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase Proteins 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 30
- 102100022622 Alpha-1,3-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase Human genes 0.000 description 29
- 238000004128 high performance liquid chromatography Methods 0.000 description 23
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- 108090000790 Enzymes Proteins 0.000 description 11
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 108010066476 ribonuclease B Proteins 0.000 description 9
- 241000588724 Escherichia coli Species 0.000 description 8
- 102000051366 Glycosyltransferases Human genes 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 4
- 229920000856 Amylose Polymers 0.000 description 4
- 102000003886 Glycoproteins Human genes 0.000 description 4
- 108090000288 Glycoproteins Proteins 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 101000588395 Bacillus subtilis (strain 168) Beta-hexosaminidase Proteins 0.000 description 3
- 101710175625 Maltose/maltodextrin-binding periplasmic protein Proteins 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- 241000193155 Clostridium botulinum Species 0.000 description 2
- 208000035220 Dyserythropoietic Congenital Anemia Diseases 0.000 description 2
- 102000002464 Galactosidases Human genes 0.000 description 2
- 108010093031 Galactosidases Proteins 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- FYGDTMLNYKFZSV-DZOUCCHMSA-N alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-D-Glcp Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-DZOUCCHMSA-N 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
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- 108020001507 fusion proteins Proteins 0.000 description 2
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- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 102000045442 glycosyltransferase activity proteins Human genes 0.000 description 2
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- 210000004185 liver Anatomy 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
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- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- UQBIAGWOJDEOMN-UHFFFAOYSA-N 2-O-(2-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranosyl)-D-mannopyranose Natural products OC1C(O)C(CO)OC(O)C1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(O)C(O)C(CO)O1 UQBIAGWOJDEOMN-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- 102100035248 Alpha-(1,3)-fucosyltransferase 4 Human genes 0.000 description 1
- 108030001720 Bontoxilysin Proteins 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 241000193403 Clostridium Species 0.000 description 1
- 241000672609 Escherichia coli BL21 Species 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 101001022185 Homo sapiens Alpha-(1,3)-fucosyltransferase 4 Proteins 0.000 description 1
- 101150017040 I gene Proteins 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- 239000007987 MES buffer Substances 0.000 description 1
- 102000012750 Membrane Glycoproteins Human genes 0.000 description 1
- 108010090054 Membrane Glycoproteins Proteins 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 102000016611 Proteoglycans Human genes 0.000 description 1
- 108010067787 Proteoglycans Proteins 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
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- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical group OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 229940053031 botulinum toxin Drugs 0.000 description 1
- 108700017751 botulinum toxin type C Proteins 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
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- 235000021277 colostrum Nutrition 0.000 description 1
- 235000021310 complex sugar Nutrition 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
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- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical group CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000234814A JP2002045196A (ja) | 2000-08-02 | 2000-08-02 | 混成型糖鎖の酵素的合成方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000234814A JP2002045196A (ja) | 2000-08-02 | 2000-08-02 | 混成型糖鎖の酵素的合成方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002045196A true JP2002045196A (ja) | 2002-02-12 |
| JP2002045196A5 JP2002045196A5 (https=) | 2007-06-28 |
Family
ID=18727132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000234814A Withdrawn JP2002045196A (ja) | 2000-08-02 | 2000-08-02 | 混成型糖鎖の酵素的合成方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2002045196A (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004058984A1 (ja) * | 2002-12-24 | 2004-07-15 | Otsuka Chemical Co., Ltd. | 糖鎖アスパラギン誘導体、糖鎖アスパラギンおよび糖鎖ならびにそれらの製造法 |
| CN100413889C (zh) * | 2002-12-24 | 2008-08-27 | 大塚化学株式会社 | 糖链天冬酰胺衍生物、糖链天冬酰胺和糖链以及它们的制造方法 |
-
2000
- 2000-08-02 JP JP2000234814A patent/JP2002045196A/ja not_active Withdrawn
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004058984A1 (ja) * | 2002-12-24 | 2004-07-15 | Otsuka Chemical Co., Ltd. | 糖鎖アスパラギン誘導体、糖鎖アスパラギンおよび糖鎖ならびにそれらの製造法 |
| AU2003296067B8 (en) * | 2002-12-24 | 2004-07-22 | Glytech, Inc. | Sugar chain asparagine derivatives, sugar chain asparagine, sugar chain, and processes for producing these |
| KR100736510B1 (ko) * | 2002-12-24 | 2007-07-06 | 오츠카 가가쿠 가부시키가이샤 | 당사슬 아스파라긴 유도체, 당사슬 아스파라긴, 당사슬 및그들의 제조법 |
| AU2003296067B2 (en) * | 2002-12-24 | 2007-08-23 | Glytech, Inc. | Sugar chain asparagine derivatives, sugar chain asparagine, sugar chain, and processes for producing these |
| US7304148B2 (en) | 2002-12-24 | 2007-12-04 | Otsuka Chemical Co., Ltd. | Sugar chain asparagine derivatives, sugar chain asparagine, sugar chain, and processes for producing these |
| CN100413889C (zh) * | 2002-12-24 | 2008-08-27 | 大塚化学株式会社 | 糖链天冬酰胺衍生物、糖链天冬酰胺和糖链以及它们的制造方法 |
| US8158763B2 (en) | 2002-12-24 | 2012-04-17 | Yasuhiro Kajihara | Sugar chain asparagine derivatives, sugar chain asparagine, sugar chain and processes for producing these |
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Effective date: 20070514 Free format text: JAPANESE INTERMEDIATE CODE: A523 |
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