JP2003510330A5 - - Google Patents
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- JP2003510330A5 JP2003510330A5 JP2001526548A JP2001526548A JP2003510330A5 JP 2003510330 A5 JP2003510330 A5 JP 2003510330A5 JP 2001526548 A JP2001526548 A JP 2001526548A JP 2001526548 A JP2001526548 A JP 2001526548A JP 2003510330 A5 JP2003510330 A5 JP 2003510330A5
- Authority
- JP
- Japan
- Prior art keywords
- residue
- oligosaccharide
- group
- monosaccharide
- glc
- 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.)
- Pending
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- 150000002482 oligosaccharides Chemical class 0.000 description 31
- 150000002772 monosaccharides Chemical group 0.000 description 28
- 229920001542 oligosaccharide Polymers 0.000 description 26
- 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 description 14
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical group CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 125000003399 alpha-L-fucosyl group Chemical group 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 150000004676 glycans Chemical class 0.000 description 6
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 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 description 5
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 4
- 108010019236 Fucosyltransferases Proteins 0.000 description 4
- 102000006471 Fucosyltransferases Human genes 0.000 description 4
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 0 C**C(*)(*)OC(C(*)C1O)OC(CO)C1OC* Chemical compound C**C(*)(*)OC(C(*)C1O)OC(CO)C1OC* 0.000 description 3
- LQEBEXMHBLQMDB-UHFFFAOYSA-N GDP-L-fucose Natural products OC1C(O)C(O)C(C)OC1OP(O)(=O)OP(O)(=O)OCC1C(O)C(O)C(N2C3=C(C(N=C(N)N3)=O)N=C2)O1 LQEBEXMHBLQMDB-UHFFFAOYSA-N 0.000 description 3
- LQEBEXMHBLQMDB-JGQUBWHWSA-N GDP-beta-L-fucose Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=C(C(NC(N)=N3)=O)N=C2)O1 LQEBEXMHBLQMDB-JGQUBWHWSA-N 0.000 description 3
- OVRNDRQMDRJTHS-KEWYIRBNSA-N N-acetyl-D-galactosamine Chemical group CC(=O)N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-KEWYIRBNSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 108010083651 3-galactosyl-N-acetylglucosaminide 4-alpha-L-fucosyltransferase Proteins 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 2
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 2
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 description 2
- SHZGCJCMOBCMKK-PQMKYFCFSA-N L-Fucose Natural products C[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O SHZGCJCMOBCMKK-PQMKYFCFSA-N 0.000 description 2
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 2
- MBLBDJOUHNCFQT-UHFFFAOYSA-N N-acetyl-D-galactosamine Natural products CC(=O)NC(C=O)C(O)C(O)C(O)CO MBLBDJOUHNCFQT-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002773 nucleotide Substances 0.000 description 2
- 125000003729 nucleotide group Chemical group 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 101710185215 4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT5 Proteins 0.000 description 1
- 102100035274 4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT5 Human genes 0.000 description 1
- PSGQCCSGKGJLRL-UHFFFAOYSA-N 4-methyl-2h-chromen-2-one Chemical group C1=CC=CC2=C1OC(=O)C=C2C PSGQCCSGKGJLRL-UHFFFAOYSA-N 0.000 description 1
- PZUPAGRIHCRVKN-UHFFFAOYSA-N 5-[5-[3,4-dihydroxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxymethyl]-5-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound OCC1OC(O)C(O)C(O)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(COC4C(C(O)C(O)CO4)O)O3)O)C(COC3C(C(O)C(O)CO3)O)O2)O)C(COC2C(C(O)C(O)CO2)O)O1 PZUPAGRIHCRVKN-UHFFFAOYSA-N 0.000 description 1
- 125000003535 D-glucopyranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H] 0.000 description 1
- 101001022183 Homo sapiens 4-galactosyl-N-acetylglucosaminide 3-alpha-L-fucosyltransferase FUT5 Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- OVRNDRQMDRJTHS-CBQIKETKSA-N N-Acetyl-D-Galactosamine Chemical compound CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-CBQIKETKSA-N 0.000 description 1
- BZBKTWJIYTYFBH-YSJWDAEMSA-N N-I,N-II,N-III,N-IV,N-V-Pentaacetylchito-pentaose Chemical group 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]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 BZBKTWJIYTYFBH-YSJWDAEMSA-N 0.000 description 1
- 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 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 102000007478 beta-N-Acetylhexosaminidases Human genes 0.000 description 1
- 108010085377 beta-N-Acetylhexosaminidases Proteins 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000002446 fucosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)[C@@H](O1)C)* 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 238000010829 isocratic elution Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI19992070 | 1999-09-28 | ||
| FI19992070A FI19992070A7 (fi) | 1999-09-28 | 1999-09-28 | Uudet fukosyloidut oligosakkaridit ja menetelmä niiden valmistamiseksi |
| PCT/FI2000/000803 WO2001023398A1 (en) | 1999-09-28 | 2000-09-21 | Novel fucosylated oligosaccharides and process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003510330A JP2003510330A (ja) | 2003-03-18 |
| JP2003510330A5 true JP2003510330A5 (enExample) | 2008-04-03 |
Family
ID=8555359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001526548A Pending JP2003510330A (ja) | 1999-09-28 | 2000-09-21 | 新規フコシル化オリゴ糖およびその製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6878819B1 (enExample) |
| EP (1) | EP1228079B1 (enExample) |
| JP (1) | JP2003510330A (enExample) |
| AT (1) | ATE273987T1 (enExample) |
| AU (1) | AU780370B2 (enExample) |
| CA (1) | CA2385295A1 (enExample) |
| DE (1) | DE60013161T2 (enExample) |
| FI (1) | FI19992070A7 (enExample) |
| NZ (1) | NZ518267A (enExample) |
| WO (1) | WO2001023398A1 (enExample) |
| ZA (1) | ZA200202184B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9904581D0 (sv) * | 1999-12-15 | 1999-12-15 | A & Science Invest Ab | A novel helicobacter pylori-binding substance and use thereof |
| FR2806077B1 (fr) * | 2000-03-07 | 2004-01-30 | Solvay | Procede pour l'obtention d'un hydrofluoroalcane epure, hydrofluoroalcane epure, utilisation de l'hydrofluoroalcane et methode d'analyse d'un hydrofluoroalcane |
| DE10145193C1 (de) | 2001-09-13 | 2003-03-13 | Sachtler Gmbh & Co Kg | Körpermontierbares Kameratragesystem mit einem multifunktionalen Verbund elektrischer Komponenten |
| WO2004065400A1 (en) * | 2003-01-20 | 2004-08-05 | Glykos Finland Oy | Novel binding epitopes for helicobacter pylori and use thereof |
| JP5331293B2 (ja) * | 2006-04-28 | 2013-10-30 | 公益財団法人野口研究所 | 多様性を表現するオリゴ糖またはその誘導体 |
| EP2153455B1 (en) * | 2007-06-01 | 2020-04-29 | PerkinElmer Health Sciences, Inc. | Atmospheric pressure ion source performance enhancement |
| US7919746B2 (en) * | 2007-10-16 | 2011-04-05 | Perkinelmer Health Sciences, Inc. | Atmospheric pressure ion source performance enhancement |
| JP5605541B2 (ja) * | 2009-03-06 | 2014-10-15 | 国立大学法人埼玉大学 | フコシルキトビオース誘導体の製造方法 |
| PL2944690T3 (pl) * | 2010-10-11 | 2018-05-30 | Jennewein Biotechnologie Gmbh | Nowe fukozylotransferazy i ich zastosowanie |
| DK2479263T3 (da) * | 2011-01-20 | 2014-02-03 | Jennewein Biotechnologie Gmbh | Nye fucosyltransferaser og deres anvendelser |
| EP2690959B1 (en) | 2011-03-31 | 2016-03-23 | Novozymes Biologicals, Inc. | Competitive and effective bradyrhizobium japonicum strains |
| PL2747565T3 (pl) | 2011-09-08 | 2017-09-29 | Novozymes Bioag A/S | Sposoby zaprawiania nasion |
| CA2848856C (en) | 2011-09-14 | 2020-04-28 | Novozymes Bioag A/S | Use of lipochito-oligosaccharides and/or chito-oligosaccharides in combination with phosphate-solubilizing microorganisms to enhance plant growth |
| US9554575B2 (en) | 2011-09-23 | 2017-01-31 | Novozymes Bioag A/S | Combinations of lipo-chitooligosaccharides and methods for use in enhancing plant growth |
| WO2013044212A1 (en) | 2011-09-23 | 2013-03-28 | Novozymes Biologicals Holdings A/S | Chitooligosaccharides and methods for use in enhancing soybean growth |
| US9055746B2 (en) | 2011-09-23 | 2015-06-16 | Novozymes Bioag A/S | Chitooligosaccharides and methods for use in enhancing plant growth |
| IN2014CN02911A (enExample) | 2011-09-23 | 2015-07-03 | Novozymes Bioag As | |
| CA2859425C (en) | 2011-12-16 | 2020-05-12 | Novozymes Bioag A/S | Bradyrhizobium strains |
| CN103484526A (zh) * | 2012-06-14 | 2014-01-01 | 北京和信非凡生物技术有限公司 | 一种β-氨基己糖苷酶A酶活性检测方法、底物和试剂 |
| CN103424500A (zh) * | 2013-08-16 | 2013-12-04 | 浙江树人大学 | 离子色谱定性检测壳寡糖的方法及应用 |
| AU2016383059B2 (en) | 2015-12-28 | 2022-10-27 | Monsanto Technology Llc | Stable inoculant compositions and methods for producing same |
| KR20190076046A (ko) * | 2016-11-10 | 2019-07-01 | 산도즈 아게 | 단백질 용액의 탈염 공정 |
| CN115058465B (zh) * | 2022-06-30 | 2025-03-07 | 山东大学 | 一种岩藻糖基化软骨素及其制备方法和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3476455B2 (ja) | 1991-03-18 | 2003-12-10 | ザ スクリップス リサーチ インスティテュート | ＮｅｕＡｃα２、６Ｇａｌβ１、４ＧｌｃＮＡｃ及びシアリルＬｅｘの合成法 |
| US5374655A (en) * | 1991-06-10 | 1994-12-20 | Alberta Research Council | Methods for the synthesis of monofucosylated oligosaccharides terminating in di-N-acetyllactosaminyl structures |
| US6319695B1 (en) * | 1991-10-15 | 2001-11-20 | The Scripps Research Insitute | Production of fucosylated carbohydrates by enzymatic fucosylation synthesis of sugar nucleotides; and in situ regeneration of GDP-fucose |
| US5922577A (en) * | 1995-04-11 | 1999-07-13 | Cytel Corporation | Enzymatic synthesis of glycosidic linkages |
| ATE196928T1 (de) * | 1995-07-13 | 2000-10-15 | Bioflexin Ab | Verfahren zur herstellung von derivaten von glc- beta 1-4-glc-n-acetyl |
| US5972907A (en) | 1997-10-31 | 1999-10-26 | Health Research, Inc. | Synthetic core 2-like branched structures containing GalNAc-lewisx and Neu5Acα2-3Galβ1-3GalNAc sequences as novel ligands for selectins |
-
1999
- 1999-09-28 FI FI19992070A patent/FI19992070A7/fi unknown
-
2000
- 2000-09-21 AU AU72930/00A patent/AU780370B2/en not_active Ceased
- 2000-09-21 DE DE60013161T patent/DE60013161T2/de not_active Expired - Lifetime
- 2000-09-21 JP JP2001526548A patent/JP2003510330A/ja active Pending
- 2000-09-21 WO PCT/FI2000/000803 patent/WO2001023398A1/en not_active Ceased
- 2000-09-21 US US10/089,229 patent/US6878819B1/en not_active Expired - Fee Related
- 2000-09-21 NZ NZ518267A patent/NZ518267A/en not_active IP Right Cessation
- 2000-09-21 CA CA002385295A patent/CA2385295A1/en not_active Abandoned
- 2000-09-21 AT AT00960731T patent/ATE273987T1/de not_active IP Right Cessation
- 2000-09-21 EP EP00960731A patent/EP1228079B1/en not_active Expired - Lifetime
-
2002
- 2002-03-18 ZA ZA200202184A patent/ZA200202184B/xx unknown
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