CA2385295A1 - Novel fucosylated oligosaccharides and process for their preparation - Google Patents

Novel fucosylated oligosaccharides and process for their preparation Download PDF

Info

Publication number
CA2385295A1
CA2385295A1 CA002385295A CA2385295A CA2385295A1 CA 2385295 A1 CA2385295 A1 CA 2385295A1 CA 002385295 A CA002385295 A CA 002385295A CA 2385295 A CA2385295 A CA 2385295A CA 2385295 A1 CA2385295 A1 CA 2385295A1
Authority
CA
Canada
Prior art keywords
beta
glc
monosaccharide
glcnac
alpha
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.)
Abandoned
Application number
CA002385295A
Other languages
English (en)
French (fr)
Inventor
Jari Natunen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Biotie Therapies Corp
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2385295A1 publication Critical patent/CA2385295A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02Acyclic radicals, not substituted by cyclic structures
    • C07H15/12Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/203Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00Preparation of compounds containing saccharide radicals
    • C12P19/26Preparation of nitrogen-containing carbohydrates

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Polymers & Plastics (AREA)
  • Microbiology (AREA)
  • Materials Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Saccharide Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA002385295A 1999-09-28 2000-09-21 Novel fucosylated oligosaccharides and process for their preparation Abandoned CA2385295A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FI19992070A FI19992070A7 (fi) 1999-09-28 1999-09-28 Uudet fukosyloidut oligosakkaridit ja menetelmä niiden valmistamiseksi
FI19992070 1999-09-28
PCT/FI2000/000803 WO2001023398A1 (en) 1999-09-28 2000-09-21 Novel fucosylated oligosaccharides and process for their preparation

Publications (1)

Publication Number Publication Date
CA2385295A1 true CA2385295A1 (en) 2001-04-05

Family

ID=8555359

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002385295A Abandoned CA2385295A1 (en) 1999-09-28 2000-09-21 Novel fucosylated oligosaccharides and process for their preparation

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)

* Cited by examiner, † Cited by third party
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
US7800057B2 (en) * 2007-06-01 2010-09-21 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
ES2439507T3 (es) * 2011-01-20 2014-01-23 Jennewein Biotechnologie Gmbh Fucosiltransferasas novedosas y sus aplicaciones
US8999698B2 (en) 2011-03-31 2015-04-07 Novozymes Biologicals, Inc. Competitive and effective bacterial strains
ES2574957T3 (es) 2011-09-08 2016-06-23 Novozymes Bioag A/S Métodos de tratamiento de semillas
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
CN104066327A (zh) 2011-09-23 2014-09-24 诺维信生物农业公司 用于增强植物生长的脂壳寡糖组合和方法
EP2747567B1 (en) 2011-09-23 2016-11-16 Novozymes Bioag A/S Chitooligosaccharides and methods for use in enhancing soybean growth
EP2747558B1 (en) 2011-09-23 2018-01-03 Novozymes Bioag A/S Use of chitooligosaccharides in a method for enhancing plant growth
BR112014006912A2 (pt) 2011-09-23 2017-04-11 Novozymes Bioag As método para intensificar o crescimento de plantas de milho
AU2012351899B2 (en) 2011-12-16 2015-04-23 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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992016640A1 (en) 1991-03-18 1992-10-01 The Scripps Research Institute Oligosaccharide enzyme substrates and inhibitors: methods and compositions
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
WO1997003206A1 (en) * 1995-07-13 1997-01-30 Bioflexin Ab Method of producing derivatives of glc-beta 1-4glc-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

Also Published As

Publication number Publication date
DE60013161T2 (de) 2005-12-29
AU7293000A (en) 2001-04-30
AU780370B2 (en) 2005-03-17
WO2001023398A1 (en) 2001-04-05
FI19992070L (fi) 2001-03-28
JP2003510330A (ja) 2003-03-18
FI19992070A7 (fi) 2001-03-29
NZ518267A (en) 2003-10-31
US6878819B1 (en) 2005-04-12
ZA200202184B (en) 2003-05-28
DE60013161D1 (de) 2004-09-23
EP1228079B1 (en) 2004-08-18
ATE273987T1 (de) 2004-09-15
EP1228079A1 (en) 2002-08-07

Similar Documents

Publication Publication Date Title
AU780370B2 (en) Novel fucosylated oligosaccharides and process for their preparation
Sabesan et al. Combined chemical and enzymatic synthesis of sialyloligosaccharides and characterization by 500-MHz and proton and carbon-13 NMR spectroscopy
Niemelä et al. Complementary acceptor and site specificities of Fuc-TIV and Fuc-TVII allow effective biosynthesis of sialyl-TriLex and related polylactosamines present on glycoprotein counterreceptors of selectins
JP6602747B2 (ja) 同位体標識されたグリカンの合成および使用
Spillmann et al. Characterization of a novel sulfated carbohydrate unit implicated in the carbohydrate-carbohydrate-mediated cell aggregation of the marine sponge Microciona prolifera
Palcic et al. Transfer of D-galactosyl groups to 6-O-substituted 2-acetamido-2-deoxy-D-glucose residues by use of bovine D-galactosyltransferase
Rich et al. Chemical and Chemoenzymatic Synthesis of S‐Linked Ganglioside Analogues and Their Protein Conjugates for Use as Immunogens
Spillmann et al. Characterization of a novel pyruvylated carbohydrate unit implicated in the cell aggregation of the marine sponge Microciona prolifera
Chen et al. Sequence determination of a non-sulfated glycosaminoglycan-like polysaccharide from melanin-free ink of the squid Ommastrephes bartrami by negative-ion electrospray tandem mass spectrometry and NMR spectroscopy
Harvey Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for the period 2005–2006
Kochetkov et al. Synthesis of the O-antigenic polysaccharide of Salmonella newington and of its analogue differing in configuration at the only glycosidic centre
Haishima et al. Structural investigation on the lipopolysaccharide of Escherichia coli rough mutant F653 representing the R3 core type
Paul et al. Sequence of the halobacterial glycosaminoglycan.
US5426178A (en) Synthesis of anti-inflammatory compounds, and novel trisaccharides useful in the synthesis of anti-inflammatory compounds
Wakabayashi et al. Novel proteoglycan linkage tetrasaccharides of human urinary soluble thrombomodulin, SO4-3GlcAβ1–3Galβ1–3 (±Siaα2–6) Galβ1–4Xyl
Warner et al. Structure analysis of the major oligosaccharides accumulating in canine GM1 gangliosidosis liver.
McIntire et al. Structure of a new hexasaccharide from the coaggregation polysaccharide of Streptococcus sanguis 34
Fritz et al. Partial purification and substrate specificity of heparan sulfate α-N-acetylglucosaminyltransferase I: synthesis, NMR spectroscopic characterization and in vitro assays of two aryl tetrasaccharides
Cox et al. Structural analysis of the lipopolysaccharide from Vibrio cholerae serotype O22
Kwase et al. Protecting‐Group‐Free Glycoconjugate Synthesis: Hydrazide and Oxyamine Derivatives in N‐Glycoside Formation
Krotkiewski et al. Structural analysis by fast-atom-bombardment mass spectrometry of the mixture of alditols derived from the O-linked oligosaccharides of murine glycophorins
US20080081905A1 (en) Preparation and uses of locked-ring sugar C-glycoside derivatives
Zhang et al. Synthesis of the tolerance‐inducing oligosaccharide lacto‐N‐fucopentaose III bearing an activated linker
Salminen et al. Improved enzymatic synthesis of a highly potent oligosaccharide antagonist of L-selectin
Tamura et al. Synthesis of β-GlcA-(1→ 3)-β-Gal and α-GalNAc-(1→ 4)-β-GleA-(1→ 3)-β-Gal as Biotinylated 2-Aminoethyl Glycoside and the Streptavidin Complex Formation

Legal Events

Date Code Title Description
EEER Examination request
FZDE Discontinued
FZDE Discontinued

Effective date: 20101108