CA2110386A1 - Method for the Enzymatic Synthesis of Alpha-Sialylated Oligosaccharide Glycosides - Google Patents

Method for the Enzymatic Synthesis of Alpha-Sialylated Oligosaccharide Glycosides

Info

Publication number
CA2110386A1
CA2110386A1 CA2110386A CA2110386A CA2110386A1 CA 2110386 A1 CA2110386 A1 CA 2110386A1 CA 2110386 A CA2110386 A CA 2110386A CA 2110386 A CA2110386 A CA 2110386A CA 2110386 A1 CA2110386 A1 CA 2110386A1
Authority
CA
Canada
Prior art keywords
alpha
enzymatic synthesis
sialylated oligosaccharide
employed
oligosaccharide glycosides
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.)
Granted
Application number
CA2110386A
Other languages
French (fr)
Other versions
CA2110386C (en
Inventor
Andre P. Venot
Frank M. Unger
Mohammed A. Kashem
Paul Bird
M. Abdul Mazid
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.)
Glycomed Inc
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 CA2110386A1 publication Critical patent/CA2110386A1/en
Application granted granted Critical
Publication of CA2110386C publication Critical patent/CA2110386C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/26—Preparation of nitrogen-containing carbohydrates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Saccharide Compounds (AREA)
  • Immobilizing And Processing Of Enzymes And Microorganisms (AREA)

Abstract

Disclosed are methods for the enzymatic synthesis of alpha-sialylated oligosaccharide glycosides: Specifically, in the disclosed methods, sialyltransferase is activated to transfer an analogue of sialic acid, employed as its CMP-nucleotide derivative, to an oligosaccharide glycoside. The analogue of sialic acid and the oligosaccharide employed in this method are selected to be compatible with the sialyltransferase employed.
CA002110386A 1991-06-10 1992-06-09 Method for the enzymatic synthesis of alpha-sialylated oligosaccharide glycosides Expired - Fee Related CA2110386C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US71416191A 1991-06-10 1991-06-10
US07/714,161 1991-06-10
US07/771,007 US5352670A (en) 1991-06-10 1991-10-02 Methods for the enzymatic synthesis of alpha-sialylated oligosaccharide glycosides
US07/771,007 1991-10-02
PCT/CA1992/000243 WO1992022661A1 (en) 1991-06-10 1992-06-09 Methods for the enzymatic synthesis of alpha-sialylated oligosaccharide glycosides

Publications (2)

Publication Number Publication Date
CA2110386A1 true CA2110386A1 (en) 1992-12-23
CA2110386C CA2110386C (en) 2000-04-25

Family

ID=27109106

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002110386A Expired - Fee Related CA2110386C (en) 1991-06-10 1992-06-09 Method for the enzymatic synthesis of alpha-sialylated oligosaccharide glycosides

Country Status (8)

Country Link
US (1) US5352670A (en)
EP (1) EP0589933B1 (en)
JP (1) JPH06509703A (en)
AT (1) ATE148920T1 (en)
CA (1) CA2110386C (en)
DE (1) DE69217491T2 (en)
ES (1) ES2100346T3 (en)
WO (1) WO1992022661A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115343485A (en) * 2022-10-18 2022-11-15 天津德祥生物技术股份有限公司 Application of blood group antigen-trisaccharide conjugate in blood group antibody detection

Families Citing this family (122)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5079353A (en) * 1987-12-02 1992-01-07 Chembiomed, Ltd. Sialic acid glycosides, antigens, immunoadsorbents, and methods for their preparation
JPH06510744A (en) * 1991-06-10 1994-12-01 グライカムド　インコーポレイテッド Modified sialyl Lewis x compound
EP0588848A1 (en) * 1991-06-10 1994-03-30 Glycomed Incorporated Modified sialyl lewis?a compounds
JPH07500248A (en) 1991-10-15 1995-01-12 ザ スクリップス リサーチ インスティテュート Production of fucosylated carbohydrates by enzymatic fucosylation synthesis of sugar nucleotides and in situ regeneration of GDP-fucose
WO1994010340A1 (en) * 1992-10-30 1994-05-11 Mt. Sinai Hospital Corporation Method for measuring glycosyltransferase activity
US6406894B1 (en) 1992-12-11 2002-06-18 Glycorex Ab Process for preparing polyvalent and physiologically degradable carbohydrate-containing polymers by enzymatic glycosylation reactions and the use thereof for preparing carbohydrate building blocks
SK141695A3 (en) * 1993-05-14 1996-10-02 Cytel Corp Analogous compound sialyl lex, pharmaceutical agent containing this compound and method of preparation of lactoseammoniacal salt
US5811404A (en) * 1993-05-14 1998-09-22 Cytel Corporation Sialyl Lex analogues as inhibitors of cellular adhesion
US5854218A (en) * 1993-05-14 1998-12-29 Cytel Corporation Sialyl Lex analogues as inhibitors of cellular adhesion
US5559103A (en) * 1993-07-21 1996-09-24 Cytel Corporation Bivalent sialyl X saccharides
DE4431280A1 (en) 1994-09-02 1996-03-07 Hoechst Ag Process for the isolation and purification of nucleotide-activated sugars from biological sources
US5545553A (en) * 1994-09-26 1996-08-13 The Rockefeller University Glycosyltransferases for biosynthesis of oligosaccharides, and genes encoding them
US6030815A (en) * 1995-04-11 2000-02-29 Neose Technologies, Inc. Enzymatic synthesis of oligosaccharides
US5876980A (en) * 1995-04-11 1999-03-02 Cytel Corporation Enzymatic synthesis of oligosaccharides
US5728554A (en) * 1995-04-11 1998-03-17 Cytel Corporation Enzymatic synthesis of glycosidic linkages
US5922577A (en) * 1995-04-11 1999-07-13 Cytel Corporation Enzymatic synthesis of glycosidic linkages
EP0874861A1 (en) * 1995-09-29 1998-11-04 Glycim Oy Synthetic multivalent slex containing polylactosamines and methods for use
AUPN658795A0 (en) * 1995-11-15 1995-12-07 Commonwealth Scientific And Industrial Research Organisation Method of producing alpha 2, 3 sialyltransferase
US6841543B1 (en) * 1996-01-31 2005-01-11 President And Fellows Of Harvard College Methods of inhibiting production of T helper type 2 cytokines in human immune cells
US6033663A (en) * 1996-04-10 2000-03-07 Neose Technologies, Inc. Nucleic acids encoding GDP-Fucose pyrophosphorylase
WO1998015581A1 (en) 1996-10-10 1998-04-16 Cytel Corporation Carbohydrate purification using ultrafiltration, reverse osmosis and nanofiltration
WO1998031826A1 (en) * 1997-01-16 1998-07-23 Cytel Corporation Practical in vitro sialylation of recombinant glycoproteins
AU9073998A (en) 1997-09-05 1999-03-29 Glycim Oy Synthetic divalent slex containing polylactosamines and methods for use
EP1903114A3 (en) 1997-12-01 2008-07-23 Neose Technologies, Inc. Enzymatic synthesis of gangliosides
US7244601B2 (en) * 1997-12-15 2007-07-17 National Research Council Of Canada Fusion proteins for use in enzymatic synthesis of oligosaccharides
US6500661B1 (en) 1998-01-15 2002-12-31 Neose Technologies, Inc. Enzymatic conversion of GDP-mannose to GDP-fucose
US6689604B1 (en) * 1998-03-20 2004-02-10 National Research Council Of Canada Lipopolysaccharide α-2,3 sialyltransferase of Campylobacter jejuni and its uses
US6194178B1 (en) 1998-09-03 2001-02-27 Synsorb Biotech Inc. Method for the production of sialylated oligosaccharides
US6503744B1 (en) * 1999-02-01 2003-01-07 National Research Council Of Canada Campylobacter glycosyltransferases for biosynthesis of gangliosides and ganglioside mimics
US6699705B2 (en) * 1999-02-01 2004-03-02 National Research Council Of Canada Campylobacter glycosyltransferases for biosynthesis of gangliosides and ganglioside mimics
EP1311550A2 (en) * 2000-08-22 2003-05-21 National Research Council Of Canada Synthesis of complex carbohydrates
AU2002330968B2 (en) 2001-08-17 2007-03-22 Neose Technologies, Inc. Chemo-enzymatic synthesis of sialylated oligosaccharides
US7226903B2 (en) * 2001-10-10 2007-06-05 Neose Technologies, Inc. Interferon beta: remodeling and glycoconjugation of interferon beta
US7399613B2 (en) * 2001-10-10 2008-07-15 Neose Technologies, Inc. Sialic acid nucleotide sugars
NZ532027A (en) * 2001-10-10 2008-09-26 Neose Technologies Inc Remodeling and glycoconjugation of peptides
US8008252B2 (en) * 2001-10-10 2011-08-30 Novo Nordisk A/S Factor VII: remodeling and glycoconjugation of Factor VII
US7795210B2 (en) 2001-10-10 2010-09-14 Novo Nordisk A/S Protein remodeling methods and proteins/peptides produced by the methods
US7179617B2 (en) 2001-10-10 2007-02-20 Neose Technologies, Inc. Factor IX: remolding and glycoconjugation of Factor IX
US7696163B2 (en) 2001-10-10 2010-04-13 Novo Nordisk A/S Erythropoietin: remodeling and glycoconjugation of erythropoietin
US7214660B2 (en) 2001-10-10 2007-05-08 Neose Technologies, Inc. Erythropoietin: remodeling and glycoconjugation of erythropoietin
CN105131104B (en) 2001-10-10 2018-11-16 诺和诺德公司 The reconstruct and sugar conjugation of peptide
US7173003B2 (en) 2001-10-10 2007-02-06 Neose Technologies, Inc. Granulocyte colony stimulating factor: remodeling and glycoconjugation of G-CSF
US7265085B2 (en) * 2001-10-10 2007-09-04 Neose Technologies, Inc. Glycoconjugation methods and proteins/peptides produced by the methods
US7297511B2 (en) * 2001-10-10 2007-11-20 Neose Technologies, Inc. Interferon alpha: remodeling and glycoconjugation of interferon alpha
US7125843B2 (en) * 2001-10-19 2006-10-24 Neose Technologies, Inc. Glycoconjugates including more than one peptide
US7157277B2 (en) * 2001-11-28 2007-01-02 Neose Technologies, Inc. Factor VIII remodeling and glycoconjugation of Factor VIII
US7265084B2 (en) * 2001-10-10 2007-09-04 Neose Technologies, Inc. Glycopegylation methods and proteins/peptides produced by the methods
US7439043B2 (en) * 2001-10-10 2008-10-21 Neose Technologies, Inc. Galactosyl nucleotide sugars
US7473680B2 (en) * 2001-11-28 2009-01-06 Neose Technologies, Inc. Remodeling and glycoconjugation of peptides
AU2003267949A1 (en) * 2002-03-15 2003-12-31 U.S. Government As Represented By The Department Of Veterans Affairs Methods and compositions using cellular asialodeterminants and glycoconjugates for targeting cells to tissues and organs
US7060685B2 (en) * 2002-05-16 2006-06-13 Glycomimetics, Inc. Compounds and methods for inhibiting selectin-mediated function
DE60336555D1 (en) 2002-06-21 2011-05-12 Novo Nordisk Healthcare Ag PEGYLATED GLYCO FORMS OF FACTOR VII
WO2004004636A2 (en) * 2002-07-03 2004-01-15 Glycomimetics, Inc. Compositions and methods for diagnosis and therapy of medical conditions involving angiogenesis
CN1711475A (en) * 2002-10-10 2005-12-21 退伍军人事务部 Detection, localization and staging of tumors using labeled activated lymphocytes directed to a tumor specific epitope
BRPI0316018B8 (en) 2002-11-12 2021-05-25 Brigham & Womens Hospital Inc polysaccharide vaccine for staphylococcal infections
JP2006519878A (en) 2003-03-06 2006-08-31 ネオーズ テクノロジーズ， インコーポレイテッド Methods and compounds for enzymatic synthesis of gangliosides
KR20060003862A (en) 2003-03-14 2006-01-11 네오스 테크놀로지스, 인크. Branched water-soluble polymers and their eonjugates
US7691603B2 (en) * 2003-04-09 2010-04-06 Novo Nordisk A/S Intracellular formation of peptide conjugates
US20070026485A1 (en) 2003-04-09 2007-02-01 Neose Technologies, Inc. Glycopegylation methods and proteins/peptides produced by the methods
WO2006127896A2 (en) * 2005-05-25 2006-11-30 Neose Technologies, Inc. Glycopegylated factor ix
US8791070B2 (en) 2003-04-09 2014-07-29 Novo Nordisk A/S Glycopegylated factor IX
US20040219158A1 (en) * 2003-05-02 2004-11-04 Glycomimetics, Inc. Compositions and methods for diagnosis and therapy of medical conditions involving infection with pseudomonas bacteria
US7932364B2 (en) 2003-05-09 2011-04-26 Novo Nordisk A/S Compositions and methods for the preparation of human growth hormone glycosylation mutants
WO2005012484A2 (en) 2003-07-25 2005-02-10 Neose Technologies, Inc. Antibody-toxin conjugates
WO2005016974A1 (en) * 2003-08-12 2005-02-24 Lipoxen Technologies Limited Sialic acid derivatives for protein derivatisation and conjugation
WO2005051920A2 (en) * 2003-11-19 2005-06-09 Glycomimetics, Inc. Specific antagonist for both e- and p-selectins
JP2007524658A (en) * 2003-11-19 2007-08-30 グリコミメティクス， インコーポレイテッド Glucose mimetic antagonists for both E- and P-selectin
US8633157B2 (en) 2003-11-24 2014-01-21 Novo Nordisk A/S Glycopegylated erythropoietin
EP1694347B1 (en) * 2003-11-24 2013-11-20 BioGeneriX AG Glycopegylated erythropoietin
US20080305992A1 (en) 2003-11-24 2008-12-11 Neose Technologies, Inc. Glycopegylated erythropoietin
US7956032B2 (en) * 2003-12-03 2011-06-07 Novo Nordisk A/S Glycopegylated granulocyte colony stimulating factor
US20080318850A1 (en) * 2003-12-03 2008-12-25 Neose Technologies, Inc. Glycopegylated Factor Ix
US20060040856A1 (en) * 2003-12-03 2006-02-23 Neose Technologies, Inc. Glycopegylated factor IX
KR101439880B1 (en) 2004-01-08 2014-09-12 라티오팜 게엠베하 O-linked glycosylation of peptides
EP2484759B1 (en) 2004-02-04 2014-06-25 ratiopharm GmbH Methods of refolding mammalian glycosyltransferases
ATE455861T1 (en) 2004-05-04 2010-02-15 Novo Nordisk Healthcare Ag O-LINKED GLYCOFORMS OF FACTOR VII AND METHOD FOR THE PRODUCTION THEREOF
EP1771066A2 (en) 2004-07-13 2007-04-11 Neose Technologies, Inc. Branched peg remodeling and glycosylation of glucagon-like peptide-1 glp-1
US8268967B2 (en) 2004-09-10 2012-09-18 Novo Nordisk A/S Glycopegylated interferon α
JP2008514215A (en) * 2004-09-29 2008-05-08 ノボ ノルディスク ヘルス ケア アクチェンゲゼルシャフト Modified protein
ES2572779T3 (en) 2004-10-29 2016-06-02 Ratiopharm Gmbh Remodeling and glucopegilation of Fibroblast Growth Factor (FGF)
ES2449195T3 (en) 2005-01-10 2014-03-18 Ratiopharm Gmbh Glycopegylated granulocyte colony stimulating factor
US20060246544A1 (en) * 2005-03-30 2006-11-02 Neose Technologies,Inc. Manufacturing process for the production of peptides grown in insect cell lines
EP2386571B1 (en) 2005-04-08 2016-06-01 ratiopharm GmbH Compositions and methods for the preparation of protease resistant human growth hormone glycosylation mutants
EP1888098A2 (en) 2005-05-25 2008-02-20 Neose Technologies, Inc. Glycopegylated erythropoietin formulations
US20090036386A1 (en) * 2005-05-25 2009-02-05 Glycomimetics, Inc Heterobifunctional compounds for selectin inhibition
DK1928892T3 (en) * 2005-08-09 2012-01-30 Glycomimetics Inc Glycomimetic inhibitors of PA-IL lectin PA-IIL lectin or both pseudomonas lectins
KR20080080081A (en) * 2005-08-19 2008-09-02 네오스 테크놀로지스, 인크. Glycopegylated factor vii and factor viia
US20070105755A1 (en) * 2005-10-26 2007-05-10 Neose Technologies, Inc. One pot desialylation and glycopegylation of therapeutic peptides
PL1934236T3 (en) 2005-09-02 2013-04-30 Glycomimetics Inc Heterobifunctional pan-selectin inhibitors
US20090048440A1 (en) * 2005-11-03 2009-02-19 Neose Technologies, Inc. Nucleotide Sugar Purification Using Membranes
US20090176717A1 (en) * 2006-06-01 2009-07-09 Glycomimetics, Inc. Galactosides and thiodigalactosides as inhibitors of pa-il lectin from pseudomonas
US9187532B2 (en) 2006-07-21 2015-11-17 Novo Nordisk A/S Glycosylation of peptides via O-linked glycosylation sequences
EP2054521A4 (en) 2006-10-03 2012-12-19 Novo Nordisk As Methods for the purification of polypeptide conjugates
JP5457185B2 (en) 2006-10-04 2014-04-02 ノヴォ ノルディスク アー／エス Glycerol-linked PEGylated sugars and glycopeptides
JP5298020B2 (en) 2006-10-12 2013-09-25 グリコミメティクス， インコーポレイテッド Glucose mimic substitution of hexose and N-acetylhexosamine
WO2008073620A2 (en) * 2006-11-02 2008-06-19 Neose Technologies, Inc. Manufacturing process for the production of polypeptides expressed in insect cell-lines
AU2008216794A1 (en) * 2007-02-09 2008-08-21 Glycomimetics, Inc. Methods of use of glycomimetics with replacements for hexoses and N-acetyl hexosamines
CA2682897C (en) 2007-04-03 2016-11-22 Biogenerix Ag Methods of treatment using glycopegylated g-csf
US20090053167A1 (en) * 2007-05-14 2009-02-26 Neose Technologies, Inc. C-, S- and N-glycosylation of peptides
CN101778859B (en) 2007-06-12 2014-03-26 诺和诺德公司 Improved process for the production of nucleotide sugars
US8039442B2 (en) * 2007-07-18 2011-10-18 Glycomimetics, Inc. Compounds and methods for treatment of sickle cell disease or complications associated therewith
US8207112B2 (en) 2007-08-29 2012-06-26 Biogenerix Ag Liquid formulation of G-CSF conjugate
US20130189239A1 (en) 2008-02-27 2013-07-25 Novo Nordisk A/S Conjugated Factor VIII Molecules
WO2009126556A1 (en) 2008-04-08 2009-10-15 Glycomimetics, Inc. Pan-selectin inhibitor with enhanced pharmacokinetic activity
JP2011522805A (en) 2008-05-30 2011-08-04 モメンタ ファーマシューティカルズ インコーポレイテッド Sugar structures and methods of making and using such structures
EP2318015B1 (en) * 2008-06-13 2013-08-07 GlycoMimetics, Inc. Treatment of cancers of the blood using selected glycomimetic compounds
BRPI0916365A2 (en) 2008-07-21 2018-05-02 Brigham & Womens Hospital Inc methods and compositions related to synthetic beta-1,6 glycosine oligosaccharides
JP5726171B2 (en) * 2009-05-01 2015-05-27 グリコミメティックス インコーポレイテッド Heterobifunctional inhibitors of E-selectin and CXCR4 chemokine receptors
US8921328B2 (en) 2010-09-14 2014-12-30 Glycomimetics, Inc. E-selectin antagonists
WO2013096926A1 (en) 2011-12-22 2013-06-27 Glycomimetics, Inc. E-selectin antagonist compounds, compositions, and methods of use
EP2698636A1 (en) * 2012-08-13 2014-02-19 Fundació Institut d'Investigació Biomèdica de Bellvitge Methods and reagents for prevention and/or treatment of transplant rejection
LT2928476T (en) 2012-12-07 2018-05-25 Glycomimetics, Inc. Compounds, compositions and methods using e-selectin antagonists for mobilization of hematopoietic cells
SI3227310T1 (en) 2014-12-03 2019-11-29 Glycomimetics Inc Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors
WO2017127422A1 (en) 2016-01-22 2017-07-27 Glycomimetics, Inc. Glycomimetic inhibitors of pa-il and pa-iil lectins
US11291678B2 (en) 2016-03-02 2022-04-05 Glycomimetics, Inc Methods for the treatment and/or prevention of cardiovascular disease by inhibition of E-selectin
JP2019524791A (en) 2016-08-08 2019-09-05 グリコミメティクス， インコーポレイテッド Combinations of T cell checkpoint inhibitors with inhibitors of E-selectin or inhibitors of CXCR4 or with heterobifunctional inhibitors of both E-selectin and CXCR4
KR20240046288A (en) 2016-10-07 2024-04-08 글리코미메틱스, 인크. Highly potent multimeric e-selectin antagonists
CA3054605A1 (en) 2017-03-15 2018-09-20 Glycomimetics, Inc. Galactopyranosyl-cyclohexyl derivatives as e-selectin antagonists
WO2019108750A1 (en) 2017-11-30 2019-06-06 Glycomimetics, Inc. Methods of mobilizing marrow infiltrating lymphocytes and uses thereof
JP7304863B2 (en) 2017-12-29 2023-07-07 グリコミメティクス， インコーポレイテッド Heterobifunctional inhibitors of E-selectin and galectin-3
US11707474B2 (en) 2018-03-05 2023-07-25 Glycomimetics, Inc. Methods for treating acute myeloid leukemia and related conditions
US11845771B2 (en) 2018-12-27 2023-12-19 Glycomimetics, Inc. Heterobifunctional inhibitors of E-selectin and galectin-3

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1544908A (en) * 1975-07-08 1979-04-25 Chembiomed Ltd Artificial oligosaccharide antigenic determinants
GB1603609A (en) * 1977-04-14 1981-11-25 Chembiomed Ltd O-protected 2-azido-2-deoxy-glycosyl nitrates
US4727136A (en) * 1985-10-01 1988-02-23 Canadian Patents And Development Ltd. Modified meningococcal group B polysaccharide for conjugate vaccine
US5079353A (en) * 1987-12-02 1992-01-07 Chembiomed, Ltd. Sialic acid glycosides, antigens, immunoadsorbents, and methods for their preparation
US5032505A (en) * 1988-11-21 1991-07-16 Chembiomed, Ltd. Inhibitors for glycosaminosyl transferase V
US5047335A (en) * 1988-12-21 1991-09-10 The Regents Of The University Of Calif. Process for controlling intracellular glycosylation of proteins
US5070021A (en) * 1989-01-10 1991-12-03 Monsanto Company Method of modifying oligosaccharide structure of tissue plasminogen activator
US5059535A (en) * 1989-04-12 1991-10-22 Chembiomed, Ltd. Process for the separation and purification of sialyl transferases
EP0395217A3 (en) * 1989-04-28 1991-01-23 The Biomembrane Institute Bio-organic synthesis of dimeric lex (difucosyl y2; iii3fucv3-funcnlc6cer) and analogues thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115343485A (en) * 2022-10-18 2022-11-15 天津德祥生物技术股份有限公司 Application of blood group antigen-trisaccharide conjugate in blood group antibody detection
CN115343485B (en) * 2022-10-18 2023-01-06 天津德祥生物技术股份有限公司 Application of blood group antigen-trisaccharide conjugate in blood group antibody detection

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ES2100346T3 (en) 1997-06-16
JPH06509703A (en) 1994-11-02
EP0589933B1 (en) 1997-02-12
DE69217491T2 (en) 1997-10-02
US5352670A (en) 1994-10-04
CA2110386C (en) 2000-04-25
WO1992022661A1 (en) 1992-12-23
DE69217491D1 (en) 1997-03-27
EP0589933A1 (en) 1994-04-06

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