WO2000020428A3 - Synthesis of oligosaccharides, reagents and methods related thereto - Google Patents

Synthesis of oligosaccharides, reagents and methods related thereto Download PDF

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Publication number
WO2000020428A3
WO2000020428A3 PCT/US1999/023292 US9923292W WO0020428A3 WO 2000020428 A3 WO2000020428 A3 WO 2000020428A3 US 9923292 W US9923292 W US 9923292W WO 0020428 A3 WO0020428 A3 WO 0020428A3
Authority
WO
WIPO (PCT)
Prior art keywords
oligosaccharides
reagents
synthesis
methods related
present
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.)
Ceased
Application number
PCT/US1999/023292
Other languages
French (fr)
Other versions
WO2000020428A9 (en
WO2000020428A2 (en
Inventor
Peter H Seeberger
Obadiah J Plante
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.)
Massachusetts Institute of Technology
Original Assignee
Massachusetts Institute of Technology
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 Massachusetts Institute of Technology filed Critical Massachusetts Institute of Technology
Priority to CA002346237A priority Critical patent/CA2346237A1/en
Priority to EP99951811A priority patent/EP1119577B1/en
Priority to JP2000574539A priority patent/JP2002526549A/en
Priority to DE69935344T priority patent/DE69935344D1/en
Publication of WO2000020428A2 publication Critical patent/WO2000020428A2/en
Publication of WO2000020428A3 publication Critical patent/WO2000020428A3/en
Publication of WO2000020428A9 publication Critical patent/WO2000020428A9/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
    • C07H5/06—Aminosugars
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
    • C07H11/04—Phosphates; Phosphites; Polyphosphates
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00596—Solid-phase processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/0068—Means for controlling the apparatus of the process
    • B01J2219/00686—Automatic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00718—Type of compounds synthesised
    • B01J2219/0072—Organic compounds
    • B01J2219/00731—Saccharides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/11—Compounds covalently bound to a solid support
    • C—CHEMISTRY; METALLURGY
    • C40—COMBINATORIAL TECHNOLOGY
    • C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
    • C40B40/00—Libraries per se, e.g. arrays, mixtures
    • C40B40/04—Libraries containing only organic compounds
    • C40B40/12—Libraries containing saccharides or polysaccharides, or derivatives thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Saccharide Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

One aspect of the present invention relates to differentially protected glycosyl phosphates. Another aspect of the present invention relates to the preparation of glycosyl phosphates from glycal precursors. In another aspect of the present invention, glycosyl phosphates are used as glycosyl donors in glycosylation reactions.
PCT/US1999/023292 1998-10-06 1999-10-06 Synthesis of oligosaccharides, reagents and methods related thereto Ceased WO2000020428A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002346237A CA2346237A1 (en) 1998-10-06 1999-10-06 Synthesis of oligosaccharides, reagents and methods related thereto
EP99951811A EP1119577B1 (en) 1998-10-06 1999-10-06 Synthesis of oligonucleotides, reagents and methods related thereto
JP2000574539A JP2002526549A (en) 1998-10-06 1999-10-06 Oligosaccharide synthesis, reagents and synthetic methods related thereto
DE69935344T DE69935344D1 (en) 1998-10-06 1999-10-06 Synthesis of oligosaccharides, reagents and processes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10329198P 1998-10-06 1998-10-06
US60/103,291 1998-10-06

Publications (3)

Publication Number Publication Date
WO2000020428A2 WO2000020428A2 (en) 2000-04-13
WO2000020428A3 true WO2000020428A3 (en) 2000-09-14
WO2000020428A9 WO2000020428A9 (en) 2000-10-26

Family

ID=22294418

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/023292 Ceased WO2000020428A2 (en) 1998-10-06 1999-10-06 Synthesis of oligosaccharides, reagents and methods related thereto

Country Status (7)

Country Link
US (2) US6323339B1 (en)
EP (1) EP1119577B1 (en)
JP (1) JP2002526549A (en)
AT (1) ATE355295T1 (en)
CA (1) CA2346237A1 (en)
DE (1) DE69935344D1 (en)
WO (1) WO2000020428A2 (en)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6538117B1 (en) * 1999-08-10 2003-03-25 The Scripps Research Institute Programmable one-pot oligosaccharide synthesis
EP1119577B1 (en) * 1998-10-06 2007-02-28 Massachusetts Institute Of Technology Synthesis of oligonucleotides, reagents and methods related thereto
IL129835A (en) * 1999-05-06 2008-03-20 Ofer Markman Polysaccharide sequencing and structure determination
CA2391966A1 (en) 1999-11-24 2001-05-31 Massachusetts Institute Of Technology Protecting groups useful in the synthesis of polysaccharides, natural products, and combinatorial libraries
WO2002016384A2 (en) * 2000-08-18 2002-02-28 Massachusetts Institute Of Technology Apparatus and methods for the automated synthesis of oligosaccharides
US20040132131A1 (en) * 2001-11-05 2004-07-08 Ofer Markman Methods for comparitive analysis of carbohydrate polymers and carbohydrate polymers identified using same
US6974665B2 (en) 2001-09-06 2005-12-13 University Of Nebraska In situ screening to optimize variables in organic reactions
MXPA05010949A (en) * 2003-04-11 2005-11-25 Pharmacia Italia Spa Fused oxabicyclic aminoalcohols as new scaffolds for combinatorial libraries.
FR2861730B1 (en) * 2003-10-31 2006-01-27 Fabre Pierre Dermo Cosmetique PROCESS FOR THE DIRECT SYNTHESIS OF OLIGORHAMNOSIDES, COMPOSITION COMPRISING OLIGORHAMNOSIDES AND USE AS A MEDICAMENT
US20050186645A1 (en) * 2003-12-18 2005-08-25 Yehudit Amor Method for analyzing a glycomolecule
US20060084630A1 (en) * 2004-10-07 2006-04-20 Ensley Harry E Method for synthesis of beta glucans
US8420607B2 (en) * 2006-06-30 2013-04-16 University Of Georgia Research Foundation, Inc. Anthrax carbohydrates, synthesis and uses thereof
AU2007349310B2 (en) 2006-06-30 2013-03-14 THE UNITED STATES OF AMERICA, as represented by THE SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES, CENTERS OF DISEASE CONTROL AND PREVENTION (WASHINGTON D.C.) Anthrax carbohydrates,synthesis and uses thereof
US20100266558A1 (en) * 2007-12-18 2010-10-21 Dov Zipori Method and assay for glycosylation pattern detection related to cell state of stem cells
US9399655B2 (en) 2012-06-06 2016-07-26 University of Pittsburgh—of the Commonwealth System of Higher Education Catalytic glycosylation with designer thioglycoside and novel protecting groups for same and for synthesis of oligosaccharides
EP2733358A1 (en) 2012-11-15 2014-05-21 ABB Oy Method for approximating the static head downstream of a pump
CN105461767B (en) * 2014-08-07 2019-03-12 富力 A kind of chemical synthesis process of forsythin
WO2021089623A1 (en) * 2019-11-04 2021-05-14 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Synthesizer for oligo- and polysaccharides on solid phase
EP3815778A1 (en) * 2019-11-04 2021-05-05 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Device for rapid automated synthesis of oligo- and polysaccharides

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4785084A (en) * 1986-07-31 1988-11-15 The General Hospital Corporation Method of preparing peracetyl oxazolines
US5095123A (en) * 1990-11-30 1992-03-10 E. I. Du Pont De Nemours And Company Process for the preparation of glycosyl phosphate triesters

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AU668505B2 (en) 1991-03-18 1996-05-09 Scripps Research Institute, The 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
US5516665A (en) 1993-09-13 1996-05-14 The Scripps Research Institute N-acetylgalactosaminyl or N-acetylglucosaminyl transfer using N-acetylglucosaminyl-1-phosphate or N-acetylgalactosaminyl-1-phosphate as precursor and glycosyl-nucleotide regeneration
US5369017A (en) 1994-02-04 1994-11-29 The Scripps Research Institute Process for solid phase glycopeptide synthesis
CA2189356A1 (en) 1994-05-02 1995-11-09 Ting Chi Wong Process for preparation of glycosides of tumor-associated carbohydrate antigens
DE4431280A1 (en) 1994-09-02 1996-03-07 Hoechst Ag Process for the isolation and purification of nucleotide-activated sugars from biological sources
AU4717296A (en) 1995-02-07 1996-08-27 Novartis Ag Process for the complete removal of protective groups on ncleoside diphosphate and triphosphate sugars
US6030815A (en) 1995-04-11 2000-02-29 Neose Technologies, Inc. Enzymatic synthesis of oligosaccharides
US5922577A (en) 1995-04-11 1999-07-13 Cytel Corporation Enzymatic synthesis of glycosidic linkages
US5728554A (en) 1995-04-11 1998-03-17 Cytel Corporation Enzymatic synthesis of glycosidic linkages
US6077695A (en) 1995-07-13 2000-06-20 Bioflexin Ab Method of producing derivatives of Glc-β 1-4Glc-N-acetyl
US5721338A (en) 1995-12-07 1998-02-24 California Institute Of Technology Inhibitors of oligosaccharyl transferase
US5716812A (en) 1995-12-12 1998-02-10 The University Of British Columbia Methods and compositions for synthesis of oligosaccharides, and the products formed thereby
JP3545424B2 (en) 1996-11-19 2004-07-21 ヤマサ醤油株式会社 Method for producing nucleoside 5'-triphosphate and its application
US5952203A (en) 1997-04-11 1999-09-14 The University Of British Columbia Oligosaccharide synthesis using activated glycoside derivative, glycosyl transferase and catalytic amount of nucleotide phosphate
WO1999028491A1 (en) 1997-12-01 1999-06-10 Cytel Corporation Enzymatic synthesis of gangliosides
US5952454A (en) 1997-12-12 1999-09-14 The United States Of America As Represented By The Department Of Health And Human Services Linking compounds useful for coupling carbohydrates to amine-containing carriers
DE19812162A1 (en) 1998-03-20 1999-09-30 Forschungszentrum Juelich Gmbh Nucleotide-activated di- and oligosaccharides and process for their preparation I
DE19812156A1 (en) 1998-03-20 1999-09-30 Forschungszentrum Juelich Gmbh Nucleotide-activated di- and oligosaccharides and process for their preparation II
EP1119577B1 (en) * 1998-10-06 2007-02-28 Massachusetts Institute Of Technology Synthesis of oligonucleotides, reagents and methods related thereto
CA2391966A1 (en) * 1999-11-24 2001-05-31 Massachusetts Institute Of Technology Protecting groups useful in the synthesis of polysaccharides, natural products, and combinatorial libraries

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
US4785084A (en) * 1986-07-31 1988-11-15 The General Hospital Corporation Method of preparing peracetyl oxazolines
US5095123A (en) * 1990-11-30 1992-03-10 E. I. Du Pont De Nemours And Company Process for the preparation of glycosyl phosphate triesters

Non-Patent Citations (9)

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C.M. TIMMERS, N.C.R. VAN STRATEN, G.A. VAN DER MAREL, J.H. VAN BOOM: "An expeditious route to streptococci and enterococci glycolipids via ring-opening of 1,2-anhydrosugars with protic acids", J. CARBOHYDRATE CHEMISTRY, vol. 17, no. 3, 1998, pages 471 - 487, XP002135533 *
H. PAULSEN, M. PRIES, J.P. LORENTZEN: "Synthese von DD-Heptosephosphaten als Substrate oder potentielle Inhibitoren für die Heptose-Synthetase", LIEBIGS ANN. CHEM., 1994, pages 389 - 397, XP002135530 *
HASHIMOTO S -I ET AL: ""Armed-Disarmed" Glycosidation Strategy Based on Glycosyl Donors and Acceptors Carrying Phosphoroamidate as a Leaving Group: A Convergent Synthesis of Globotriaosylceramide", TETRAHEDRON LETTERS,NL,ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, vol. 38, no. 52, 29 December 1997 (1997-12-29), pages 8969 - 8972, XP004098134, ISSN: 0040-4039 *
L. LAUPICHLER, H. SAJUS, J. THIEM: "Convenient iodonium-promoted stereoselective synthesis of 2-deoxy-alpha-glycosides by use of S-(2-deoxyglycosyl) phosphorodithioates as donors", SYNTHESIS, 1992, pages 1133 - 1136, XP002135534 *
M.-J. CHEN, K. RAVINDRAN, D.W.LANDRY, K. ZHAO: "Glycosyl phosphoramidimidates as versatile glycosyl donors", HETEROCYCLES, vol. 45, no. 7, 1997, pages 1247 - 1250, XP002135532 *
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Also Published As

Publication number Publication date
EP1119577A2 (en) 2001-08-01
WO2000020428A9 (en) 2000-10-26
ATE355295T1 (en) 2006-03-15
WO2000020428A2 (en) 2000-04-13
CA2346237A1 (en) 2000-04-13
US6323339B1 (en) 2001-11-27
US20030004322A1 (en) 2003-01-02
EP1119577B1 (en) 2007-02-28
DE69935344D1 (en) 2007-04-12
US7211663B2 (en) 2007-05-01
JP2002526549A (en) 2002-08-20

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