WO2007001282A3 - Low molecular weight polyglucosamines and polygalactosamines - Google Patents

Low molecular weight polyglucosamines and polygalactosamines Download PDF

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Publication number
WO2007001282A3
WO2007001282A3 PCT/US2005/022115 US2005022115W WO2007001282A3 WO 2007001282 A3 WO2007001282 A3 WO 2007001282A3 US 2005022115 W US2005022115 W US 2005022115W WO 2007001282 A3 WO2007001282 A3 WO 2007001282A3
Authority
WO
WIPO (PCT)
Prior art keywords
molecular weight
low molecular
polygalactosamines
polyglucosamines
compositions
Prior art date
Application number
PCT/US2005/022115
Other languages
French (fr)
Other versions
WO2007001282A2 (en
Inventor
Subramaniam Sabesan
Original Assignee
Du Pont
Subramaniam Sabesan
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
Priority claimed from US11/154,193 external-priority patent/US20060286149A1/en
Priority claimed from US11/154,457 external-priority patent/US7485718B2/en
Application filed by Du Pont, Subramaniam Sabesan filed Critical Du Pont
Publication of WO2007001282A2 publication Critical patent/WO2007001282A2/en
Publication of WO2007001282A3 publication Critical patent/WO2007001282A3/en

Links

Classifications

    • 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
    • A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • 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
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • 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
    • 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
    • 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
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • 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
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0087—Glucomannans or galactomannans; Tara or tara gum, i.e. D-mannose and D-galactose units, e.g. from Cesalpinia spinosa; Tamarind gum, i.e. D-galactose, D-glucose and D-xylose units, e.g. from Tamarindus indica; Gum Arabic, i.e. L-arabinose, L-rhamnose, D-galactose and D-glucuronic acid units, e.g. from Acacia Senegal or Acacia Seyal; Derivatives thereof

Abstract

Compositions containing enriched populations of beta linked low molecular weight polymers of galactosamine and glucosamine are provided. The compositions are useful, for example, as antibacterial additives for food and other edible applications, as precursors for synthesizing other biologically active molecules related to chitin/chitosan oligomers, and/or as pharmaceutical compounds.
PCT/US2005/022115 2005-06-16 2005-06-21 Low molecular weight polyglucosamines and polygalactosamines WO2007001282A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US11/154,193 2005-06-16
US11/154,193 US20060286149A1 (en) 2005-06-16 2005-06-16 Low molecular weight polyglucosamines and polygalactosamines
US11/154,457 US7485718B2 (en) 2005-06-16 2005-06-16 Chemical synthesis of low molecular weight polyglucosamines and polygalactosamines
US11/154,457 2005-06-16

Publications (2)

Publication Number Publication Date
WO2007001282A2 WO2007001282A2 (en) 2007-01-04
WO2007001282A3 true WO2007001282A3 (en) 2007-06-21

Family

ID=37595545

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/US2005/022116 WO2007001283A2 (en) 2005-06-16 2005-06-21 Chemical synthesis of low molecular weight polyglucosamines and polygalactosamines
PCT/US2005/022115 WO2007001282A2 (en) 2005-06-16 2005-06-21 Low molecular weight polyglucosamines and polygalactosamines

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/US2005/022116 WO2007001283A2 (en) 2005-06-16 2005-06-21 Chemical synthesis of low molecular weight polyglucosamines and polygalactosamines

Country Status (1)

Country Link
WO (2) WO2007001283A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2010552B1 (en) * 2006-04-07 2011-07-06 E.I. Du Pont De Nemours And Company Processes for chemical synthesis of lipochitooligosaccharides

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2640628A1 (en) * 1988-12-16 1990-06-22 Commissariat Energie Atomique beta -(1->6) Bonded oligosaccharides, in particular 2-acetamido-2-deoxy-glucoses or -galactoses and their preparation.
WO2003026677A1 (en) * 2001-09-26 2003-04-03 Primex Ehf. Pharmaceutical composition comprising chito-oligomers
WO2003070008A1 (en) * 2002-02-21 2003-08-28 Caldwell Bio Fermentation Canada Inc. Hydrolysed chitosan as antimicrobial coumpound and uses thereof
WO2003106471A1 (en) * 2002-06-12 2003-12-24 Alchemia Pty Ltd Combinatorial oligosaccharide synthesis

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4927826A (en) * 1987-07-10 1990-05-22 Hoffman-La Roche Inc. Cycloproylpropenamides useful as platelet activing factor (PAF) antagonists
US6541467B1 (en) * 2000-04-14 2003-04-01 Corvas International, Inc. Thrombin inhibitors having a lactam at P3

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2640628A1 (en) * 1988-12-16 1990-06-22 Commissariat Energie Atomique beta -(1->6) Bonded oligosaccharides, in particular 2-acetamido-2-deoxy-glucoses or -galactoses and their preparation.
WO2003026677A1 (en) * 2001-09-26 2003-04-03 Primex Ehf. Pharmaceutical composition comprising chito-oligomers
WO2003070008A1 (en) * 2002-02-21 2003-08-28 Caldwell Bio Fermentation Canada Inc. Hydrolysed chitosan as antimicrobial coumpound and uses thereof
WO2003106471A1 (en) * 2002-06-12 2003-12-24 Alchemia Pty Ltd Combinatorial oligosaccharide synthesis

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
ALY M R E ET AL: "Synthesis of chitotetraose and chitohexaose based on dimethylmaleoyl protection", CARBOHYDRATE RESEARCH, ELSEVIER SCIENTIFIC PUBLISHING COMPANY. AMSTERDAM, NL, vol. 331, no. 2, 22 March 2001 (2001-03-22), pages 129 - 142, XP004231171, ISSN: 0008-6215 *
ANDO, HIROMUNE ET AL: "Tag-Reporter Strategy for Facile Oligosaccharide Synthesis on Polymer Support", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 123(16), 3848-3849 CODEN: JACSAT; ISSN: 0002-7863, 2001, XP002430933 *
CHOWDHARY, MANJIT S. ET AL: "The assembly of oligosaccharides from "standardized intermediates": .beta.-(1 .fwdarw. 3)-linked oligomers of D-galactose", CARBOHYDRATE RESEARCH , 150, 173-85 CODEN: CRBRAT; ISSN: 0008-6215, 1986, XP002430931 *
FRIDMAN M. ET AL.: "One-Pot Synthesis of Glucosamine Oligosaccharides", ORGANIC LETTERS, vol. 4, no. 2, 2002, pages 281 - 283, XP002430934 *
HANSSON J. ET AL.: "Syntheses of Anomerically Phosphodiester-Linked Oligomers of the Repeating Units of the Haemophilus influenzae Types c and f Capsular Polysaccharides", JOURNAL OF ORGANIC CHEMISTRY, 2001, pages 6234 - 6243, XP002430935 *
HUANG X. ET AL.: "Iterative One-Pot Synthesis of Oligosaccharides", ANGEWANDTE CHEMIE INTERNATIONAL EDITION IN ENGLISH, vol. 43, 2004, pages 5221 - 5224, XP002430932, ISSN: 0570-0833 *
KANIE O ET AL: "ORTHOGONAL GLYCOSYLATION STRATEGY IN OLIGOSACCHARIDE SYNTHESIS", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 116, no. 26, 1994, pages 12073 - 12074, XP001093701, ISSN: 0002-7863 *
LICHTENTHALER, FRIEDER W. ET AL: "Directed and efficient syntheses of .beta.(1.fwdarw.4)-linked galacto-oligosaccharides", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY , (20), 3849-3869 CODEN: EJOCFK; ISSN: 1434-193X, 2001, XP002430930 *
YANG F ET AL: "A practical synthesis of a (1->6)-linked beta-d-glucosamine nonasaccharide", CARBOHYDRATE RESEARCH, ELSEVIER SCIENTIFIC PUBLISHING COMPANY. AMSTERDAM, NL, vol. 338, no. 6, 14 March 2003 (2003-03-14), pages 495 - 502, XP004415948, ISSN: 0008-6215 *

Also Published As

Publication number Publication date
WO2007001282A2 (en) 2007-01-04
WO2007001283A3 (en) 2007-08-30
WO2007001283A2 (en) 2007-01-04

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