WO2013013244A3 - Chemoenzymatic synthesis of heparin and haparan sulfate analogs - Google Patents

Chemoenzymatic synthesis of heparin and haparan sulfate analogs Download PDF

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Publication number
WO2013013244A3
WO2013013244A3 PCT/US2012/047875 US2012047875W WO2013013244A3 WO 2013013244 A3 WO2013013244 A3 WO 2013013244A3 US 2012047875 W US2012047875 W US 2012047875W WO 2013013244 A3 WO2013013244 A3 WO 2013013244A3
Authority
WO
WIPO (PCT)
Prior art keywords
heparin
chemoenzymatic synthesis
haparan
sulfate analogs
analogs
Prior art date
Application number
PCT/US2012/047875
Other languages
French (fr)
Other versions
WO2013013244A2 (en
Inventor
Xi Chen
Hai Yu
Yanhong Li
Yi Chen
Jingyao QU
Musleh M. MUTHANA
Original Assignee
The Regents Of The University Of California
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 The Regents Of The University Of California filed Critical The Regents Of The University Of California
Publication of WO2013013244A2 publication Critical patent/WO2013013244A2/en
Publication of WO2013013244A3 publication Critical patent/WO2013013244A3/en
Priority to US14/160,451 priority Critical patent/US9290530B2/en
Priority to US15/017,365 priority patent/US10160986B2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • 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
    • C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof
    • 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
    • C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
    • 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
    • C12P19/12—Disaccharides
    • 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
    • C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
    • 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
    • C12P19/28—N-glycosides
    • C12P19/30—Nucleotides
    • C12P19/305—Pyrimidine nucleotides
    • 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
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Saccharide Compounds (AREA)
  • Enzymes And Modification Thereof (AREA)

Abstract

The present invention provides a one-pot, multi-enzyme method for preparing UDP-sugars from simple sugar starting materials. The invention also provides a one-pot, multi-enzyme method for preparing oligosaccharides from simple sugar starting materials.
PCT/US2012/047875 2011-07-21 2012-07-23 Chemoenzymatic synthesis of heparin and haparan sulfate analogs WO2013013244A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US14/160,451 US9290530B2 (en) 2011-07-21 2014-01-21 Chemoenzymatic synthesis of heparin and heparan sulfate analogs
US15/017,365 US10160986B2 (en) 2011-07-21 2016-02-05 Chemoenzymatic synthesis of heparin and heparan sulfate analogs

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161510125P 2011-07-21 2011-07-21
US61/510,125 2011-07-21

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US14/160,451 Continuation-In-Part US9290530B2 (en) 2011-07-21 2014-01-21 Chemoenzymatic synthesis of heparin and heparan sulfate analogs

Publications (2)

Publication Number Publication Date
WO2013013244A2 WO2013013244A2 (en) 2013-01-24
WO2013013244A3 true WO2013013244A3 (en) 2013-07-11

Family

ID=47558757

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2012/047875 WO2013013244A2 (en) 2011-07-21 2012-07-23 Chemoenzymatic synthesis of heparin and haparan sulfate analogs

Country Status (1)

Country Link
WO (1) WO2013013244A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3097080A1 (en) 2014-01-24 2016-11-30 SynAffix B.V. Process for the cycloaddition of a halogenated 1,3-dipole compound with a (hetero)cycloalkyne
EP3925951A1 (en) 2014-01-24 2021-12-22 SynAffix B.V. Process for the cycloaddition of a(hetero)aryl 1,3-dipole compound with a (hetero)cycloalkyne
WO2015112013A1 (en) * 2014-01-24 2015-07-30 Synaffix B.V. Process for the attachment of a galnac moiety comprising a (hetero)aryl group to a glcnac moiety, and product obtained thereby
CN105886571B (en) * 2016-04-22 2019-08-06 山东大学 The synthetic method of Antigen of human blood group P1 pentasaccharides
CN108409815B (en) * 2018-03-26 2021-08-03 郑州安图生物工程股份有限公司 Indole glycoside substrate, preparation method and application in aerobic flora vaginitis detection
CN109321508B (en) * 2018-10-12 2022-12-27 北京化工大学 Genetic engineering bacterium for producing hepanosan and application thereof
US11441131B2 (en) 2019-06-21 2022-09-13 The Regents Of The University Of California Heparosan synthases and use thereof for saccharide synthesis

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5824472A (en) * 1986-03-24 1998-10-20 Monsanto Company Process for the synthesis of sugar nucleotides using recombinant-DNA methods
US6040158A (en) * 1996-09-11 2000-03-21 Yamasa Corporation Process for preparing sugar nucleotide
WO2006043525A1 (en) * 2004-10-21 2006-04-27 Yamasa Coporation Method of producing uridine 5’-diphospho-n-acetylgalactosamine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5824472A (en) * 1986-03-24 1998-10-20 Monsanto Company Process for the synthesis of sugar nucleotides using recombinant-DNA methods
US6040158A (en) * 1996-09-11 2000-03-21 Yamasa Corporation Process for preparing sugar nucleotide
WO2006043525A1 (en) * 2004-10-21 2006-04-27 Yamasa Coporation Method of producing uridine 5’-diphospho-n-acetylgalactosamine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KLECZKOWSKI, L. A. ET AL.: "UDP-sugar pyrophosphorylase: A new old mechanism for sugar activation.", PLANT PHYSIOLOGY, vol. 156, 28 March 2011 (2011-03-28), pages 3 - 10, XP055078335 *

Also Published As

Publication number Publication date
WO2013013244A2 (en) 2013-01-24

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