WO2006003456A3 - Glycosylation of antibiotics - Google Patents

Glycosylation of antibiotics Download PDF

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Publication number
WO2006003456A3
WO2006003456A3 PCT/GB2005/002661 GB2005002661W WO2006003456A3 WO 2006003456 A3 WO2006003456 A3 WO 2006003456A3 GB 2005002661 W GB2005002661 W GB 2005002661W WO 2006003456 A3 WO2006003456 A3 WO 2006003456A3
Authority
WO
WIPO (PCT)
Prior art keywords
sugar
enzymes
demonstrated
enzyme
donor
Prior art date
Application number
PCT/GB2005/002661
Other languages
French (fr)
Other versions
WO2006003456A2 (en
Inventor
Benjamin Guy David
Harry John Gilbert
Original Assignee
Isis Innovation
Benjamin Guy David
Harry John Gilbert
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 GB0415264A external-priority patent/GB0415264D0/en
Priority claimed from GB0509941A external-priority patent/GB0509941D0/en
Application filed by Isis Innovation, Benjamin Guy David, Harry John Gilbert filed Critical Isis Innovation
Publication of WO2006003456A2 publication Critical patent/WO2006003456A2/en
Publication of WO2006003456A3 publication Critical patent/WO2006003456A3/en

Links

Classifications

    • 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
    • C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
    • C12P19/62—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin the hetero ring having eight or more ring members and only oxygen as ring hetero atoms, e.g. erythromycin, spiramycin, nystatin

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)

Abstract

It has been demonstrated that macrolide glycosyltransferase enzymes can be recombinantly expressed at high levels. It has also been demonstrated that that these enzymes are able to accept a range of planar, cyclic, hydrophobic molecules in the aglycone binding site such that they may be used to glycosylate a range of substrates. It has been further demonstrated that these enzymes display a plasticity in donor sugar recognition such that they may be utilitised in introducing novel sugar decorations into bioactive molecules. Accordingly, the invention provides a method of attaching a sugar to a substrate comprising contacing the sugar with a macrolide glycosyltransferase enzyme in the presence of a sugar donor. The invention also provides a method of recombinantly expressing a macrolide glycosyltransferase enzyme at a high level comprising expressing a polynucleotide encoding the enzyme in a bacterial host cell.
PCT/GB2005/002661 2004-07-07 2005-07-07 Glycosylation of antibiotics WO2006003456A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB0415264.1 2004-07-07
GB0415264A GB0415264D0 (en) 2004-07-07 2004-07-07 Glycosylation of antibiotics
GB0509941.1 2005-05-16
GB0509941A GB0509941D0 (en) 2005-05-16 2005-05-16 Glycosylation of antibiotics

Publications (2)

Publication Number Publication Date
WO2006003456A2 WO2006003456A2 (en) 2006-01-12
WO2006003456A3 true WO2006003456A3 (en) 2006-03-16

Family

ID=35056919

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2005/002661 WO2006003456A2 (en) 2004-07-07 2005-07-07 Glycosylation of antibiotics

Country Status (1)

Country Link
WO (1) WO2006003456A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006057303A1 (en) 2004-11-29 2006-06-01 National University Corporation Nagoya University Glycopeptide antibiotic monomer derivatives
TW200808818A (en) 2006-05-26 2008-02-16 Shionogi & Co Glycopeptide antibiotic derivatives
WO2009015268A2 (en) * 2007-07-24 2009-01-29 Wisconsin Alumni Research Foundation Engineered glycosyltransferases with expanded substrate specificity
CN101959900A (en) * 2007-12-26 2011-01-26 盐野义制药株式会社 Glycosylated glycopeptide antibiotic derivative
GB201017450D0 (en) 2010-10-15 2010-12-01 School Of Pharmacy The University Of London Glycosylation of aminocoumarins
WO2014185717A1 (en) * 2013-05-15 2014-11-20 한국생명공학연구원 Novel epothilone derivative and use thereof
EP3184514A1 (en) 2015-12-23 2017-06-28 Deutsches Krebsforschungszentrum Autophagy inhibitors
CN111138444B (en) * 2020-01-08 2022-05-03 山东大学 Epothilone B glucoside compounds and enzymatic preparation and application thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001079520A1 (en) * 2000-04-13 2001-10-25 Biotica Technology Limited Hybrid glycosylated products and their production and use

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001079520A1 (en) * 2000-04-13 2001-10-25 Biotica Technology Limited Hybrid glycosylated products and their production and use

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CUNDLIFFE E: "GLYCOSYLATION OF MACROLIDE ANTIBIOTICS IN EXTRACTS OF STREPTOMYCES-LIVIDANS", ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, vol. 36, no. 2, 1992, pages 348 - 352, XP008054118, ISSN: 0066-4804 *
QUIROS LUIS M ET AL: "Two glycosyltransferases and a glycosidase are involved in oleandomycin modification during its biosynthesis by Streptomyces antibioticus", MOLECULAR MICROBIOLOGY, vol. 28, no. 6, June 1998 (1998-06-01), pages 1177 - 1185, XP002349498, ISSN: 0950-382X *
YANG MIN ET AL: "High-throughput mass-spectrometry monitoring for multisubstrate enzymes: determining the kinetic parameters and catalytic activities of glycosyltransferases.", CHEMBIOCHEM : A EUROPEAN JOURNAL OF CHEMICAL BIOLOGY. FEB 2005, vol. 6, no. 2, February 2005 (2005-02-01), pages 346 - 357, XP002349499, ISSN: 1439-4227 *

Also Published As

Publication number Publication date
WO2006003456A2 (en) 2006-01-12

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