Understanding and Controlling Glycosylation Reactions

Project Information

GLYCONTROL

Grant agreement ID: 726072

DOI 10.3030/726072

Project closed

EC signature date 20 February 2017

Start date 1 May 2017

End date 31 October 2022

Funded under

• EXCELLENT SCIENCE - European Research Council (ERC)

Total cost € 2 000 000,00

EU contribution € 2 000 000,00

Coordinated by

UNIVERSITEIT LEIDEN
Netherlands

Publications

Peer reviewed articles (20)

Reactivity-Stereoselectivity Mapping for the Assembly of Mycobacterium Marinum Lipooligosaccharides

Author(s): Thomas Hansen; Tim P Ofman; Joey G C Vlaming; Ivan A. Gagarinov; Jessey van Beek; Tessa A Goté; Jacoba M Tichem; Gijs Ruijgrok; Herman S. Overkleeft; Dmitri V. Filippov; Gijsbert A. van der Marel; Jeroen D. C. Codée
Published in: Angewandte Chemie, Issue 4 January 2020,133, 2, 2020, Page(s) 950-958, ISSN 0044-8249
Publisher: John Wiley & Sons, Ltd
DOI: 10.1002/anie.202010280

Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions

Author(s): Hansen T., Elferink H., Hengst J.M.A. van, Houthuijs K.J., Remmerswaal W.A., Kromm A., Berden G., Vorm S. van der, Rijs A.M., Overkleeft H.S., Filippov D.V., Rutjes F.P.J.T., Marel G.A. van der, Martens J., Oomens J., Codée J.D.C., Boltje T.J.
Published in: Nature Communications, Issue 11, 2664, 29 May 2020, 2020, ISSN 2041-1723
Publisher: Nature Publishing Group
DOI: 10.1038/s41467-020-16362-x

Structural and biochemical characterization of the exopolysaccharide deacetylase Agd3 required for Aspergillus fumigatus biofilm formation

Author(s): Bamford N.C., Mauff F. Le, Loon J.C. van, Ostapska H., Snarr B.D., Zhang Y., Kitova E.N., Klassen J.S., Codee J.D.C., Sheppard D.C., Howell P.L.
Published in: Nature Communications, Issue 11, 2450 15 May 2020, 2022, ISSN 2041-1723
Publisher: Nature Publishing Group
DOI: 10.1038/s41467-020-16144-5

Reagent controlled stereoselective synthesis of teichoic acid α-(1,2)-glucans

Author(s): Liming Wang; Francesca Berni; Jacopo Enotarpi; Hermen S. Overkleeft; Gijs A. van der Marel; Jeroen D. C. Codée
Published in: Organic & Biomolecular Chemistry, Issue 18, 27 February 2020, 2020, Page(s) 2038-2050, ISSN 1477-0520
Publisher: Royal Society of Chemistry
DOI: 10.1039/d0ob00240b

Halogen atom participation in guiding the stereochemical outcomes of acetal substitution reactions

Author(s): Demkiw, K.M.; Remmerswaal, W.A.; Hansen, T.; Marel, G.A. van der; Codee, J.D.C.; Woerpel, K.A.
Published in: Angewandte Chemie, Issue 16 september 2022, 134, 42, 2022, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202209401

Mapping the effect of configuration and protecting group pattern on glycosyl acceptor reactivity

Author(s): Jacob van Hengst, Rik Hellemons, Wouter A. Remmerswaal, Koen van de Vrande, Thomas Hansen, Stefan van der Vorm, Herman S. Overkleeft, Gijs van der marel and Jeroen D Codee
Published in: Chemical Science, 2023, ISSN 2041-6520
Publisher: Royal Society of Chemistry
DOI: 10.1039/d2sc06139b

An Orthogonally Protected Cyclitol for the Construction of Nigerose- and Dextran-Mimetic Cyclophellitols.

Author(s): Tim P Ofman; Florian Küllmer; Gijsbert A. van der Marel; Jeroen D. C. Codée; Herman S. Overkleeft
Published in: Organic Letters, Issue 23(24), November 30 , 2021, 2021, Page(s) 9516 - 9519, ISSN 1523-7060
Publisher: American Chemical Society
DOI: 10.1021/acs.orglett.1c03723

Reagent Controlled Stereoselective Synthesis of α-Glucans

Author(s): Liming Wang, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codée
Published in: Journal of the American Chemical Society, Issue 140/13, 2018, Page(s) 4632-4638, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.8b00669

Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity

Author(s): Stefan van der Vorm, Jacob M. A. van Hengst, Marloes Bakker, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codée
Published in: Angewandte Chemie International Edition, Issue 57/27, 2018, Page(s) 8240-8244, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201802899

Reagent Controlled Stereoselective Assembly of α-(1,3)-Glucans

Author(s): Liming Wang, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codée
Published in: European Journal of Organic Chemistry, Issue 2019/10, 2019, Page(s) 1994-2003, ISSN 1434-193X
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/ejoc.201800894

Defining the S N 1 Side of Glycosylation Reactions: Stereoselectivity of Glycopyranosyl Cations

Author(s): Thomas Hansen, Ludivine Lebedel, Wouter A. Remmerswaal, Stefan van der Vorm, Dennis P. A. Wander, Mark Somers, Herman S. Overkleeft, Dmitri V. Filippov, Jérôme Désiré, Agnès Mingot, Yves Bleriot, Gijsbert A. van der Marel, Sebastien Thibaudeau, Jeroen D. C. Codée
Published in: ACS Central Science, 2019, ISSN 2374-7943
Publisher: ACS
DOI: 10.1021/acscentsci.9b00042

Ega3 from the fungal pathogen Aspergillus fumigatus is an endo-α-1,4-galactosaminidase that disrupts microbial biofilms

Author(s): Natalie C. Bamford, François Le Mauff, Adithya S. Subramanian, Patrick Yip, Claudia Millán, Yongzhen Zhang, Caitlin Zacharias, Adam Forman, Mark Nitz, Jeroen D. C. Codée, Isabel Usón, Donald C. Sheppard, P. Lynne Howell
Published in: Journal of Biological Chemistry, Issue 294/37, 2019, Page(s) 13833-13849, ISSN 0021-9258
Publisher: American Society for Biochemistry and Molecular Biology Inc.
DOI: 10.1074/jbc.ra119.009910

Acceptor reactivity in glycosylation reactions

Author(s): Stefan van der Vorm, Thomas Hansen, Jacob M. A. van Hengst, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codée
Published in: Chemical Society Reviews, Issue 48/17, 2019, Page(s) 4688-4706, ISSN 0306-0012
Publisher: Royal Society of Chemistry
DOI: 10.1039/c8cs00369f

Molecular mechanism of Aspergillus fumigatus biofilm disruption by fungal and bacterial glycoside hydrolases

Author(s): François Le Mauff, Natalie C. Bamford, Noor Alnabelseya, Yongzhen Zhang, Perrin Baker, Howard Robinson, Jeroen D. C. Codée, P. Lynne Howell, Donald C. Sheppard
Published in: Journal of Biological Chemistry, Issue 294/28, 2019, Page(s) 10760-10772, ISSN 0021-9258
Publisher: American Society for Biochemistry and Molecular Biology Inc.
DOI: 10.1074/jbc.ra119.008511

Cover Picture: Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity (Angew. Chem. Int. Ed. 27/2018)

Author(s): Stefan van der Vorm, Jacob M. A. van Hengst, Marloes Bakker, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codée
Published in: Angewandte Chemie International Edition, Issue 57/27, 2018, Page(s) 7905-7905, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201804576

Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides

Author(s): Liming Wang, Yongzhen Zhang, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codée
Published in: The Journal of Organic Chemistry, 2020, ISSN 0022-3263
Publisher: American Chemical Society
DOI: 10.1021/acs.joc.0c00703

Assembly of a Library of Pel-Oligosaccharides Featuring α-Glucosamine and α-Galactosamine Linkages

Author(s): Yongzhen Zhang; Liming Wang; Liming Wang; Herman S. Overkleeft; Gijsbert A. van der Marel; Jeroen D. C. Codée
Published in: Frontiers in Chemistry, Issue 26 January 2022, 10:842238, 2022, ISSN 2296-2646
Publisher: Frontiers
DOI: 10.3389/fchem.2022.842238

Synthesis and antibody binding studies of schistosome-derived oligo-α-(1-2)-l-fucosides

Author(s): Michael R. Harvey; Fabrizio Chiodo; Fabrizio Chiodo; Wouter Noest; Cornelis H. Hokke; Gijsbert A. van der Marel; Jeroen D. C. Codée
Published in: Molecules, Issue 26 (8), 2246, 13 April 2021, 2021, ISSN 1420-3049
Publisher: Multidisciplinary Digital Publishing Institute (MDPI)
DOI: 10.3390/molecules26082246

Synthesis and Structural Analysis of Aspergillus fumigatus Galactosaminogalactans Featuring α-Galactose, α-Galactosamine and α-N-Acetyl Galactosamine Linkages

Author(s): Yongzhen Zhang; Marcos Gómez-Redondo; Gonzalo Jiménez-Osés; Ana Ardá; Herman S. Overkleeft; Gijsbert A. van der Marel; Jesús Jiménez-Barbero; Jeroen D. C. Codée
Published in: Angewandte Chemie, Issue 132, 28 April 2020, 2020, Page(s) 12746-12750, ISSN 0044-8249
Publisher: John Wiley & Sons Ltd
DOI: 10.1002/ange.202003951

How Lewis Acids Catalyze Ring-Openings of Cyclohexene Oxide

Author(s): Hansen, T.; Vermeeren, P.; Yoshisada, R.; Filippov, D.V.; Marel, G.A. van der; Codee, J.D.C.; Hamlin, T.A.
Published in: The journal of Organic Chemistry, Issue 86,4, 4 February 2021, 2021, Page(s) 3565-3573, ISSN 0022-3263
Publisher: American Chemical Society
DOI: 10.1021/acs.joc.0c02955