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GLYCONTROL SIGNED

Understanding and Controlling Glycosylation Reactions

Total Cost €

0

EC-Contrib. €

0

Partnership

0

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 GLYCONTROL project word cloud

Explore the words cloud of the GLYCONTROL project. It provides you a very rough idea of what is the project "GLYCONTROL" about.

species    carbohydrate    oligosaccharides    super    triflates    glycosidic    generate    sn1    syntheses    oligosaccharide    operates    quantified    procedure    united    donor    exactly    media    intermediates    glycosyl    productivity    nmr    charts    employed    spanning    acid    featuring    cis    gap    predict    structural    competition    sn2    compiled    blocks    kinetic    family    limited    variation    automated    computational    linkages    nucleophile    central    glycoside    window    libraries    glycosylations    activated    nucleophilicity    mechanisms    relative    building    place    made    matched    outcome    glycosylation    probed    reactivity    impossible    covalent    activation    spectroscopy    tailor    takes    reactions    oxocarbenium    fundamental    ion    bridging    form    fleeting    multiple    acceptor    stereoselectivity    acceptors    solid    experiments    cations    leads    donors    reactive    stable    systematically    modulators    innovative    broad    predictable    chemistry    methodology    reaction    provides    understand    continuum    anomeric   

Project "GLYCONTROL" data sheet

The following table provides information about the project.

Coordinator
UNIVERSITEIT LEIDEN 

Organization address
address: RAPENBURG 70
city: LEIDEN
postcode: 2311 EZ
website: www.universiteitleiden.nl

contact info
title: n.a.
name: n.a.
surname: n.a.
function: n.a.
email: n.a.
telephone: n.a.
fax: n.a.

 Coordinator Country Netherlands [NL]
 Total cost 2˙000˙000 €
 EC max contribution 2˙000˙000 € (100%)
 Programme 1. H2020-EU.1.1. (EXCELLENT SCIENCE - European Research Council (ERC))
 Code Call ERC-2016-COG
 Funding Scheme ERC-COG
 Starting year 2017
 Duration (year-month-day) from 2017-05-01   to  2022-04-30

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    UNIVERSITEIT LEIDEN NL (LEIDEN) coordinator 2˙000˙000.00

Map

 Project objective

This proposal aims to understand and control glycosylation reactions. In a glycosylation reaction a “donor” glycoside and an “acceptor” (the nucleophile) are united to form an oligosaccharide. Although it is the central reaction in carbohydrate chemistry, our understanding of this reaction, in terms of stereoselectivity and productivity is still limited. The structural variation in the building blocks leads to a complex continuum of SN2-SN1 mechanisms that operates and it is currently impossible to predict where in the continuum the reaction exactly takes place. This proposal provides fundamental insight into the outcome of glycosylations by studying both the activated donor glycoside and the acceptor nucleophile. Activation of a donor glycoside leads to different reactive intermediates, covalent anomeric species (most often triflates) and oxocarbenium ion-like species. The relative reactivity of these species is quantified to generate novel reactivity charts. The covalent species are studied by innovative competition experiments, kinetic studies and NMR spectroscopy. The (fleeting) oxocarbenium ion-like intermediates are probed by a computational approach and by “super-acid NMR” studies in which stable glycosyl cations are generated and studied in super-acid media. The reactivity of glycosyl acceptors is systematically studied in a set of SN2 or SN1-type glycosylations. Using kinetic studies and competition reactions charts of acceptor nucleophilicity are compiled. The reactivity of the donors and acceptors is matched using a family of tailor made “reactivity modulators”, spanning a broad reactivity window bridging the reactivity gap between the building blocks leading to predictable glycosylations. The developed methodology is employed in automated solid phase syntheses of libraries of oligosaccharides featuring multiple cis-glycosidic linkages. The proposal is a major step forward in the development of a general glycosylation procedure.

 Publications

year authors and title journal last update
List of publications.
2019 Liming Wang, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codée
Reagent Controlled Stereoselective Assembly of α-(1,3)-Glucans
published pages: 1994-2003, ISSN: 1434-193X, DOI: 10.1002/ejoc.201800894
European Journal of Organic Chemistry 2019/10 2020-01-28
2018 Stefan van der Vorm, Jacob M. A. van Hengst, Marloes Bakker, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codée
Cover Picture: Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity (Angew. Chem. Int. Ed. 27/2018)
published pages: 7905-7905, ISSN: 1433-7851, DOI: 10.1002/anie.201804576
Angewandte Chemie International Edition 57/27 2020-01-28
2019 Stefan van der Vorm, Thomas Hansen, Jacob M. A. van Hengst, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codée
Acceptor reactivity in glycosylation reactions
published pages: 4688-4706, ISSN: 0306-0012, DOI: 10.1039/c8cs00369f
Chemical Society Reviews 48/17 2020-01-28
2018 Stefan van der Vorm, Jacob M. A. van Hengst, Marloes Bakker, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codée
Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity
published pages: 8240-8244, ISSN: 1433-7851, DOI: 10.1002/anie.201802899
Angewandte Chemie International Edition 57/27 2019-03-13
2018 Liming Wang, Herman S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codée
Reagent Controlled Stereoselective Synthesis of α-Glucans
published pages: 4632-4638, ISSN: 0002-7863, DOI: 10.1021/jacs.8b00669
Journal of the American Chemical Society 140/13 2019-03-13

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