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GLYCONTROL SIGNED

Understanding and Controlling Glycosylation Reactions

Total Cost €

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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.

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

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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