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GLYCONTROL SIGNED

Understanding and Controlling Glycosylation Reactions

Total Cost €

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EC-Contrib. €

0

Partnership

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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.

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

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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