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SWEET-PI SIGNED

Aromatic stacking in Glycochemistry: can glycosidations be tamed?

Total Cost €

0

EC-Contrib. €

0

Partnership

0

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 SWEET-PI project word cloud

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requiring    conformational    glycosidic    detected    complexes    alternatively    aromatic    chemical    stabilize    never    recognition    progress    too    appropriate    ion    participation    extend    glycosyltransferases    idea    employed    despite    life    molecular    reactivity    elusive    invoked    hypothesis    inter    interestingly    motifs    employing    interactions    carbohydrate    pi    variety    enzymatic    carboxylates    stabilized    models    potentially    glycosidation    central    detection    catalysis    stacking    group    frequently    reaction    functional    systematic    outcome    glycosyl    bioorganic    donor    intermediates    cationic    stability    ionic    glycostructures    supramolecular    expansion    time    synthesis    species    ch    molecules    glycoscience    stereochemical    chemistry    intramolecular    transient    acceptor    play    course    electron    intermediate    reactive    contacts    glycosidases    groups    oxocarbenium    interaction    modulation    first    accepted    bond    nucleophilicity    density    revolves    fact   

Project "SWEET-PI" data sheet

The following table provides information about the project.

Coordinator
AGENCIA ESTATAL CONSEJO SUPERIOR DEINVESTIGACIONES CIENTIFICAS 

Organization address
address: CALLE SERRANO 117
city: MADRID
postcode: 28006
website: http://www.csic.es

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 Spain [ES]
 Total cost 172˙932 €
 EC max contribution 172˙932 € (100%)
 Programme 1. H2020-EU.1.3.2. (Nurturing excellence by means of cross-border and cross-sector mobility)
 Code Call H2020-MSCA-IF-2018
 Funding Scheme MSCA-IF-EF-RI
 Starting year 2020
 Duration (year-month-day) from 2020-01-01   to  2021-12-31

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    AGENCIA ESTATAL CONSEJO SUPERIOR DEINVESTIGACIONES CIENTIFICAS ES (MADRID) coordinator 172˙932.00

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 Project objective

Progress in chemical synthesis has provided access to a large variety of complex glycostructures, having a major impact in the expansion of Glycoscience. Central to carbohydrate chemistry is the glycosidation reaction, which involves the formation of a glycosidic bond between donor and acceptor molecules. It is commonly accepted that this process requires the formation of transient ionic species, whose stability, conformational properties and interactions determine to a large extend the reaction outcome. In principle, these elusive species are stabilized by means of inter- and intramolecular interactions, and in fact, this is a key feature for the activity of glycosidases and glycosyltransferases, typically requiring the participation of electron-rich functional groups, such as carboxylates. Interestingly, aromatic/carbohydrate interactions have too been detected and evaluated as supramolecular recognition motifs but, to the best of our knowledge, never at the reaction intermediate level, despite being frequently invoked to play a major role during enzymatic catalysis. Our hypothesis in this project revolves around the idea that stacking interactions involving electron-rich aromatic systems can be employed to stabilize the glycosyl oxocarbenium ion and to enhance the glycosyl acceptor reactivity; in the first case, these contacts might increase the life-time of the cationic intermediates, facilitating their detection and potentially allowing the modulation of the glycosidic donor in order to better control the stereochemical course of the reaction. Alternatively, CH/pi complexes involving the glycosyl acceptor could enhance the electron density of the reactive functional group, thus its nucleophilicity. This project aims to test both aspects of the carbohydrate/aromatic interaction employing a bioorganic approach based on the design, synthesis and systematic analysis of appropriate molecular models.

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