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

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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