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

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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