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UID:69d98c02a4f04
DTSTAMP:20260410T194714
DTSTART:20190125T110000
SEQUENCE:0
TRANSP:OPAQUE
DTEND:20190125T110000
URL:https://murmitoyen.com/events/vanille/udem/detail/856453-seminaire-etud
 iant-du-candidat-ryan-simard-professeur-guindon
LOCATION:Pavillon Roger Gaudry – Université de Montréal\, Montréal\, Q
 C\, Canada
SUMMARY:Séminaire étudiant du candidat Ryan Simard (Professeur Guindon)
DESCRIPTION:‘‘ Synthesis of trans-Bicyclo[4.4.0]Galactopyranosides for 
 the Design of Sialyl LewisX Glycomimetics ’’
\nEndroit : Pavillon Roge
 r-Gaudry\, salle G-415  à 11 h 00
\nCette conférence sera prononcée 
 par Monsieur Ryan Simard\, candidat au doctorat\, étudiant du Professeur 
 Yvan Guindon\, au département de chimie\, de l'Université de Montréal.

 \nRÉSUMÉ: The development of viable therapeutics mimicking sialyl LewisX
  (sLeX)\, the tetrasaccharide epitope responsible for binding to selectins
  is an important area of research and development. Selectins (E- and P-) a
 re a family of cell adhesion molecules that mediate the capture and slow r
 olling of circulating leukocytes during the early stages of inflammation. 
 Excessive recruitment of leukocytes is implicated in both acute and chroni
 c pathologies of inflammatory diseases.
\nEffective P-selectin antagonists
 \, recently developed by the Guindon laboratory\, were synthesized by repl
 acing the GlucNAc saccharide with an acyclic tartrate-based tether. The mo
 lecular plasticity granted by this tether may synergize with further preor
 ganization of distal pharmacophores. Of the four carbohydrates\, the Neu5A
 c exhibits the most flexibility\, and is commonly simplified with acyclic 
 derivatives. In this project we propose\, based on the spatial orientation
  of bound sLeX\, that implementation of an annulated trans-bicyclo[4.4.0]g
 alactopyranose architecture bearing an axial carboxylic acid would mimic t
 he active conformation of the Neu5Ac-Gal linkage. These synthetically chal
 lenging scaffolds were initially constructed via elaboration of a galactos
 ide moiety bearing an alkyne handle. The key element in this synthetic rou
 te is a stereoselective intramolecular cyclization\, the nature of which i
 s being studied both experimentally and computationally and is proposed to
  follow Curtin-Hammett kinetics. A second\, divergent synthetic pathway fe
 aturing an orthogonal glycosylation strategy to rapidly access novel carbo
 xylic acid bioisosteres is currently being investigated. The biological ac
 tivity of these second-generation selectin antagonists is being assessed t
 hrough in vitro cell-adhesion assays and in vivo peritoneal lavage experim
 ents. Initial results show improved activity as compared to the native lig
 and (sLeX).
\n 
\n            Informations supplémentaires sur le 
 Professeur Guindon
\n            Annonce PDF du séminaire
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