Total synthesis of sinapigladioside, an antifungal phenolic glycoside from Burkholderia gladioli

  • Master
  • Fall
  • With scholarship

Project description

Antifungal infections currently pose a serious threat to human health. Multi-resistant strains of fungi resistant to the four main classes of clinically used antifungal agents have started to appear in hospital settings. To ward off these often-fatal infections, it is requested to accelerate the preclinical development of antifungal agents having unprecedented mechanisms of action. Bacteria currently represent an unrivaled source for the discovery of antimicrobial agents. Accordingly, Gram-negative bacteria of the genus Burkholderia are highly prized by the scientific community for their ability to produce antimicrobial molecules with novel molecular structures. Recently, researchers have carried out the isolation and structural identification of a new antifungal molecule (i.e., sinapigladioside) from organic extracts of Burkholderia gladioli, a bacterium living in symbiosis with certain plants. Structurally, sinapigladioside is a glycoside containing a regioselectively methylated disaccharide section and a phenolic aglycone bearing an isothiocyanate function. The main objective of this research project is to carry out the total synthesis of sinapigladioside and its derivatives. The synthesized compounds will be evaluated in vitro for their antifungal and antibacterial properties in the laboratories of our collaborators (Pr Éric Déziel, INRS, and Pr Adnane Sellam, U. Laval).

Research fields

  • Organic synthesis
  • Carbohydrate chemistry
  • Natural product chemistry
  • Antifungals

Research advisor

Charles Gauthier, professor

Starting date

Fall 2020

Study program

Master’s degree in experimentals health sciences – pharmacology & toxicology curriculum (French description)

Financial support

INRS offers many scholarship programs. Every student-researcher benefits from a grant during their higher education studies. This project is partially funded by the Natural Sciences and Engineering Research Council of Canada (NSERC) through the Discovery Grants program. The student will receive a scholarship for the duration of their master’s studies (maximum 2 years). If their application is selected, the recruited student must agree to submit their academic file to the provincial (FRQNT) and federal (CRSNG) granting bodies as well as to the Foundation Armand-Frappier (FAF) for the annual graduate scholarship competitions.


The candidate must hold a BSc in chemistry (or an equivalent degree) and have maintained a cumulative average of at least 3.0/4.3 or the equivalent. The student must have experience in organic synthesis and 1D and 2D NMR analyses. An interest in the chemistry of carbohydrates and natural products would be an asset.


Institut national de la recherche scientifique
Armand Frappier Santé Biotechnologie Research Centre
531, boulevard des Prairies
Laval, Québec G3X 1S2

How to apply

Interested persons can submit their application to Charles Gauthier in a single PDF file by using the online form. The application must include:

  • Motivation letter (maximum 1 page) describing their research interests
  • Complete CV
  • All transcripts of most recente diploma
  • The name of two contact information who can provides references
Project Charles Gauthier - Total synthesis of sinapigladioside, an antifungal phenolic ...

Project title : Total synthesis of sinapigladioside, an antifungal phenolic glycoside from Burkholderia gladioli

Curriculum vitæ *
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Academic transcript *
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Motivation letter *
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Charles Gauthier
Phone: 450-687-5010 extension 8886