Study level
BAC +5
ECTS
2 credits
Component
Faculty of Science
Description
The following topics will be covered:
- General mechanism of glycosylation
- Glycosyl donor synthesis
- Glycosyl donor activation methods
- Stereoselective synthesis of some natural oligosaccharides
Hourly volumes* :
CM: 15
TD : 5
Objectives
The aim of this course is to apply the knowledge of glycochemistry acquired in L3 (HAC605C) to modern techniques for the synthesis of natural glycosides and oligosaccharides.
Necessary prerequisites
Organic chemistry, L3 level
Knowledge control
2-hour written final exam
- Authorized documents: no
- Non-graphic calculator allowed: yes
- Internet allowed: no
Syllabus
Courses (15 H): Materials available on ENT (Moodle): Course documents, TD documents, exam annals and reference publications.
- Glycosylation mechanism: (3H)
structure and conformation of intermediates and transition states
using a participating group
use of participating and non-participating solvents
effect of temperature
SN2methods
- Glycosyl donors: (6H)
halides
trichloroacetimidates
phosphites and phosphates
pentenyl glycosides
xanthates
thioglycosides
- Activation of glycosyl donors: (3H)
Lewis acids
alkylating agents
metal salts
radical cations
- Synthesis of natural oligosaccharides: (3H)
blood group determinants
tetrasaccharide sialyl-Lewis X
Tutorials (5 hours): Individual work, exercises to be prepared before and during the session.
Exercises on the chemical compatibility of glycosyl donors and acceptors during glycosylation. Exercises on activator selection. Exercises on stereochemical control of glycosidic couplings.
Further information
Administrative contact(s) :
Secretariat Master Chemistry
https://master-chimie.edu.umontpellier.fr/