Level of study
BAC +4
ECTS
2 credits
Component
Faculty of Science
Description
Fluorinated biomolecules. Current developments of fluorinated molecules. Methods of fluorination: nucleophilic or electrophilic mono-fluorination, introduction of difluoromethyl or trifluoromethyl groups. Contribution of fluorine atoms in the activity of these compounds. Examples of syntheses of fluorinated compounds used as antitumor agents, antiviral agents, antidepressants, anxiolytics, anti-inflammatories...
Phosphorus biomolecules. Structure, nomenclature, reactivity, structural analysis and applications.
Some synthetic routes of compounds of each of the treated families will be discussed, highlighting, if necessary, non-conventional activation methods. Biomedical applications will be targeted, as well as other applications in agrochemistry, optoelectronics, nanomaterials, ...
Hourly volumes* :
CM : 15 h (7,5h Fluorinated biomolecules and 7,5h Phosphorated biomolecules)
TD : 5 h
Objectives
Expertise in the synthesis of fluorinated biomolecules
Phosphorus chemistry skills
Necessary pre-requisites
L3 Organic Chemistry
Knowledge control
Final written exam of 2 hours:
- Authorized documents: no
- Internet allowed : no
Syllabus
Support(s) available on ENT (Moodle): Course documents, TD documents, exam annals and reference publications.
Course
Fluorinated biomolecules
- Current developments in fluorinated molecules. 1,5 h
- Interest/ Contribution of the fluorine atom(s) on a biomolecule
- Nucleophilic and electrophilic mono-fluorination methods. 3h
- Aminosulfurane and derivatives, N-fluorosulfinimide and derivatives
- Introduction of trifluoromethyl or difluoromethyl groups. 1,5 h
- Ruppert-Prakash reagent and derivatives
- Synthesis of fluorinated biomolecules (antitumor drugs, antidepressants, ...). 1,5 h
Phosphorus Biomolecules
- The element phosphorus and phosphorus molecules. 2 x 1.5 h
- Structure and nomenclature of functional groups of P(III) and P(V) derivatives
- Structure and biological functions of phosphorus-containing biomolecules: nucleotides, nucleic acids, phospholipids, etc.
- Phosphorus NMR: applications to physicochemical characterization and reaction monitoring
- The major reactions involving phosphines (Appel, Mitsunobu, Staudinger, aza-Wittig), phosphites (Michaelis-Arbuzov), phosphonium ylides (Wittig), phosphine oxides (Wittig-Horner), phosphonates (Horner-Wadsworth-Emmons) and H-phosphonates (Michaelis-Becker, Atherton-Todd)
- 2. Organophosphorus compounds: synthesis and applications in the medical field 3 x 1.5 h
- Nucleotides, analogues and nucleotide prodrugs (anticancer, antiviral, diagnostic use)
- Bisphosphonates (anti-osteoporotic, anticancer, theranostic agents)
- Phosphorus-containing amino acids
- Phosphate prodrugs of steroids (antibiotics, anti-inflammatories, immunosuppressants)
- Oxazaphosphorines and phosphorotriamidates (DNA alkylating agents, anticancer agents)
TD (5 H) for both parts of the course: Individual work, exercises to prepare before and during the session.
Additional information
Teaching team :
Christophe Mathé
Béatrice Roy
Jean-Pierre Uttaro
Administrative contact(s):
Secretariat Master Chemistry
https://master-chimie.edu.umontpellier.fr/