Institut de Chimie Moléculaire et des Matériaux d'Orsay

Laboratoire de Synthèse Organique et Méthodologie - LSOM

The Laboratory welcomes students from DUT, BTS, M1 and M2 and engineering students.

Financal support

For 3rd year students in engineering schools where the school is accredited by the CNRS an application for funding is possible with this organization.

 

ERASMUS Students

ERASMUS foreign students wishing to intern in the Laboratory should contact the international relations department at their university which will connect with international service Realtions University Paris-Sud (click here ).

 

Available topics

  • Synthesis of Heterocyclic acids aminophosphonic interest biological antitumor Cyclopeptides. (A. Fadel, N. Rabasso)

The aim of this project is to develop new methodologies for synthesis of heterocyclic amino acids, enantiomerically pure, based on the work already done at the Laboratory. These non-natural amino acids are incorporated in cyclopeptides potentially cancer. Learn more...

 

The flaws inherent in α-peptides, such as insufficient stability of secondary structures or degradation by proteolytic enzymes, can be circumvented by the use of oligomers of β-amino acids. In solution, the β-peptides form stable secondary structures, like helices, sheets and elbows, posing a significant therapeutic potential. Severe conformational constraints in the β-amino cyclobutane make these molecules particularly interesting to study. In this context, we recently established a synthetic route short and efficient skeleton of cis-β-amino cyclobutane 1 via a strategy of photocycloaddition [2 +2] (Aitken et al. Tetrahedron Lett. 2002, 43, 6177; Tetrahedron Lett. 2004, 45, 7095).
In parallel with the development of peptides incorporating this reason, we consider the "aza-analogue, compound 2. The synthesis and study of the behavior of compounds that l 'can be called aza-β-amino acids is an area almost completely blank (only exception: Seebach et al. Helv. Chim. Acta 2003, 86, 4152).
The objective of this course is to synthesize the compound 2 by a process of photocycloaddition [2 +2] after the commercial aza-uracil. The aza-β-amino acid 2 is then incorporated in a simple peptide, which will be analyzed by NMR to determine the conformational preferences.


 

The organosilicon compounds are studied for their biological properties more frequently. Indeed, the silicon atom, which lies just below carbon in the periodic table has similarities with it (forming tetrasubstituted compounds) but also differences (possible formation of compounds penta-and hexasubstitués). The sila-substitution of one carbon atoms of a biologically active compound is a method to access new compounds with pharmacokinetic and pharmacodynamic properties different from those of the analogous carbon. We propose to prepare new compounds silica replacement of one atom of carbon quaternary compounds with biological properties. Indeed, the Si-H bond is much more reactive than the CH bond and the sila-substitution at a CH2 or CH would a priori much less stable compounds in biological media.

The profadol 1b the picénadol 2b and 3b are decahydroisoquinoléines compounds with similar activities of morphine. The sila-substituted quaternary carbon would lead to new compounds 1a, 2a and 3a with a priori similar activities but with potentially interesting characteristics. In particular, changes in metabolic pathways may help avoid unwanted side effects. In the case of compounds with piperidine, type effects Parkinson's disease are attributed to the formation in vivo by loss of pyridinium substituent quaternary carbon and flavoring. The formation of a double bond to one silicon atom is more difficult than on a carbon, such flavor is slower or impossible with silapipéridines.Learn more...