Xavier Pannecoucke

Chiral dipeptide mimics possessing a fluoroolefin moiety: a relevant tool for conformational and medicinal studies

The replacement of the amide bond in a peptide backbone is a promising strategy in peptidomimetic drug research. Over the various amide bond surrogates, the fluoroolefin moiety has been successfully developed as an effective mimic. Today, fluorine-containing compounds account for a large proportion of new active molecules in life sciences. The synthesis of fluoroolefin peptide mimics is not a trivial task and innovative approaches often need to be addressed, in particular for the stereocontrol of the double bond configuration and the chiral centres adjacent to the fluoroalkene. These fluorinated peptidomimetics have been synthesised and evaluated as metabolically stable and/or conformationally constrained analogs of enzyme inhibitors, and as tools for probing the function, structure, and binding process of receptors.

Ruthenium‐Catalyzed Redox Isomerization of Trifluoromethylated Allylic Alcohols: Mechanistic Evidence for an Enantiospecific Pathway

Transfer news: A synthetic approach to chiral β-CF(3)-substituted saturated carbonyl compounds has been developed in which ruthenium complexes efficiently catalyze the redox isomerization of CF(3)-bearing allylic alcohols by an intramolecular suprafacial enantiospecific 1,3-hydrogen transfer (see scheme). This method was used for the enantioselective synthesis of (S)-CF(3)-citronellol.

Straightforward Preparation of Functionalized α‐CF2‐Galactosides through an Oxygen to Carbon Acyl Migration

A high number of O-glycoconjugates of therapeutic interest feature an a-galactose or 2-deoxy-2-acetamido-a-galactose unit in their structure, often serving as the link between the aglycon and the glycosidic parts. For example, this motif is found in tumor-associated antigens, antifreeze glycoproteins (AFGP) or in immunoregulative a-galactosylceramides. This last family of glycosphingolipids (agelasphins) exhibit strong in vivo activities against infectious diseases and tumor metastases, which were found to be related to their immunoregulative properties.

CCDC 872138: Experimental Crystal Structure Determination

Related Article: Guillaume Dutheuil, Camille Pierry, Emilie Villiers, Samuel Couve-Bonnaire and Xavier Pannecoucke|2013|New J.Chem.|37|1320|doi:10.1039/C2NJ40891K