Jean-Maurice Mallet
Centre national de la recherche scientifique
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Featured researches published by Jean-Maurice Mallet.
Journal of Carbohydrate Chemistry | 1999
Yongmin Zhang; Jacques Esnault; Jean-Maurice Mallet; Pierre Sinay
ABSTRACT A total synthesis of the β-methyl glycoside of lacto-N-fucopentaose III (1) is described. Phenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (4), a key intermediate prepared by condensation of 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide (2) and phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (3), was glycosylated with ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (5) to give the trisaccharide donor 6, which, on coupling with methyl 2,6-di-O-benzyl-β-D-galactopyranosyl-(1→4) 2,3,6-tri-O-benzyl-β-D-glucopyranoside (7), afforded the pentasaccharide 8. It was easily transformed into the target pentasaccharide 1 via hydrazinolysis, acetylation, O-deacetylation, and hydrogenolysis.
Journal of Chemical Biology | 2010
Laurence Dutot; Pascaline Lécorché; Fabienne Burlina; Rodrigue Marquant; Vanessa Point; Sandrine Sagan; Gérard Chassaing; Jean-Maurice Mallet; Solange Lavielle
Cell-penetrating peptides (CPPs), which are usually short basic peptides, are able to cross cell membranes and convey bioactive cargoes inside cells. CPPs have been widely used to deliver inside cells peptides, proteins, and oligonucleotides; however, their entry mechanisms still remain controversial. A major problem concerning CPPs remains their lack of selectivity to target a specific type of cell and/or an intracellular component. We have previously shown that myristoylation of one of these CPPs affected the intracellular distribution of the cargo. We report here on the synthesis of glycosylated analogs of the cell-penetrating peptide (R6/W3): Ac-RRWWRRWRR-NH2. One, two, or three galactose(s), with or without a spacer, were introduced into the sequence of this nonapeptide via a triazole link, the Huisgen reaction being achieved on a solid support. Four of these glycosylated CPPs were coupled via a disulfide bridge to the proapoptotic KLAK peptide, (KLAKLAKKLAKLAK), which alone does not enter into cells. The effect on cell viability and the uptake efficiency of different glycosylated conjugates were studied on CHO cells and were compared to those of the nonglycosylated conjugates: (R6/W3)S-S-KLAK and penetratinS-S-KLAK. We show that glycosylation significantly increases the cell viability of CHO cells compared to the nonglycosylated conjugates and concomitantly decreases the internalization of the KLAK cargo. These results suggest that glycosylation of CPP may be a key point in targeting specific cells.
Gastroenterology | 2006
Annie Standaert–Vitse; Thierry Jouault; Peggy Vandewalle; Céline Mille; Mimouna Seddik; Boualem Sendid; Jean-Maurice Mallet; Jean-Frédéric Colombel; Daniel Poulain
Organic Letters | 2007
Stéphane Gaillard; Aleksey Yakovlev; Camilla Luccardini; Martin Oheim; and Anne Feltz; Jean-Maurice Mallet
Archive | 2006
Jacques Esnault; Pierre Sinaÿ; Reynald Chevalier; Jean-Frédéric Colombel; Jean-Maurice Mallet; Boualem Sendid; Thierry Jouault; Daniel Poulain; Pierre-André Trinel
Synlett | 1998
El Djouhar Rekaï; Gilles Rubinstenn; Jean-Maurice Mallet; Pierre Sinay; Stephan N. Müller; Bernd Giese
Radicals in Organic Synthesis | 2008
Alan J. Pearce; Jean-Maurice Mallet; Pierre Sinaÿ
Heterocycles | 2000
Alan James Pearce; Jean-Maurice Mallet; Pierre Sinay
Archive | 2000
Jacques Esnault; Pierre Sinaÿ; Reynald Chevalier; Jean-Frédéric Colombel; Jean-Maurice Mallet; Boualem Sendid; Thierry Jouault; Daniel Poulain; Pierre-André Trinel
231st ECS Meeting (May 28 - June 1, 2017) | 2017
Martina Čížková; Laurent Cattiaux; Jean-Maurice Mallet; Eric Labbé; Olivier Buriez