Jean-Luc G. MONTCHAMP
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FUNDING: we gratefully acknowledge the following for the financial support of our research. NSF |
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Our group's research interests are in the areas of organophosphorus chemistry, and bioorganic/medicinal chemistry. The core of our program in chemical biology focuses on the mechanism-based design, synthesis and evaluation of biologically active molecules such as enzyme inhibitors, and the development of novel antisense oligonucleotides with emphasis on the application of automated synthesis and combinatorial techniques whenever possible. Unnatural compounds are synthesized to probe various biological processes. Applications of this research range from the elucidation of enzyme mechanisms to the preparation of molecules with potential medicinal use (anticancer, antiparasite, immuno suppressant, antisense, GABA analogues). One such medicinally oriented goal is the preparation and evaluation of new hydrolytically stable antisense oligonucleotides for sequence specific complexation to RNA and DNA targets. Finally, current investigations aiming at the modulation of GABA receptors with phosphinic analogues are relevant to the treatment of various central nervous system (CNS) disorders. A collaborative project with Professor Coffer has also been initiated to prepare the recognition component of biocompatible calcified nanoporous silicon sensor arrays. Our
second research interest concerns organophosphorus chemistry and is driven
by two main objectives: firstly, the development of P-chiral ligands to
be ultimately used in catalytic asymmetric transformations, including
transition metal-catalyzed reactions, and secondly, the building of a
methodology based on phosphorus compounds for organic synthesis as well
as for the preparation of compounds possessing potential biological activity. PUBLICATIONS AIBN-initiated Radical Reactions of Ethyl Phosphinate Antczak, M. I.; Montchamp, J.-L. Synthesis 2006, In press. Advances in the Synthesis of H-Phosphinic Acids and Esters Montchamp, J.-L. Specialty Chemicals Magazine 2006, 26, 44. "Direct
Monoalkylation of Alkyl Phosphinates to Access H-Phosphinic Acid Esters Radical
Reaction of Sodium Hypophosphite with Terminal Alkynes: Synthesis of 1,1-bis-H-Phosphinates Palladium-Catalyzed
Phosphorus-Carbon Bond Formation: Cross-Coupling Reactions of Alkyl Phosphinates
with Aryl, Heteroaryl, Alkenyl, Benzylic, and Allylic Halides and Triflates "Recent
Advances in Phosphorus-Carbon Bond Formation: Synthesis of H-Phosphinic
Acid Derivatives from Hypophosphorous Compounds", Montchamp, J.-L.
J. Organomet. Chem., 2005, 690, 2388
"Environmentally Benign Synthesis of H-Phosphinic Acids Using a Water-Tolerant,
Recyclable Polymer-Supported Catalyst", Deprèle, S.; Montchamp,
J.-L. Org. Lett. 2004, 6, 3805.
"Direct Synthesis of H-Aryl and H-Heteroarylphosphinic Esters via
Palladium-Catalyzed Cross-Coupling of Alkylphosphinates", Huang,
Z.; Bravo-Altamirano, K.; Montchamp, J.-L., Comptes Rendus Chimie
2004, 7/8-9, 763 (special issue "Main-Group Compounds
in Catalysis")
"Routes to Calcified Porous Silicon: Implications for Drug Delivery
and Biosensing", Coffer, J. L.; Montchamp, J.-L.; Aimone, J. B.;
Weis, R. P. Physica Status Solidi (a) 2003, 197,
336.
"Calcified Nanostructured Silicon Wafer Surfaces for Biosensing:
Effects of Surface Modification on Bioactivity", Weis, R. P.; Montchamp,
J.-L.; Coffer, J. L.; Desai, T. A.; Atthia, D. G. Disease Markers
2002, 18, 159.
"Palladium-Catalyzed Hydrophosphinylation of Alkenes and Alkynes",
Deprèle, S.; Montchamp, J.-L. J. Am. Chem. Soc. 2002,
124, 9386.
"Palladium-Catalyzed Cross-Coupling Reaction of Anilinium Hypophosphite
With Alkenyl Bromides and Triflates: Application to the Synthesis of GABA
Analogs", Dumond, Y. R.; Montchamp, J.-L. J. Organomet. Chem.
2002, 653, 252.
"A Novel and Convenient Preparation of Hypophosphite Esters",
Deprèle, S.; Montchamp, J.-L. J. Organomet. Chem. 2002,
643-644, 154.
"Triethylborane-Initiated Room Temperature Radical Addition of Hypophosphites
to Olefins: Synthesis of Monosubstituted Phosphinic Acids and Esters",
Deprèle, S.; Montchamp, J.-L. J. Org. Chem. 2001,
66, 6745.
"Synthesis of Monosubstituted Phosphinic Acids: Palladium-Catalyzed
Cross-Coupling Reactions of Anilinium Hypophosphite", Montchamp,
J.-L.; Dumond, Y. R. J. Am. Chem. Soc. 2001, 123,
510.
"Orthosilicate-Mediated Esterification of Monosubstituted Phosphinic
Acids", Dumond, Y. R.; Baker, R. L.; Montchamp, J.-L. Org. Lett.
2000, 2, 3341.
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© copyright Jean-Luc Montchamp