Antoine Fadel
University of Paris-Sud
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Featured researches published by Antoine Fadel.
Tetrahedron-asymmetry | 2003
Molika Truong; Frédéric Lecornué; Antoine Fadel
Abstract An efficient and easy one-pot reaction from readily available racemic 2-substituted cyclobutanones gave, by means of asymmetric Strecker synthesis in the presence of an amine chiral auxiliary, two major aminonitriles with excellent diastereoselectivity. After separation, the major cis-aminonitriles were hydrolysed and hydrogenolysed to lead for the first time to pure non-racemic (+)-1-amino-2-isopropylcyclobutanecarboxylic acid (ACBC) and its antipode.
Journal of Biological Inorganic Chemistry | 2012
Lydie Brisson; Nadia El Bakkali-Taheri; Michel Giorgi; Antoine Fadel; József Kaizer; Marius Réglier; Thierry Tron; El Hassan Ajandouz; A. Jalila Simaan
Abstract1-Aminocyclopropane-1-carboxylic acid oxidase (ACCO) is a nonheme Fe(II)-containing enzyme that is related to the 2-oxoglutarate-dependent dioxygenase family. The binding of substrates/cofactors to tomato ACCO was investigated through kinetics, tryptophan fluorescence quenching, and modeling studies. α-Aminophosphonate analogs of the substrate (1-aminocyclopropane-1-carboxylic acid, ACC), 1-aminocyclopropane-1-phosphonic acid (ACP) and (1-amino-1-methyl)ethylphosphonic acid (AMEP), were found to be competitive inhibitors versus both ACC and bicarbonate (HCO3−) ions. The measured dissociation constants for Fe(II) and ACC clearly indicate that bicarbonate ions improve both Fe(II) and ACC binding, strongly suggesting a stabilization role for this cofactor. A structural model of tomato ACCO was constructed and used for docking experiments, providing a model of possible interactions of ACC, HCO3−, and ascorbate at the active site. In this model, the ACC and bicarbonate binding sites are located close together in the active pocket. HCO3− is found at hydrogen-bond distance from ACC and interacts (hydrogen bonds or electrostatic interactions) with residues K158, R244, Y162, S246, and R300 of the enzyme. The position of ascorbate is also predicted away from ACC. Individually docked at the active site, the inhibitors ACP and AMEP were found coordinating the metal ion in place of ACC with the phosphonate groups interacting with K158 and R300, thus interlocking with both ACC and bicarbonate binding sites. In conclusion, HCO3− and ACC together occupy positions similar to the position of 2-oxoglutarate in related enzymes, and through a hydrogen bond HCO3− likely plays a major role in the stabilization of the substrate in the active pocket.
Journal of Organic Chemistry | 2012
Filipe Gomes; Antoine Fadel; Nicolas Rabasso
α-Amino allenephosphonates were easily prepared in two steps from protected amines, propargyl alcohols, and chlorophosphites. First, ynamides were synthesized from unprotected 1-bromopropargyl alcohols using a copper(II) catalyzed coupling reaction. In the second step, the previously prepared ynamides were transformed directly to allenes through a [2,3]-sigmatropic rearrangement of propargyl phosphites. This efficient method led to the formation of a series of α-amino allenephosphonates with diverse substituents on the amine, the phosphonate, and the allene moieties.
Tetrahedron | 1991
Antoine Fadel
Abstract Cyclopropanone acetal 2a undergoes the one-pot Strecker synthesis under sonication to provide the amino nitrile 8, which after hydrolysis and catalytic hydrogenolysis, gives 1-aminocyclopropanecar☐ylic acid (ACC, 1) in good overall yield.
Phosphorus Sulfur and Silicon and The Related Elements | 2011
Nicolas Rabasso; Antoine Fadel
Abstract Synthesis of a phosphonopentapeptide enkephalin analogue was achieved from heterocyclic aminophosphonates via the coupling of Boc-Tyr-Gly-Gly-OH with phosphonodipeptide. The latter was formed by coupling Boc-Phe-OH with N-terminal α,α-disubstituted heterocyclic α-aminophosphonates. GRAPHICAL ABSTRACT
Journal of Organic Chemistry | 1992
Jean Louis Canet; Antoine Fadel; Jacques Salaün
Advanced Synthesis & Catalysis | 2011
Antoine Fadel; Frederic Legrand; Gwilherm Evano; Nicolas Rabasso
Synthesis | 1987
Antoine Fadel; Ramdane Yefsah; Jacques Salaün
Journal of Organic Chemistry | 1980
Jacques Salaün; Fatima Bennani; Jean Claude Compain; Antoine Fadel; Jean Ollivier
Tetrahedron Letters | 2010
Nicolas Rabasso; Antoine Fadel