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Dive into the research topics where Antoine Fadel is active.

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Featured researches published by Antoine Fadel.


Tetrahedron-asymmetry | 2003

First synthesis of (1S,2S)- and (1R,2R)-1-amino-2-isopropylcyclobutanecarboxylic acids by asymmetric Strecker reaction from 2-substituted cyclobutanones ☆

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

1-Aminocyclopropane-1-carboxylic acid oxidase: insight into cofactor binding from experimental and theoretical studies

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

[2,3]-Sigmatropic rearrangement of ynamides: preparation of α-amino allenephosphonates.

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

A new and convenient synthesis of 1-aminocyclopropanecar☐ylic acid from cyclopropanone acetal.

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

Synthesis of an Enkephalin Analogue Containing an α,α-Disubstituted Heterocyclic Aminophosphonic Acid

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

Asymmetric construction of quaternary carbons from chiral malonates: selective and versatile total syntheses of the enantiomers of .alpha.- and .beta.-cuparenones from a common optically active precursor.

Jean Louis Canet; Antoine Fadel; Jacques Salaün


Advanced Synthesis & Catalysis | 2011

Highly Regio‐ and Stereoselective Nickel‐Catalyzed Addition of Dialkyl Phosphites to Ynamides: an Efficient Synthesis of β‐Aminovinylphosphonates

Antoine Fadel; Frederic Legrand; Gwilherm Evano; Nicolas Rabasso


Synthesis | 1987

Anhydrous Iron(III) Chloride Dispersed on Silica Gel; III.1,2 A Convenient and Mild Reagent for Deacetalization in Dry Medium

Antoine Fadel; Ramdane Yefsah; Jacques Salaün


Journal of Organic Chemistry | 1980

Reactions of the cyclopropanone hemiketal magnesium salt with some nucleophilic reagents

Jacques Salaün; Fatima Bennani; Jean Claude Compain; Antoine Fadel; Jean Ollivier


Tetrahedron Letters | 2010

Synthesis of new β- and γ-aminopyrrolidinephosphonates via 1,3-dipolar cycloaddition of substituted vinylphosphonates

Nicolas Rabasso; Antoine Fadel

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Filipe Gomes

University of Paris-Sud

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Michel Giorgi

Aix-Marseille University

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