Laboratoire des Glucides

FRE 3517

Accueil > Équipe BIOMOL > Denis Postel

Denis PostelProfesseur
Mail : denis.postel@u-picardie.fr
Tel : 03 22 82 75 70
Fax : 03 22 82 75 60
C.V.

 

Responsable de l'équipe BIOMOL

Description des travaux de recherche

Les axes majeurs de recherche concernent la synthèse et l'utilisation de glyco-α-aminonitriles pour l'élaboration de composés d'intérêt biologique (glycoamino acides ; dérivés polyhétérocycliques ; pseudo-oligosaccharides) ainsi que la synthèse asymétrique de nucléosides modifiés, analogues azotés de TSAO (inhibiteurs non-compétitifs de la transcriptase inverse du VIH-1). Nous avons également entrepris récemment l'exploration de nouvelles voies d'accès aux alkylidènes carbènes dérivés de glucides. Ces composés sont des intermédiaires de choix pour l'obtention de cycles, principalement de type cyclopropane mais également par réaction d'insertion (C-C, C-H, O-H, O-Si) de type [1,6] ou [1,5]. L'utilisation d'intermédiaires glycocarbénoïques peut permettre un accès efficace à des composés polycycliques d'intérêt thérapeutique tels les nucléosides à conformation restreinte.

Publications

  • Synthesis of 2-aminocyclopropyl pyrrolidines from glycoaminonitriles.
    D. DECLERCK, S. JOSSE, A. NGUYEN-VAN-NHIEN, D. POSTEL.
    Tetrahedron Letters, 2009, 50 (19), 2171-2173.
  • Synthesis of 5-substituted-3,4-dihydroxycyanopyrrolidines. An easy access to polyhydroxyprolines.
    M. MOURA, S. DELACROIX, D. POSTEL, A. NGUYEN-VAN-NHIEN.
    Tetrahedron, 2009, 65 (14), 2766-2772.
  • A theoretical analysis of the Ti(IV)-catalyzed glycoaminocyanation reaction.
    E. SORIANO, J. MARCO-CONTELLES, H. DUCATEL, A. NGUYEN-VAN-NHIEN, D. POSTEL.
    Carbohydrate Research, 2008, 343 (10-11), 1835-1839.
  • Synthesis and anti-HIV1 biological activity of novel 5-ATSAO compounds.
    C. TOMASSI,  A.  NGUYEN-VAN-NHIEN,  J. L.  MARCO-CONTELLES,  J. BALZARINI,  C. PANNECOUQUE,  E. DE CLERCQ, D. POSTEL.
    Bioorganic & Medicinal Chemistry, 2008, 16 (8), 4733-4741.
  • Synthesis, anti-HIV-1 activity, and modeling studies of N-3 Boc TSAO compounds.
    C. TOMASSI, A. NGUYEN-VAN-NHIEN, J.  L. MARCO-CONTELLES, J. BALZARINI, C. PANNECOUQUE, E. DE CLERCQ, E. SORIANO, D. POSTEL.
    Bioorganic & Medicinal Chemistry Letters, 2008, 18 (7), 2277-2281.
  • Novel glycine like amino acids from glyco-α-aminonitriles as building blocks for peptide synthesis.
    H. DUCATEL, A. NGUYEN-VAN-NHIEN., D. POSTEL.
    Tetrahedron: Asymmetry, 2008, 19(1), 67-81.
  • Efficient synthesis of sugar iminopyrrolidine derivatives via an intramolecular Staudinger-aza-Wittig-type reaction.
    H. DUCATEL, A. NGUYEN-VAN-NHIEN, S. PILARD, D. POSTEL.
    Synlett, 2006, (12), 1875-1878.
  • Synthesis of 2',3'-didehydro-2',3'-dideoxynucleosides via nucleoside route.
    C. LEN, D. POSTEL.
    Current Organic Synthesis, 2006, 3(3), 261-281. 
  • Computational Analysis of Aza Analogues of [2',5'-Bis-O-(tert-butyldimethylsilyl)-β -D-ribofuranose]-3'-spiro-5''- (4''-amino-1'',2''-oxathiole-2'',2''-dioxide) (TSAO) as HIV-1 Reverse Transcriptase Inhibitors: Relevance of Conformational Properties on the Inhibitory Activity.
    E. SORIANO, A. NGUYEN-VAN-NHIEN, C. TOMASSI, D. POSTEL, J. L. MARCO-CONTELLES.
    Journal of Chemical Information and Modeling, 2006, 46(4), 1666-1677. 
  • First Synthesis and Evaluation of the Inhibitory Effects of Aza analogues of TSAO on HIV-1 Replication.
    A. NGUYEN-VAN-NHIEN, J. BALZARINI, C. TOMASSI, C. LEN, J. L. MARCO-CONTELLES, C. PANNECOUQUE, E. DE CLERCQ, D. POSTEL.
    J. Med Chem., 2005, 48(13), 4276-4284.
  • Synthesis of 4-amino-5-H-dihydroisothiazole-1,1-dioxide ring system on sugar template via carbanion-mediated sulfonamide intramolecular cyclization reactions (CSIC protocols) of glyco-α-sulfonamidonitriles.
    L. DOMINGUEZ, A. NGUYEN-VAN-NHIEN, C. TOMASSI, C. LEN, D. POSTEL, J. L. MARCO-CONTELLES.
    J. Org. Chem., 2004, 69, 843.
  • Synthesis of 1,2-O-isopropylidene-3-spiro-(4’-amino-2’,3’-dihydro-1,1-dioxide-1’,2’-isothiazolyl) -D-ribo (or -D-allo)furanose derivatives, a series of key intermediates for the preparation of new, non-natural nucleoside.
    A. NGUYEN-VAN-NHIEN, L. DOMINGUEZ, C. TOMASSI, M. DEL ROSARIO TORRES, C. LEN, D. POSTEL, J. L. MARCO-CONTELLES.
    Tetrahedron, 2004, 60, 4709-4727.
  • Enantioseparation of four cis and trans diastereomers of 2',3'-didehydro-2',3'-dideoxythymidine analogs, by high-performance liquid chromatography and capillary electrophoresis.
    E. LIPKA, A. SELOUANE, D. POSTEL, C. LEN, M.-P. VACCHER, J.-P. BONTE, C. VACCHER. 
    Journal of Chromatography, A, 2004, 1034(1-2), 161-167.
  • HPLC Separation and Determination of Enantiomeric Purity of Novel Nucleoside Analogs, on Cyclodextrin Chiral Stationary Phases, Using Reversed and Polar Organic Modes.
    E. LIPKA, V. GLACON, G. MACKENZIE, D. EWING, C. LEN, D. POSTEL, M.-P. VACCHER, J.-P. BONTE, C. VACCHER.
    Analytical Letters, 2004, 37(3), 385-398.
  • Synthesis of AZA analogues of TSAO.
    A. NGUYEN-VAN-NHIEN, D. POSTEL, C. TOMASSI, C. LEN, J. L. MARCO-CONTELLES.
    Nucleosides, nucleotides & nucleic acids, 2003, 5-8, 943-945.
  • Chemistry of sulfonate and sulfonamide stabilized carbanions – The CSIC reaction,
    D. POSTEL, A. NGUYEN-VAN-NHIEN, J. L. MARCO-CONTELLES.

    Eur. J. Org.
    Chem.
    , 2003, 19, 3713-3726.
  • 1,3-Dihydrobenzo[c]furan nucleoside analogues: additional studies of the thymine derivative.
    D. EGRON, C. PERIGAUD, G. GOSSELIN, A.-M. AUBERTIN, A. FARAJ, A. SELOUANE, D. POSTEL, C. LEN.
    Bioorganic & Medicinal Chemistry Letters, 2003, 13(24), 4473-4475.
  • A free radical approach to the synthesis of the 1,7-dioxaspiro[4,4]nonane ring system from carbohydrate templates.
    J. L. MARCO-CONTELLES, L. DOMINGUEZ, S. ANJUM, P. BALLESTEROS, E. SORIANO, D. POSTEL.
    Tetrahedron: Asymmetry, 2003, 14(19), 2865-2869.
  • Synthesis, Stability, and Biological Evaluation of 1,3-Dihydrobenzo[c]furan Analogue of d4T and its SATE Pronucleotide.
    C. LEN, A. SELOUANE, D. POSTEL, P. VILLA, A.-M. AUBERTIN, D. EGRON, G. GOSSELIN, C. PERIGAUD.
    Nucleosides, Nucleotides & Nucleic Acids, 2003, 22(5-8), 943-945.
  • On the origin of the facial selectivity of the Sharpless asymmetric dihydroxylation of styrene derivatives.
    N. MOITESSIER, C. HENRY, C. LEN, D. POSTEL, Y. CHAPLEUR.
    Journal of Carbohydrate Chemistry, 2003, 22(1), 25-34.
  • Synthesis of acyclic bis-vinyl pyrimidines: a general route to d4T via metathesis.
    D. F. EWING, V. GLACON, G. MACKENZIE, D. POSTEL, C. LEN.
    Tetrahedron, 2003, 59(7), 941-945.
  • Asymmetric synthesis of (3S) 3-benzoyloxymethylisobenzofuranone and its 3R enantiomer as analogs of α,β-butenolides.
    C. LEN, A. SELOUANE, A. WEILING, F. COICOU, D. POSTEL.
    Tetrahedron Letters, 2003, 44(4), 663-666.
  • Glyco-α-aminonitriles as intermediates in organic synthesis.
    D. POSTEL, A. NGUYEN-VAN-NHIEN, C. LEN, H. DUCATEL, C. TOMASSI.
    Journal Marocain de Chimie Heterocyclique, 2002, 1(1), 1-6. 
  • Novel conformationally restricted glycoamino acids from glyco-α-aminonitriles as potent turn mimics in peptide synthesis. 
    D. POSTEL, A. NGUYEN-VAN-NHIEN, C. LEN, H. DUCATEL. 
    Tetrahedron Lett., 2002, 43(21), 3805-3808.
  • Acyclic nucleoside analogs of 2',3'-didehydro-2',3'-dideoxynucleosides.
    V. GLACON, D. DEPRAETERE, A. SELOUANE, D. POSTEL, C. LEN.
    Journal Marocain de Chimie Heterocyclique, 2002, 1(1), 7-11.
  • Asymmetric dihydroxylation of chiral styrene derivatives: development of an analytical strategy for the determination of the diastereomeric excess.
    S. PILARD, D. RIBOUL, V. GLACON, N. MOITESSIER, Y. CHAPLEUR, D. POSTEL, C. LEN.
    Tetrahedron: Asymmetry, 2002, 13(5), 529-537.
  • A novel approach to unsaturated acyclic nucleoside analogues and the first synthesis of d4T by ring closure metathesis.
    D. EWING, V. GLACON, G. MACKENZIE, D. POSTEL, C. LEN.
    Tetrahedron Letters
    , 2002, 43(19), 3503-3505.
  • Enantiomeric d4T analogs and their structural determination.
    A. SELOUANE, C. VACCHER, P. VILLA, D. POSTEL, C. LEN.
    Tetrahedron: Asymmetry, 2002, 13(4), 407-413.
  • Synthesis of poly(dithio-, thio- and carbamoyl (thio)ester) derivatives of D-glucose.
    C. LEN, D. POSTEL, B. MEDDAH, P. VILLA, G. RONCO.
    Phosphorus, Sulfur and Silicon and the Related Elements, 2001, 173 59-65.
  • New 4-amino-5-H-2,3-dihydroisothiazole-1,1-dioxides from sugar
    α-aminonitriles using CSIC reaction.

    D. POSTEL, A. NGUYEN-VAN-NHIEN, P. VILLA, G. RONCO.
    Tetrahedron Lett.
    , 2001, 42, 593-595.
  • Novel spirohydantoins of D-allose and D-ribose derived from glyco-α-aminonitriles.
    D. POSTEL, A. NGUYEN-VAN-NHIEN, P. VILLA, G. RONCO.
    Tetrahedron Lett., 2001, 42, 1499-1502.
  • Stereoseclective synthesis of α-aminonitriles at non-anomeric positions of monosaccharided.
    D. POSTEL, A. NGUYEN-VAN-NHIEN, M. PILLON, P. VILLA, G. RONCO.
    Tetrahedron Lett., 2000, 41, 6403-6406.
  • Preparation of oligosaccharide amino-nitriles via condensation of cyanide with imine derivatives.     
    D. POSTEL, A. NGUYEN-VAN-NHIEN, M. PILLON, P. VILLA, G. RONCO.
    Fr. Demande, 2000, 23 pp.  FR  2787453  A1  20000623  Application: FR  98-15861  19981216.
  • Synthesis and Antifungal Activity of Novel Bisdithiocarbamate Derivatives of Carbohydrates against Fusarium oxysporum f. sp. lini.
    C. RAFIN, E. VEIGNIE, M. SANCHOLLE, D. POSTEL, C. LEN, P. VILLA, G. RONCO.
    Journal of Agricultural and Food Chemistry, 2000, 48(11), 5283-5287.
  • Autocleavage of O-isopropylidene protected O-phosphono- and O-thionophosphono esters of sugars.
    D. POSTEL, G. RONCO, P. VILLA.
    Journal of Carbohydrate Chemistry, 2000, 19(2), 171-192.
  • Synthesis of precursors of 2',3'-dibranched nucleosides.
    C. LEN, G. MACKENZIE, D. POSTEL, J.-P. PETIT, P. VILLA, G. RONCO.
    Journal of Nature, 1999, 11(1), 21-27.
  • Triazole and imidazole reversed nucleosides of L-idose and D-glucose.
    L. VANBAELINGHEM, P. MARTIN, D. POSTEL, G. GOETHALS, D. F. EWING, G. MACKENZIE, G. RONCO, P. VILLA.
    Nucleosides & Nucleotides, 1999, 18(4 & 5), 677-678.
  • Strategy for the preparation of 2' and 3' branched nucleosides.
    C. LEN, D. POSTEL, G. MACKENZIE, P. VILLA, G. RONCO.
    Pharmacy and Pharmacology Communications, 1999, 5(3), 165-168.
  • Synthesis of dithio-, thio- and carbamoyl ester derivatives of monosaccharides and itols.
    C. LEN, D. POSTEL, G. RONCO, P. VILLA.
    Phosphorus, Sulfur and Silicon and the Related Elements, 1998, 133 41-59.
  • 3-acetyl deoxynivalenol production in a strain of Fusarium culmorum insensitive to the fungicide difenoconazole.
    J. P. F. D'MELLO, A. M. C. MACDONALD, D. POSTEL, E. A. HUNTER.
    Mycotoxin Research, 1997, 13(2), 73-80.
  • Synthesis of bis(carbamoyl ester) derivatives of D-glucose as antifungal products.
    C. LEN, D. POSTEL, G. RONCO, P. VILLA.
    Journal of Carbohydrate Chemistry, 1997, 16(7), 1029-1049.
  • Synthesis of carbamic esters derivatives of itols: Antifungal activity against various crop diseases.
    C. LEN, D. POSTEL, G. RONCO, P. VILLA, C. GOUBERT, E. JEUFRAULT, B. MATHON, H. SIMON.
    Journal of Agricultural and Food Chemistry, 1997, 45(1), 3-6.
  • Efficient synthesis of 6-thio and 3-thio analogs of amiprilose and related compounds.
    P. VANLEMMENS, D. POSTEL, G. RONCO, P. VILLA.
    Carbohydrate Research, 1996, 289 171-178.
  • Synthesis and Antifungal Activity of Novel Bis(dithiocarbamate) Derivatives of Glycerol.
    C. LEN, A.-S. BOULOGNE-MERLOT, D. POSTEL, G. RONCO, P. VILLA, C. GOUBERT, E. JEUFRAULT, B. MATHON, H. SIMON.
    Journal of Agricultural and Food Chemistry, 1996, 44(9), 2856-2858.
  • Novel monoacetoneglucose derivatives with calcium antagonist activity.
    T. BECAERT, P. VANLEMMENS, P. VILLA, A. LAHYANI, J. LEHOUELLEUR, D. POSTEL, G. RONCO, G. BRULE.
    Bollettino Chimico Farmaceutico, 1996, 135(3), 204-207.
  • Effects of the type of heteroatom in a monosaccharide derivative on its inhibitory action on putative P-type calcium channels expressed in Xenopus oocytes.
    A. LAHYANI, F. MATIFAT, T. COLLIN, M. IDAOMAR, D. POSTEL, G. RONCO, P. VILLA, G. GRULE.
    Archives of Physiology and Biochemistry, 1996, 104(1), 43-49.
  • Synthesis of 3-S-alkyl-3-thio-D-glucose derivatives as new nonionic surfactants and calcium antagonists.
    D. POSTEL, P. VANLEMMENS, P. GODE, G. RONCO, P. VILLA.
    Carbohydrate Research, 1995, 271(2), 227-33.
  • Synthesis of antitumors O-alkyl-linked disaccharides and their surface tension and solubility in water.
    P. GOUETH, D. POSTEL, A. RAMIZ, G. RONCO, P. VILLA.
    Fr. Demande, 1994, 38 pp. FR 2701950 A1 19940902 Application: FR 93-1997 19930222.
  • Preparation of non-glycosidic linked oligosaccharides as antitumors or chelation agents.
    M. FAUVIN, P. GOUETH, P. MARTIN, D. POSTEL, G. RONCO, P. VILLA.
    Fr. Demande, 1994, 39 pp. FR 2701949 A1 19940902 Application: FR 93-1996 19930222.
  • HLB determination of 3-O-alkyl-D-glucose derivatives.
    R. BIKANGA, P. GODE, D. POSTEL, G. RONCO, P. VILLA.
    Comunicaciones presentadas a las Jornadas del Comite Espanol de la Detergencia, 1994, 25 607-18.
  • Preparation of ether-linked disaccharides having D-xylose coupled to other monosaccharides.
    P. MARTIN, B. HARMOUCH, D. POSTEL, G. RONCO, L. SPYCHALA, P. VILLA.
    Carbohydrate Research, 1994, 254 325-31.
  • Synthesis of monoesters as surfactants and drugs from D-glucose.
    P. Y. GOUETH, P. GOGALIS, R. BIKANGA, P. GODE, D. POSTEL, G. RONCO, P. VILLA.
    Journal of Carbohydrate Chemistry, 1994, 13(2), 249-72.
  • Evaluation of xylose in bagasse by analytical chemistry.
    P. MARTIN, B. HARMOUCH, J.-Y. CONAN, P.-Y. GOUETH, D. POSTEL, G. RONCO, C. ROUCH, P. VILLA.
    Journal of Nature, 1992, 4(1), 3-9.
  • Synthesis of ether-linked disaccharide and trisaccharide derivatives of the type (3-5)-D-xylan.
    M. PATRICK; J.-Y. CONAN, B. HARMOUCH, D. POSTEL, G. RONCO, C. ROUCH, P. VILLA.
    Chemistry Letters, 1994, (1), 141-4.
  • 2,4:3,5-Di-O-methylene-1-p-toluenesulfonylxylitol.
    N. RODIER, G. RONCO, R. JULIEN, D. POSTEL, P. VILLA.
    Acta Crystallographica, Section C: Crystal Structure Communications, 1993, C49(11), 2032-3.
  • 1-Deoxy-1-(N,N-dimethyldithiocarbamoyl)di-O-isopropylidene-2,3:4,5-xylitol.
    N. RODIER, P. KHODADAD, D. POSTEL, P. VILLA, G. RONCO, R. JULIEN.
    Acta Crystallographica, Section C: Crystal Structure Communications, 1993, C49(1), 159-61.
  • 6-Deoxy-6-(N,N-dimethyldithiocarbamoyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyrannose.
    N. RODIER, P. KHODADAD, D. POSTEL, P. VILLA, G. RONCO, R. JULIEN.
    Acta Crystallographica, Section C: Crystal Structure Communications, 1991, C47(6), 1336-8.

 

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