Institut de Chimie Moléculaire et des Matériaux d'Orsay

Scientific publications

  • Papers. 

37. " Gramicidin-S-Inspired Cyclopeptidomimetics as Potent Membrane-Active Bactericidal Agents with Therapeutic Potential" C. Hu, Q. Wen, S. Huang, S. Xie, Y. Fang, Y. Jin, R. Campagne, V. Alezra, E. Miclet, J. Zhu, Y. Wan ChemMedChem, 2021,16, 368-376.
36. " Development of Therapeutic Gramicidin S Analogues Bearing Plastic β,γ-Diamino Acids" Q. Guan, K. Chen, Q. Chen, J. Hu, K. Cheng, C. Hu, J. Zhu, Y. Jin, E. Miclet, V. Alezra, Y. Wan, ChemMedChem 2020, 15, 1089-1100.
35. " Recent Advances in the Exploration of Therapeutic Analogues of Gramicidin S, an Old but Still Potent Antimicrobial Peptide" Q. Guan, S. Huang, Y. Jin, R. Campagne, V. Alezra, Y. Wan, Journal of Medicinal Chemistry, 2019, 62, 7603-7617.
34. " Unexpected dimerization of a tripeptide comprising a β,γ-diamino acid" Y. Wan, J.-P. Baltaze, C. Kouklovsky, E. Miclet, V. Alezra, J. Pep. Sci. 2019, 25, e3143.
33. " Oxidative Coupling of Enolates by Memory of Chirality: an Original Enantioselective Synthesis of Quaternary alpha-Amino Acid Derivatives" A. Mambrini, D. Gori, R. Guillot, C. Kouklovsky, V. Alezra Chem. Commun. 2018, 54, 12742-12745.
32. "Enantioselective Synthesis of Quaternary αAmino Acids in Flow" A. Mambrini, D. Gori, R. Guillot, C. Kouklovsky, H. Kim, J.-i. Yoshida, V. Alezra, Synfacts 2018, 14, 1325.
31. "Memory of Chirality in a FlowBased System: Enantioselective Synthesis of Quaternary αAmino Acids Using Flow Microreactors" A. Mambrini, D. Gori, R. Guillot, C. Kouklovsky, H. Kim, J.-i. Yoshida, V. Alezra, European Journal of Organic Chemistry 2018, 6754-6757.
30. "Base mediated fragmentation of bicyclic dihydro-3,6-oxazines: transformation of nitroso Diels-Alder cycloadducts" R. Campagne, F. Schäkel, R. Guillot, V. Alezra, C. Kouklovsky, Org. Lett. 2018, 20, 1884-1896.
29. "β,γ-Diamino acids as building blocks for new analogues of Gramicidin S: synthesis and biological activity", Y. Wan, A. Stanovych, D. Gori, C. Kouklovsky, S. Zirah, V. Alezra, Eur. J. Med. Chem. 2018, 149, 122-128.
28. "New constrained cyclic beta,gamma-diamino acids from glutamic acid: synthesis of both diastereomers and unexpected kinetic resolution", Y. Wan, N. Auberger, S. Thétiot-Laurent, F. Bouillère, A. Zulauf, J. He, S. Courtiol-Legourd, R. Guillot, C. Kouklovsky, S. Cote Des Combes, C. Pacaud, I. Devillers, V. Alezra, European Journal of Organic Chemistry 2018, 329-34.
27. "Interfering peptides targeting protein–protein interactions: the next generation of drugs?", H. Bruzzoni-Giovanelli, V. Alezra, N. Wolff, C.-Z. Dong, P. Tuffery, A. Rebollo, Drug Discovery Today 2018, 23, 272-285.
26. "Frozen chirality of tertiary aromatic amides: access to enantioenriched tertiary alpha-amino acid or amino-alcohol without any chiral reagent ", T. T. Mai, B. Viswambharan, D. Gori, R. Guillot, J.-V. Naubron, C. Kouklovsky, V. Alezra, Chem. Eur. J. 2017, 23, 5787-5798. Highlighted by Chemistry Views http://www.chemistryviews.org/details/ezine/10543757/Frozen_Chirality_in_Organic_Synthesis.html
25."Recent progress in Memory of Chirality (MOC), and advanced chiral pool", V. Alezra, T. Kawabata, Synthesis 2016, 48, 2997-3016.
24. "Efficient synthesis of both diastereomers of beta,gamma-diamino acids from phenylalanine and tryptophane", N. Auberger, A. Stanovych, S. Thétiot-Laurent, R. Guillot, C. Kouklovsky, S. Cote des Combes, C. Pacaud, I. Devillers, V. Alezra, Amino Acids 2016, 48, 2237-2242.
23. "bêta,gamma-diamino acid: an original building block for hybrid alpha/gamma-peptide synthesis with extra hydrogen bond donating group", A. Stanovych, D. Gori, R. Guillot, C. Kouklovsky, E. Miclet, V. Alezra, Amino Acids 2014, 46, 2753-2757.
22. "Substrate control in enantio and diastereoselective aldol reaction by memory of chirality: a rapid access to enantiopure bêta-hydroxy quaternary alpha-amino acids", B. Viswambharan, D. Gori, R. Guillot, C. Kouklovsky, V. Alezra, Org. Lett. 2014, 16, 788-791.
21. "Original bêta,gamma-diamino acid as inducer of a gamma-turn mimic in short peptides", S. Thétiot-Laurent, F. Bouillère, J.-P. Baltaze, F. Brisset, D. Feytens, C. Kouklovsky, E. Miclet, V. Alezra, Org. Biomol. Chem. 2012, 10, 9660-9663.
20. "Memory of Chirality of Tertiary Aromatic Amide: Application to the Asymmetric Synthesis of (S)-alpha-MethylDOPA", T. T. Mai, B. Viswambharan, D. Gori, C. Kouklovsky, V. Alezra, J. Org. Chem. 2012, 77, 8797-8801.
19. "Absolute asymmetric synthesis of tertiary alpha-amino acids", T. T. Mai, M. Branca, D. Gori, R. Guillot, C. Kouklovsky, V. Alezra, Angew. Chem. Int. Ed. 2012, 51, 4981-4984.
18. "Constrained alpha/gamma-peptide: a new stable extended structure in solution without any hydrogen bond and characterized by a four-fold symmetry", F. Bouillère, D. Feytens, D. Gori, R. Guillot, C. Kouklovsky, E. Miclet, V. Alezra, Chem. Commun. 2012, 48, 1982-1984.
17. "Foldamers containing gamma-amino acid residue or analogues: structural features and applications", F. Bouillère, S. Thétiot-Laurent, C. Kouklovsky, V. Alezra, Amino Acids 2011, 41, 687-707.
16. "Access to bêta,gamma-diamino acids. Application to the synthesis of 3-deoxyaminostatine", F. Bouillère, R. Guillot, C. Kouklovsky, V. Alezra, Org. Biomol. Chem. 2011, 9, 394-399.
15. "Memory of Chirality of Tertiary Aromatic Amides: a Simple and Efficient Method for the Enantioselective Synthesis of Quaternary alpha-Amino Acids", M. Branca, S. Pena, D. Gori, R. Guillot, V. Alezra, C. Kouklovsky, J. Am. Chem. Soc. 2009, 131, 10711-10718.
14. "Aminoacid homologation by the Blaise reaction: a new entry into nitrogen heterocycles", C. T. Hoang, F. Bouillère, S. Johannesen, A. Zulauf, C. Panel, D. Gori, A. Pouilhès, V. Alezra, C. Kouklovsky, J. Org. Chem. 2009, 74, 4177-4187.
13. "Enantioselective Synthesis of Quaternary L-Valine Derivatives", M. Branca, D. Gori, R. Guillot, V. Alezra, C. Kouklovsky, Synfacts 2008, 731.
12. "Tertiary Aromatic Amide for Memory of Chirality : Access to Enantioenriched alpha-Substituted Valine", M. Branca, D. Gori, R. Guillot, V. Alezra, C. Kouklovsky, J. Am. Chem. Soc. 2008, 130, 5864-5865.
11. "Accurate conformation analysis in solution: NMR and DFT/PCM study of the S-3-(1-naphthoyl)-4-isopropyl-2,2-dimethyloxazolidin-5-one in CDCl3", M. Branca, V. Alezra, C. Kouklovsky, P. Archirel, Tetrahedron 2008, 64, 1743-1752.
10. "3-aminopyrrolidines from a-aminoacids: total synthesis of (+)-nemonapride from D-alanine", C. T. Hoang, V. H. Nguyen, V. Alezra, C. Kouklovsky, J. Org. Chem. 2008, 73, 1162-1164.
9. "A stereoselective entry to 1,2-diamines by Zinc-mediated homologation of alpha-aminoacids" C. T. Hoang, V. Alezra, R. Guillot, C. Kouklovsky, Org. Lett. 2007, 9, 2521-2524.
8. "[CpRu((R)‑BINOP‑F)(H2O)][SbF6], a new Fluxional Chiral Lewis Acid Catalyst : Synthesis, Dynamic NMR , Asymmetric Catalysis and Theoretical Studies" V. Alezra, G. Bernardinelli, C. Corminboeuf, U. Frey, E. P. Kündig, A. E. Merbach, C. M. Saudan, F. Viton, J. Weber, J. Am. Chem. Soc. 2004, 126, 4843-4853.
7. "(R,R)-1,2-Diphenyl-1,2-[di(pentafluorophenyl)-phosphanoxy]ethane", E. P. Kündig, V. Alezra, Electronic Encyclopedia of Reagents for Organic Synthesis 2002, L. Paquette, Ed., Wiley. Voir http://onlinelibrary.wiley.com/o/eros/articles/rn00057/frame.html.
6. "[(Indenyl)Ru(BIPHOP-F)]+ : a Lewis Acid catalyst that controls both the diene and the dienophile facial selectivity in Diels-Alder reactions", E. P. Kündig, C. M. Saudan, V. Alezra, F. Viton, G. Bernardinelli, Angew. Chem. Int. Ed. 2001, 40, 4481-4485.
5. "The origin of chemical and configurational stability of chiral-non racemic aziridine tert-butyl ester anions", V. Alezra, M. Bonin, L. Micouin, C. Policar, H.-P. Husson, Eur. J. Org. Chem. 2001, 2589-2594.
4. "Asymmetric synthesis of quaternary tetrahydroisoquinoline-3-carboxylic acid derivatives", V. Alezra, M. Bonin, L. Micouin, H.-P. Husson, Tetrahedron Lett. 2001, 42, 2111-2113.
3. "Asymmetric functionalization of a chiral non-racemic oxazolidine ester enolate. A new route towards the preparation of quaternary serine esters", V. Alezra, M. Bonin, A. Chiaroni, L. Micouin, C. Riche, H.-P. Husson, Tetrahedron Lett. 2000, 41, 1737-1740.
2. "Fast ester cleavage of sterically hindered alpha- and bêta-aminoesters under non aqueous conditions. Application to the kinetic resolution of aziridine esters", V. Alezra, C. Bouchet, M. Bonin, L. Micouin, H.-P. Husson, Tetrahedron Lett. 2000, 41, 655-658.
1. "Practical preparation and substitution of configurationally stable aziridinyl ester anions", V. Alezra, M. Bonin, L. Micouin, H.-P. Husson, Tetrahedron Lett. 2000, 41, 651-654.

 

  • Patents:

"Chitin and method for chemically obtaining chitin and/or chitosan", C. Socolsky, S. Laurent, B. Lorette, V. Alezra, C. Le Berre, N. Berezina, 2019, EP3724237 (A1), WO2019115969 (A1).  
"Chitin and process for producing chitin and/or chitosan by the enzymatic and chemical pathway"L. Sanchez, C. Socolsky, V. Alezra, C. Le Berre, B. Lorette, S. Laurent, N. Berezina, 2019, EP37242347 (A1), WO2019115970 (A1).
"New foldamers, a method of preparing the same and their use as inhibitors of protein-protein interactions", F. Bouillère, D. Feytens, C. Kouklovsky, E. Miclet, V. Alezra, 2011, PCT/FR2011/052154.
 
  • Book:

"Toute la chimie pour bien commencer sa licence", V. Alezra, Ed. DeBoeck supérieur, 2018.
 
  • Plenary lectures:

9. Présentation de l’entreprise Ynsect,  Journée des jeunes talents de la chimie en Ile de France, Paris, September 12 2019.
8. "From natural amino-acids to non natural ones and peptides :synthesis and applications",  2018 Chinese Conference on Research and Development Technologies of Delivery Systems of Traditional Chinese Medicine, Nanchang, China, June 23-24 2018.
7. "From Memory of Chirality to Frozen Chirality: original asymmetric methods for the synthesis of non proteinogenic α-amino acids", RCOM (Rencontres de Chimie Organique de Marseille), Marseille, Mai 24-25 2018.
6. Plenary lecture at GECO 57 (August 21-26 2016, Ascain, France) http://geco57.sciencesconf.org/resource/page/id/3
5. "Non proteinogenic amino acids : asymmetric synthesis and use as building blocks for foldamers", plenary lecture at French-Japanese Symposium on Medicinal and Fine Chemistry in Lyon, September 14-17, 2014. http://fjs2014.univ-lyon1.fr/fr/pages/fjs-2014-program.
4. "From Memory of Chirality to Frozen Chirality: original methods for the enantioselective synthesis of amino acids", plenary lecture at 10th International Symposium on Carbanion Chemistry (ISCC-10) in Kyoto September 23-26 2013. http://kuchem.kyoto-u.ac.jp/shuyu/iscc10/invited_speakers.html
3. "Non proteinogenic amino acids : asymmetric synthesis and use as building blocks for foldamers", French-Indian symposium IFCOS VIII, Goa, India, April 1-3 2013.
2. " Synthèse asymétrique d'acides alpha-aminés quaternaires : des méthodes classiques à la mémoire de chiralité", Journées de Chimie ENS/X/ESPCI ParisTech, Ecole Supérieure de Physique et de Chimie Industrielles de la ville de Paris, Mai 7 2010.
1. "La mémoire de chiralité : une nouvelle voie de synthèse d'acides a-aminés quaternaires énantiomériquement enrichis", Journée Section Ile-de-France de la SFC, Paris, June 4 2008.

 

  • Invited seminars

28. "From natural amino-acids to non natural ones and peptides :synthesis and applications",  Life Science and Engineering School, Southwest Jiaotong University, Chengdu, China, June 21 2018.
27. "Non proteinogenic amino acids: asymmetric syntheses and use as building blocks for foldamers", ECPM, Strasbourg, June 9 2016.
26. "Non proteinogenic amino acids: asymmetric syntheses and use as building blocks for foldamers", Ecole Nationale Supérieure de Chimie, Mulhouse, June 8 2016.
25. "Non proteinogenic amino acids: asymmetric syntheses and use as building blocks for foldamers", Université Pierre et Marie Curie, June 29 2015.
24. "Non proteinogenic amino acids: syntheses and applications", University of Marburg, Allemagne, June 15 2015.
23. "Non proteinogenic amino acids: syntheses and applications", Kyushu University, Fukuoka, February 4 2015.
22. "Non proteinogenic amino acids: syntheses and applications", Nagasaki University, Nagasaki, February 3 2015.
21. "Non proteinogenic amino acids: syntheses and applications", Katsura Campus of Kyoto University, Kyoto, February 2 2015.
20. "Non proteinogenic amino acids: syntheses and applications", main Campus of Kyoto University, Kyoto, January 29 2015.
19. "Non proteinogenic amino acids: syntheses and applications", Shibura Institute of Technology, Tokyo, January 22 2015.
18. "Non proteinogenic amino acids: syntheses and applications", Tokyo University of Science, Tokyo, January 21 2015.
17. "Non proteinogenic amino acids: syntheses and applications", Tohoku University, Sendai, January 20 2015.
16. "Non proteinogenic amino acids: syntheses and applications", Chiba University, Tokyo, January 19 2015.
15. "Acides aminés non protéinogènes : synthèses et applications", BioCIS, Faculté de Pharmacie, Chatenay-Malabry, November 21 2013.
14. "Acides aminés non protéinogènes : synthèses et applications", ENSCP, Paris, November 7 2013.
13. "Non proteinogenic amino acids : asymmetric synthesis and use as building blocks for foldamers", Université de Kyoto, Japon, September 27 2013.
12. "Non proteinogenic amino acids : asymmetric synthesis and use as building blocks for foldamers", Indian Institute of Chemical Technology, Hyderabad, Inde, April 5 2013.
11. "Acides aminés non protéinogènes : synthèses et applications", IRCOF, Rouen, March 22 2013.
10. "Acides aminés non protéinogènes : synthèses et applications", ICSN, Gif-sur-Yvette, February 14 2013.
9. "Acides aminés non protéinogènes : synthèses et applications", Unité de recherche exploratoire-Sanofi, Chilly-Mazarin, November 15 2012.
8. "La mémoire de chiralité et la chiralité gelée, deux nouvelles approches pour la synthèse asymétrique d'acides α-aminés", ENS-Ulm, October 19 2012.
7. "La chiralité", vulgarization lecture for International year of chemistry, at secondary school Blaise Pascal (Orsay) March 31 and June 9 and at secondary school Chaptal (Paris), Mai 6 2011.
6. "Acides aminés non protéinogéniques : synthèses et applications", laboratoire SOSCO, Université de Cergy-Pontoise, June 14 2011.
5. "Stereoselective synthesis of amino-acids: new methods and new targets", Institute of Organic Chemistry and Biochemistry ASCR, Prague, République Tchèque, October 2 2009.
4. "Synthèse stéréosélective d’acides aminés : nouvelles méthodes et nouvelles cibles", CEA-Saclay, March 4 2009.
3. "Synthèse stéréosélective d’acides aminés : nouvelles méthodes et nouvelles cibles", Faculté de Pharmacie – Paris V, November 6 2008.
2. "Développement et applications d'acides de Lewis chiraux. Application de la réaction de Blaise à la synthèse d'acides b,g-diaminés", Ecole Polytechnique, laboratoire DCPH, June 13 2005.
1. "Développement et applications d’acides de Lewis chiraux basés sur des métaux de transition", Faculté de Pharmacie – Paris V, November 15 2002.