ChiralSEP

 Products & Services

Chiralsep offers products and technologies in the field of chiral bioactive molecules as outlined below. 
 
Key Technologies

• Enantioselective chromatography (HPLC and SFC), with Chirose® and Cyclose® CSP's.

• Enantioselective membrane separation.

• Asymmetric synthesis  : hydrogenation, hydrogen transfer, Diels-Alder.

• Chiral combinatorial chemistry resins: Chiralbeads®  with customized unichiral synthon .

• Unichiral organometallic ligand immobilization.

• Enzyme immobilization.
  -aryl propionic acid deracemization.
   
  Products

• New enantiopure unichiral synthons.

• Proprietary and customized enantioselective chromatographic supports.

• Unichiral resins for asymmetric synthesis  and chiral combinatorial chemistry.
    
  Services

• Chiral analysis resolution: enantioselective HPLC and SFC contract method development.

• Resolution of racemic mixture from grams to tons using Prep. HPLC and SFC and membrane technologies. 

• Asymmetric synthesis with Chiralbeads®   from laboratory to pilot scale.

• Contract synthesis.
   
  Registered Trademarks

• Chirose® (Enantioselective Chromatographic Supports) 

• Cyclose® (Enantioselective Chromatographic Supports) 

• Supportase® (Immobilized Enzyme Supports) 

• Chiralbeads® (Chiral Combinatorial Chemistry Resins) 

• Chiralose®

• Chiralcrown®

• Chirogel®
   
  Patents
   Click here for a list of patents and their brief description.  

ChiralSEP Publictions & Posters

CYCLOSE® CSPs

• o Liquid chromatographic resolution of enantiomers on a new chemically bonded ß-cyclodextrin stationary phase. Blondel, F., Peulon, V., Prigent, Y., Duval, R., Combret, Y.
  Poster presented at the 8^th International Symposium on Chiral Discrimination, Edimburg, Scotland, June 30^th - July 3^rd, 1996.
• o Synthesis and evaluation in HPLC of a new chiral stationary phase based on a purified ß-cyclodextrin : ß-kleptodex-2-OH. Duval, R.
  Poster presented at the "15^ièmes journées internationales sur les huiles essentielles", Digne, France, September 5^th - 7^th, 1996.
• o Etude de l'influence de différents facteurs sur l'énantiosélectivité d'une phase stationnaire chirale dérivée d'une ß-cyclodextrine. Bourgeaux, E., Lévêque, H., Duval, R., Peulon, V.
  Poster presented at the SEP'97, Paris, France, May 27^th - 29^th, 1997.
• o Purity Control of monoderivatives of ß-cyclodextrin by LC-ELSD. Caron, I., Elkakir, C., Dreux, M., Bourgeaux, E., Lévêque, H., Duval, R.
  Poster presented at the 214^th National Meeting of the American Chemical Society, Las vegas, USA, September, 7^th - 11^th, 1997.
• o Fast and easy transposition of chiral separation conditions of racemates from SFC to HPLC. Lévêque, H., Duval, R.
  Poster presented at the 5^th Meeting on Supercritical Fluids, Nice, France, March, 23^rd - 25^th, 1998.
• o Séparations chirales: transposition de la chromatographie en phase supercritique analytique vers la chromatographie en phase liquide analytique ou préparative. Lévêque, H., Duval, R., Netter, C.
  Poster presented at the 3^ième Forum des Innovations Technologiques, Paris, France, March 31^st - April 3^rd, 1998.
• o Pure monopentylated ß-cyclodextrin as chiral reagent: purity check by LC-ELSD and LC-MS. Caron, I., Elfakir, C., Dreux, M., Bourgeaux, E., Lévêque, H., Duval, R.
  Poster presented at the 9^th International Symposium on Cyclodextrins, Santiago de Compostella, Spain, May 31^st - June 3^rd, 1998.
• o Influence of pure mono-2 and mono-6-alkenyl-cyclodextrin derivatives on the enantioselectivity of new HPLC supports. Lévêque, H., Adam, N., Duval, R.
  Poster presented at the 7^th International Symposium on Preparative and Industrial Chromatography and Allied Techniques, Strasbourg, France, September 23^rd - 25^th, 1998.
• o High field N.M.R. structural studies of mono-alkenyl-ß-cyclodextrins and their use as perfectly defined cyclodextrin based selectors for chiral HPLC when linked to activated silica gel. Prigent, Y., Blondel, F., Bourgeaux, E., Combret, Y., Lévêque, H., Duval, R., Davoust, D., Combret, J.C.
  Poster presented at the 10^th International Symposium on Chiral Discrimination, Vienna, Austria, August 30^th - September 2^nd, 1998.
• o Enantioseparation of Aminoglutethimide and Thalidomide by high performance liquid chromatography or supercritical fluid chromatography on mono-2 and mono-6-O-pentenyl-ß-cyclodextrin based chiral stationary phases. Duval, R., Lévêque, H., Prigent, Y., Aboul-Enein, H.Y.
  Biomedical Chromatography, vol 15, 202-206, 2001.
• o Glycosidases et Glycosylation enzymatique de cyclodextrines. Bonnet, V., Duval, R., Rabiller, C.
  Poster presented at the "Congrès annuel CBSO", La Londe Les Maures, Var, France, May 29^th - June 1^st, 2001.
• On the necessity to use pure mono-cyclodextrin derivatives for enantioselective high performance liquid chromatography. Duval, R., Lévêque, H., François, C.
  Poster presented at the 25^th Symposium on high Performance Liquid Chromatography and Related Techniques, MECC Maastricht, The Netherlands, June 17^th - 22^nd, 2001.
• Enantioselective supercritical fluid chromatography using mono-2 and mono-6-O-pentenyl cyclodextrins as chiral selectors covalently bonded to silica gel through thioether or sulfone linkage. Duval, R., Lévêque, H.
  Poster presented at the 10^th International Symposium on Super Critical Fluid Chromatography, Extraction and Processing, Myrtle Beach, S.C., U.S.A., August 17^th - 22^nd, 2001.
• o Glycosidases and cyclodextrines glycosylation. Bonnet, V., Duval, R., Rabiller, C.
  Poster presented at BIOTRANS 2001, TU Darmstadt, Germany, September 2^nd - 7^th, 2001.
• ßHighly pure mono-2-O-pentenyl and mono-6-O-pentenyl--cyclodextrin based CSP: differentiated behavior towards racemic mixtures in HPLC depending both on the regioselectivity of the alkenyl modification on the cyclodextrin molecule and on the chemical nature of the spacer arm. Duval, R., Lévêque, H., François, C.
  Poster presented at the 2001 Eastern Analytical Symposium, Atlantic City, N.J., U.S.A., September 30^th - October 4^th, 2001.
• ßEnantioselective HPLC and SFC with mono-2-O-pentenyl and mono-6-O-pentenyl--cyclodextrin based CSP bearing thioether or sulfone functionality in the spacer arm: differentiated recognition ability towards enantiomers with complementary aspects between HPLC and SFC. Duval, R., Lévêque, H., François, C.
  Poster presented at the 2001 Eastern Analytical Symposium, Atlantic City, N.J., U.S.A., September 30^th - October 4^th, 2001.
• Cyclodextrin ("CD") based CSP's for enantioselective ("chiral") SFC and HPLC: on the necessity to control the purity of the cyclodextrin derivatives, the regioselectivity of the alkylation reaction made on the CD molecule and on the usefulness to introduce polar functions in the spacer arm. Duval, R., Lévêque, H., François, C.
  Poster presented at the 2001 Eastern Analytical Symposium, Atlantic City, N.J., U.S.A., September 30^th - October 4^th, 2001.
• o Simultaneous quantitation of nucleoside HIV-1 reverse transcriptase inhibitors by short-end injection capillary electrochromatography on a ß-cyclodextrin-bonded silica stationary phase. Mesplet, N., Morin, P., François, C., Agrofoglio, L.
  J. of Chromatog. A, 927, 161-168, 2001.

• CYCLOSE® CARBOXY: new CD encapsulating molecules

• o Method for preparing mono-, di- and tricarboxycyclodextrins, by regioselective oxidation in position 6 of native , ß or -cyclodextrins. Vignon, M.R., Fraschini, C., Duval, R.
  Patent application: FR 00 1225 published June, 31^th, 2001.

• CHIROSE® CSP

• o Potentialité, en HPLC analytique et préparative, d'une phase polymérique chirale greffée sur silice. Garnier, S., Lévêque, H., Duval, R., Combret, J.C.
  Poster presented at SEP'97, Paris France, May, 27^th - 29^th, 1997.
• o New synthesis and preparative resolution of Nornomifensine, a useful precursor for positron emission tomography studies. Guillon, J., Dallemagne, P., Lévêque, H., Duval, R., Rault, S.
  Pharmaceutical Sciences, 3, pp 325-327, 1997.
• o Fully automated preparative HPLC for the separation of racemic pharmaceutical compounds. Heems, D., Luck., B. Pichon, B., Vérette, E.,
  Poster presented at HPLC'97, Birmingham, U.K., 1997.
• o Separation Sciences: automated HPLC for preparative purifications. Heems, D., Holzhauser, R., Luck., B. Pichon, B., Vérette, E.
  International Laboratory, vol. 27, October 1997.
• o Practical aspects of preparative supercritical fluid Chromatography. Coleman, K., Boutant, R., Verillon, F.
  Poster presented at the 5^th Meeting on Supercritical Fluids, Nice, France, March 23^rd - 25^th, 1998.
• o Practical aspects of preparative supercritical fluid Chromatography. Coleman, K., Boutant, R., Verillon, F.
  Isolation and purifications, vol. 3, pp 9-19, 1999.
• o Enantioselective separation of several piperidine-2,6-dione drugs on CHIROSE C1 chiral stationary phase. Aboul-Enein, H. Y., Al-Duraïbi, I.
  Poster presented at 11^th International Symposium On Chiral Discrimination, ISCD'99, Chicago, Il, U.S.A., July 25^th - 28^th, 1999.
• o Enantioselective separation of several piperidine-2,6-dione drugs on CHIROSE C1 chiral stationary phase. Aboul-Enein, H. Y., Al-Duraïbi, I.
  Separation Sciences and Technology, 34 (15), pp 2973-2979, 1999.
• o Enantiomeric separation of Propranolol on newly developed CHIROSE C1 chiral stationary phase. Aboul -Enein, H. Y., Al-Duraïbi, I.
  Enantiomer, vol.4, pp 451-454, 1999.
• o Synthesis and structure of Flavan-4-ols and 4-methoxyflavans as new potential anticancer drugs. Pouget, C., Fagnère, C., Basly, J.P., Lévêque, H., Chulia, A.J.
  Tetrahedron, 56, 6047-6052, 2000.
• o Fully automated preparative high performance liquid chromatography using recycling technology. Boutant, R., Vérette, E.
  Pittsburgh Conference, New Orleans,LA, U.S.A. March 4^th - 9^th, 2001.
• o Macro-chiral cavities crosslinked in a three dimensional polymeric network, or MC3PN concept: unsuspected resolving abilities when used as chiral stationary phases in HPLC and SFC. Duval, R., Lévêque, H., François, C.
  Poster presented at the 2001 Eastern Analytical Symposium, Atlantic City, N.J., U.S.A., September 30^th - October 4^th, 2001.
• o efficient HPLC separation of and enantiomers of Bis(2,2'-bipyridine)(2,2'-bipyridyne-4,4'-dicarboxylate)Ruthenium^II as precursors to biologically active labelling compounds. Amouri, H., Gruselle, M., Malézieux, B., Brissard, M., Duval, R., Lévêque, H.
  Article submitted to Inorganic Chemistry, December, 2001.

• CHIRALBEADS® epoxy and derivatives

• ®CHIRALBEADS for asymmetric heterogeneous catalysis. Herault, D., Saluzzo, C., Duval, R., Lemaire, M.
  Poster presented at the 13^th International Symposium on Chirality, ISCD 2001, Orlando, Fl., U.S.A., July 15^th - 18^th, 2001.
• o CHIRALBEADS® for asymmetric heterogeneous catalysis. Herault, D., Saluzzo, C., Duval, R., Lemaire, M.
  Article submitted to Chirality, July 18^th, 2001
• o Enantiopure poly(glycidyl methacrylate-co-ethylene glycol dimethacrylate): a new material for supported catalytic asymmetric hydrogen transfer reduction. Rolland, A., Herault, D., Touchard, F., Saluzzo, C., Duval, R., Lemaire, M.
  Tetrahedron Asymmetry, 12, 811-815, 2001.
• o Enantiopure beads: a tool for asymmetric heterogeneous catalysis. Rechavi, D., Lemaire, M.
  Journal of molecular catalysis A: Chemical, 3467, 1-8, 2002: article in press.

• CHIRALBEADS® INDABOX

• o Enantioselective catalysis of Diels-Alder reactions by heterogeneous chiral bis(oxazoline) catalysts. Rolland, A., Herault, D., Touchard, F., Saluzzo, C., Duval, R., Lemaire, M.
  Journal of molecular catalysis A: Chemical, 3466, 1-9, 2002: article in press.

• ACARBOSE and new derivatives

• o Nouvelle approche pour la synthèse de l'Acarbose et dérivés. Périon, R., Lemée, L., Ferrières, V., Duval, R., Plusquellec, D.
  Poster (P 46) presented at the "XVIII^ièmes journées de la Chimie et de la Biochimie des Glucides", Ambleteuse, France, May 28^th - June 1^st, 2000.
• A new synthetic route to the trisaccharide moiety of ACARBOSE. Périon, R., Ferrières, V., Duval, R., Plusquellec, D.
  Poster presented at the "Journées d'Erlangen", Rennes, France, April 17^th - 20^th, 2001.
• o N-substituted derivatives of 4-amino-4,6-didesoxy--D-glucopyranosyl-(14)--D-glucopyranosyl-(14)--D -glucopyranose and 4-amino-4,6-didesoxy--D-glucopyranosyl-(14)--D-glucopyranosyl-(14)-ß-D-glucopyranoside and preparation method. Ferrières, V., Lemée, L., Plusquellec, D., Périon, R., Duval, R.
  Patent application FR 00 1223 published June 31^st, 2001.
• o Approche originale pour la synthèse de l'ACARBOSE et de ses analogues. Périon, R., Ferrières, V., Duval, R., Plusquellec, D.
  Poster presented at JOC 2001, Ecole Polytechnique, Palaiseau, France, September 11^th - 13^th, 2001.

List of ChiralSEP Patents

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