Robust Enzymatic Resolution of 3-Fluoromandelic Acid with Lipase PS Supported on Celite
作者： Javier Mendiola , Susana García-Cerrada , Óscar de Frutos , María Luz de la Puente
DOI: 10.1021/OP300137A
关键词: Chemistry 、 Lipase 、 Mandelic acid 、 Resolution (mass spectrometry) 、 Organic media 、 Enzyme 、 Chromatography
摘要: The resolution of different mandelic acids using the lipase PS “Amano” SD enzyme is described. By supporting lyophilized over Celite, both activity and stability in organic media were significantly improved, enabling robust scale-up 3-fluoromandelic acid. methodology was extended to produce a range optically pure (R)-mandelic acids, avoiding tedious extractions or chromatography.
acs.org
sci-hub.se 参考文章(28)
Kenichi Sakai, Rumiko Sakurai, Hiroyuki Nohira, New resolution technologies controlled by chiral discrimination mechanisms. Topics in Current Chemistry. ,vol. 269, pp. 199- 231 ,(2006) , 10.1007/128_2006_097
Jose M Palomo, Gloria Muñoz, Gloria Fernández-Lorente, Cesar Mateo, Manuel Fuentes, Jose M Guisan, Roberto Fernández-Lafuente, Modulation of Mucor miehei lipase properties via directed immobilization on different hetero-functional epoxy resins: Hydrolytic resolution of (R,S)-2-butyroyl-2-phenylacetic acid Journal of Molecular Catalysis B-enzymatic. ,vol. 21, pp. 201- 210 ,(2003) , 10.1016/S1381-1177(02)00224-2
Nicole Kaftzik, Wolfgang Kroutil, Kurt Faber, Udo Kragl, Mandelate racemase activity in ionic liquids: scopes and limitations Journal of Molecular Catalysis A: Chemical. ,vol. 214, pp. 107- 112 ,(2004) , 10.1016/J.MOLCATA.2003.11.034
Toshiyuki Itoh, Yoshihito Nishimura, Nozomi Ouchi, Shuichi Hayase, 1-Butyl-2,3-dimethylimidazolium tetrafluoroborate: the most desirable ionic liquid solvent for recycling use of enzyme in lipase-catalyzed transesterification using vinyl acetate as acyl donor Journal of Molecular Catalysis B: Enzymatic. ,vol. 26, pp. 41- 45 ,(2003) , 10.1016/S1381-1177(03)00147-4
Pierric Marchand, Loı¨c Lefèbvre, Florian Querniard, Pascal Cardinaël, Guy Perez, Jean-Jacques Counioux, Gérard Coquerel, Diastereomeric resolution rationalized by phase diagrams under the actual conditions of the experimental process Tetrahedron-asymmetry. ,vol. 15, pp. 2455- 2465 ,(2004) , 10.1016/J.TETASY.2004.06.044
A. Martín, M.J. Cocero, Separation of enantiomers by diastereomeric salt formation and precipitation in supercritical carbon dioxide: Application to the resolution of mandelic acid Journal of Supercritical Fluids. ,vol. 40, pp. 67- 73 ,(2007) , 10.1016/J.SUPFLU.2006.03.018
Diana F. Colon, Simeon T. Pickard, Howard E. Smith, Optically active amines. 36. Application of the benzene chirality rule to ring-substituted mandelic acids Journal of Organic Chemistry. ,vol. 56, pp. 2322- 2326 ,(1991) , 10.1021/JO00007A016
Neide Queiroz, Mariada Graça Nascimento, Pseudomonas sp. lipase immobilized in polymers versus the use of free enzyme in the resolution of (R,S)-methyl mandelate Tetrahedron Letters. ,vol. 43, pp. 5225- 5227 ,(2002) , 10.1016/S0040-4039(02)01057-2
Cynthia Ebert, Giorgio Ferluga, Lucia Gardossi, Teresa Gianferrara, Paolo Linda, Improved lipase-mediated resolution of mandelic acid esters by multivariate investigation of experimental factors Tetrahedron-asymmetry. ,vol. 3, pp. 903- 912 ,(1992) , 10.1016/S0957-4166(00)82188-6
Ramesh Patel, Biocatalysis: Synthesis of Chiral Intermediates for Pharmaceuticals Current Organic Chemistry. ,vol. 10, pp. 1289- 1321 ,(2006) , 10.2174/138527206777698011