Enantioselectivity of Candida Rugosa Lipase Toward Carboxylic Acids: A Predictive Rule from Substrate Mapping and X-Ray Crystallography

References

• Ahn N. T. Regio- and Stereo-Selectivities in Some Nucleophilic Reactions. Top. Curr. Chem. 1980; 88: 145–162
   Google Scholar
• Allenmaik S., Ohlsson A. Enantioselectivity of Lipase-Catalyzed Hydrolysis of Some 2-Chloroethyl 2-arylpropanoates Studied by Chiral Reversed-Phase Liquid Chromatography. Chirality 1992; 4: 98–102
   Google Scholar
• Battistel E., Bianchi D., Cesti P., Pina C. Enzymatic Resolution of (S)-(+)-Naproxen in a Continuous Reactor. Biotechnol. Bioeng. 1991; 38: 659–664
   PubMed Web of Science ®Google Scholar
• Bonner W. A. The Preparation, Resolution, and Absolute Configuration of α-Mercaptophenylacetic acid. J. Org. Chem. 1968; 33: 1831–1836
   Google Scholar
• Brook M. A., Chan T. H. A Simple Procedure for the Esterification of Carboxylic Acids. Synthesis 1983; 201–203.
   Google Scholar
• Brzozowski A. M., Derewenda U., Derewenda Z. S., Dodson G. G., Lawson D. M., Turkenburg J. P. A Model for Interfacial Activation in Lipases from the Structure of a Fungal Iipase-Inhibitor Complex. Nature 1991; 351: 491–494
   PubMed Web of Science ®Google Scholar
• Cambou B., Klibanov A. M. Comparison of Different Strategies for the Lipase-Catalyzed Preparative Resolution of Racemic Acids and Alcohols: Asymmetric Hydrolysis, Esterification and Transesterification. Biotechnol. Bioeng. 1984; 26: 1449–1454
   PubMed Web of Science ®Google Scholar
• Chen C. S., Fujimoto Y., Girdaukas G., Sih C. J. Quantitative Analyses of Biochemical Kinetic Resolutions of Enantiomers. J. Am. Chem. Soc 1982; 104: 7294–7299
   Web of Science ®Google Scholar
• Chen C.-S., Wu S.-H., Girdaukas G., Sih C. J. Quantitative Analyses of Biochemical Kinetic Resolution of Enantiomers. 2. Enzyme-Catalyzed Esterifications in Water-Organic Solvent Biphasic Systems. J. Am. Chem. Soc 1987; 109: 2812–2817
   Web of Science ®Google Scholar
• Colombo M., De Amici M., De Micheli C., Pitré D., Riva S. Chemoezymatic Synthesis of the Enantiomers of Iopanoic Acid. Tetrahedron: Asymmetry 1991; 2: 1021–1030
   Google Scholar
• Cygler M., Grochulski P., Kazlauskas R. J., Schrag J. D., Bouthillier F., Rubin B. (submitted) Molecular Basis for the Enantiopreference of Lipases Toward Secondary Alcohols
   Google Scholar
• Dernoncour R., Azerad R. Enantioselective hydrolysis of 2-(chlorophenoxy)propionic esters by esterases. Tetrahedron Lett. 1987; 28: 4661–4664
   Web of Science ®Google Scholar
• Feichter C, Faber K., Griengl H. Chemoenzymatic Preparation of Atrolactic and Mosher's acid using Aspergillus oryzae Protease. J. Chem. Soc, Perkin Trans. 1991; 1: 653–654
   Google Scholar
• Fulling G., Sih C. J. Enzymatic Second-Order Asymmetric Hydrolysis of Ketorolac Esters: In Situ Racemization. J. Am. Chem. Soc 1987; 109: 2845–2846
   Web of Science ®Google Scholar
• Grochulski P., Li Y., Schrag J. D., Cygler M. Two Conformational States of Candida rugosa Lipase. Protein Sci., (in press)
   Google Scholar
• Grochulski P., Bouthillier F., Kazlauskas R. J., Serreqi A. N., Schrag J. D. (submitted) Candida rugosa Lipase-Inhibitor. Complexes Simulating the Acylation and Deacylation Transition States
   Google Scholar
• Grochulski P., Li Y., Schrag J. D., Bouthillier F., Smith P., Harrison D. Insights into Interfacial Activation from an Open Structure of Candida rugosa Lipase. J. Biol. Chem. 1993; 268: 12843–12847
   PubMed Web of Science ®Google Scholar
• Gros J. J. C., Bourcier S. Absolute Configuration of 6000 Selected Compounds with One Asymmetric Carbon Atom;. George Thieme, Stuttgart 1977; 426–441
   Google Scholar
• Gu Q.-M, Chen C.-S., Sih C. J. A Facile Enzymatic Resolution Process for the Preparation of (+)-S-2-(6-methoxy-2-naphthyl)propionic acid (naproxen). Tetrahedron Lett. 1986; 27: 1763–1766
   Web of Science ®Google Scholar
• Gupta A. K., Kazlauskas R. J. Substrate Modification to Increase the Enantioselectivity of Hydrolases. A Route to Optically-Active Cyclic Allylic Alcohols. Tetrahedron: Asymmetry 1993; 4: 879–888
   Google Scholar
• Hamman S. 2-Fluoro-2-phenylpropanoic Acid: Preparation and Use as a Chiral Derivatizing Agent. J. Fluorine Chem. 1993; 60: 225–232
   Google Scholar
• Holmberg E., Holmquist M., Hedenström E, Berglund P., Norin T., Högberg H.-E. Reaction Conditions for the Resolution of 2-Methylalkanoic Acids in Esterification and Hydrolysis with Lipase from. Candida cylindracea, Appl. Microbiol. Biotechnol. 1991a; 35: 572–578
   Web of Science ®Google Scholar
• Holmberg E., Dahlen E., Norin T., Hult K. Enhanced Resolution of a Secondary Alcohol by Hydrolysis of a Bichiral Ester Catalyzed by a Lipase from. Candida cylindracea, Biocatalysis 1991b; 4: 305–312
   Google Scholar
• Holmberg E., Hult K. Alcohol Induced Reversal of Enantioselectivity in a Lipase Catalyzed Resolution of 2-Chloropropionic Acid. Biocatalysis 1992; 5: 289–296
   Google Scholar
• Jarvest R. L., Barnes R. D., Earnshaw D. L., Otoole K. J., Sime J. T., Vere Hodge R. A. Synthesis of Isotopically Chiral [13C]Peniciclovir (BRL39123) and its Use to Determine the Absolute Configurati on of Peniciclovir Triphosphate Formed in Herpes Virus Infected Cells. J. Chem. Soc, Chem. Commun. 1990; 555–556.
   Google Scholar
• Kazlauskas R. J, Weissfloch A. N. E., Rappaport A. T., Cuccia L. A. A Rule to Predict which Enantiomer of a Secondary Alcohol Reacts Faster in Reactions Catalyzed by Cholesterol Esterase, Lipase from Pseudomonas cepacia, and Lipase from. Candida rugosa, J. Org. Chem. 1991; 56: 2656–2665
   Web of Science ®Google Scholar
• Kirchner G., Scollar M. P., Klibanov A. M. Resolution of Racemic Mixtures via Lipase Catalysis in Organic Solvents. J. Am. Chem. Soc 1985; 107: 7072–7076
   Web of Science ®Google Scholar
• Kitazume T., Sato T., Ishikawa N. Enantioselective Synthesis of Monoflurorinated Malonic Acid Monoesters with Enzymes of Microbial Origin. Chem. Lett. 1984; 1811–1814.
   Google Scholar
• Kitazume T., Murata K., Ikeya T. Synthesis of the Optically Pure Monoethyl Ester of (R)-(+)-2-Fluoromalonic Acid by Use of Immobilized lipase-MY for Asymmetric Hydrolysis. J. Fluorine Chem. 1986; 31: 143–150
   Google Scholar
• Klyne W., Buckingham J. Atlas of Stereochemistry. Oxford University Press, New York 1974; 27
   Google Scholar
• Lotti M., Grandori R., Fusetti F., Longhi S., Brocca S., Tramontano A. Cloning and Analysis of Candida cylindracea Lipase Sequences. Gene 1993; 124: 45–55
   PubMed Web of Science ®Google Scholar
• Loubinoux B., Viriot-Chauveau C., Sinnes J. L. Enantioselective Preparation of 2-Alkyl-3-aryloxypropionic Acids and Esters and 3-Alkyl-4-chromanones. Tetrahedron Lett. 1992; 33: 2145–2148
   Google Scholar
• Miyamoto K., Tsuchiya S., Ohta H. Microbial Asymmetric Decarboxylation of Fluorine-Containing Arylmalonic Acid Derivatives. J. Fluorine Chem. 1992; 59: 225–232
   Google Scholar
• Miyazawa T., Takitani T., Ueji S., Yamada T., Kuwata S. Optical Resolution of Unusual Amino-Acids by Lipase-catalyzed Hydrolysis. J. Chem. Soc., Chem. Commun. 1988; 1214–1215.
   Google Scholar
• Ngooi T. K., Guo Z.-W., Sih C. J. Enantioselective Biocatalysis - Optically-Active Intermediates for Venturicidin Synthesis. Biocatalysis 1990; 3: 119–128
   Google Scholar
• Parida S., Dordick J. S. Tailoring Lipase Specificity by Solvent and Substrate Chemistries. J. Org. Chem. 1993; 58: 3238–3244
   Google Scholar
• Pottie M., Van der Eycken J., Vandewalle M., Dewanckele J. M., Röper H. Enzymatic Enantioselective Hydrolysis of 2,2-Dimethyl-13-dioxolane-4-carboxylic Esters. Tetrahedron Lett. 1989; 30: 5319–5322
   Web of Science ®Google Scholar
• Rubin B., Jamison P., Harrison D. Crystallization and Characterization of Candida rugosa Lipase. Lipases: Structure, Mechanism and Genetic Engineering, L. Alberghina, R. D. Schmid, R. Verger. VCH, New York 1991; 63–66
   Google Scholar
• Schrag J. D., Cygler M. 1.8Å Refined Structure of the Lipase from. Geotrichum candidum, J. Mol. Biol. 1993; 230: 575–591
   PubMedGoogle Scholar
• Shimada Y., Sugihara A., Tominaga Y., Iizumi T., Tsunasawa S. cDNA Molecular Cloning of Geotrichum candidum Lipase. J. Biochem. 1989; 106: 383–388
   PubMedGoogle Scholar
• Shimada Y., Sugihara A., Iizumi T., Tominaga Y. cDNA Cloning and Characterization of Geotrichum candidum lipase II. J. Biochem. 1990; 107: 703–707
   PubMedGoogle Scholar
• Wu S.-H., Guo Z.-W., Sih C. J. Enhancing the Enantioselectivity of Candida Lipase Catalyzed Ester Hydrolysis via Noncovalent Enzyme Modification. J. Am. Chem. Soc. 1990; 112: 1990–1995
   Web of Science ®Google Scholar