Kazlauskas' Group Publications

2009
95. T. Yin, P. Bernhardt, K.L. Morley, Y. Jiang, J.D. Cheeseman, V. Purpero, J.D. Schrag, R.J. Kazlauskas “Switching catalysis from hydrolysis to perhydrolysis in P. fluorescens esterase” 2009, submitted.
94. S.K. Padhi, R Fujii, G.A. Legatt, S.L. Fossum, R. Berchtold, R.J. Kazlauskas "Switching from an esterase mechanism to a hydroxynitrile lyase mechanism requires only two amino acid substitutions" 2009, submitted.
93. J.-H. Park, H.-J. Ha, W. K. Lee, T. Généreux-Vincent, R. J. Kazlauskas "Molecular basis for the stereoselective ammoniolysis of N-alkyl aziridine-2-carboxylates catalyzed by Candida antarctica lipase B" ChemBioChem 2009, 10, accepted.
92. R. J. Kazlauskas, U. T. Bornscheuer "Finding better protein engineering strategies" Nature Chem. Biol. 2009, 5, 526-529. more...
91. S. Duncan, Q. Jing, A. Katona, R. J. Kazlauskas, J. Schilling, U. Tschirner, W. Wafa AlDajani “Increased saccharification yields from aspen biomass upon treatment with enzymatically generated peracetic acid." Appl. Biochem. Biotechnol. 2009, in press. more...
90. H. Jochens, K. Stiba, C. Savile, R. Fujii, J.-G. Yu, T. Gerassenkov, R. J. Kazlauskas, U. T. Bornscheuer “Converting an esterase into an epoxide hydrolase” Angew. Chem. Intl. Ed. 2009, 48, 3532-3535. more...
89. Q. Jing, K. Okrasa, R. J. Kazlauskas "Stereoselective hydrogenation of olefins using rhodium-substituted carbonic anhydrase – a new reductase" Chem. Eur. J. 2009, 15, 1370-1376. more...
88. Qing Jing, Krzysztof Okrasa, Romas J. Kazlauskas “Manganese-substituted a-carbonic anhydrase as an enantioselective peroxidase” Topics Organometall. Chem. 2009, 25, 45-61. more...

2008
87. P. Mugford, U. Wagner, Y. Jiang, K. Faber, R. Kazlauskas “Enantiocomplementary enzymes: Classification, molecular basis for their reversed enantiopreference and prospects for mirror-image biotransformations” Angew. Chem. Intl. Ed. 2008, 47, 8782-8793. more...
86. J.T. Gorke, F. Srienc, R.J. Kazlauskas “ Enzymatic biotransformations in deep eutectic solvents" Chem. Commun. 2008, 1235-1237. more...
85. Q. Jing, R.J. Kazlauskas "Determination of absolute configurations of secondary alcohols by lipase-catalyzed kinetic resolutions" Chirality, 2008, 20, 724-735. more...

2007
84. J.T. Gorke, K. Okrasa, A. Louwagie, R.J. Kazlauskas, F. Srienc “ Enzymatic synthesis of poly(hydroxyalkanoates) in ionic liquids” J. Biotechnol. 2007, 132, 306-313. more...

2006
83. R.J. Kazlauskas, "News & Views: Engineering a multipurpose catalyst" Nature Chem. Biol. 2006, 2, 514-515. more...
82. C.K. Savile, R.J. Kazlauskas, “The 3-(3-pyridine)propionyl anchor group for protease-catalyzed resolutions: p-toluenesulfinamide and sterically hindered secondary alcohols” Adv. Synth. Catal. 2006, 348, 1183-1192. more...
81. K. Okrasa, R.J. Kazlauskas, “Manganese carbonic anhydrase as an enantioselective epoxidation of olefins with hydrogen peroxide” Chem. Eur. J. 2006, 11, 1587-1596. more...
80. I. Lavandera, S. Fernández, J. Magdalena, M. Ferrero, C.K. Savile, H. Grewal, R.J. Kazlauskas, V. Gotor, “Molecular basis for the unusual regioselectivity of lipase from Pseudomonas cepacia toward the secondary alcohol of 2’-deoxynucleosides” ChemBioChem, 2006, 7, 1381-1390. more...
79. A. Nisole , F.-X. Lussier, K.L. Morley, F. Shareck, R.J. Kazlauskas, C. Dupont, J.N. Pelletier “Secretion of Streptomyces lividans acetylxylan esterase A in Escherichia coli for rapid detection of activity” Prot. Express. Purif. 2006, 46, 274-284. more...
78. K.L. Morley, G. Chauve, R.J. Kazlauskas, C. Dupont, F. Shareck, R.H. Marchessault, “Acetyl xylan esterase activity on chitin and chitosan substrates” Carbohydr. Polym. 2006, 63, 310-315. more...

2005
77. U.T. Bornscheuer, R.J. Kazlauskas, Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations, 2nd edition, Wiley-VCH: Weinheim, 2005. more...
76. R.J. Kazlauskas, “Quantitative assay of hydrolases for activity and selectivity using color changes” in Enzyme Assays: High-throughput Screening, Genetic Selection and Fingerprinting, J.-L. Reymond, Ed., Wiley-VCH: Weinheim, 2005, 17-39. more...
75. R.J. Kazlauskas "News & Views: Biological Chemistry: Enzymes in Focus" Nature 2005, 436, 1096-1097. more...
74. C.K. Savile, R.J. Kazlauskas “How substrate solvation contributes to the enantioselectivity of subtilisin toward secondary alcohols” J. Am. Chem. Soc. 2005, 127, 12228-12229. more...
73. P.F. Mugford, V.P. Magloire, R.J. Kazlauskas, “Unexpected subtilisin-catalyzed hydrolysis of a sulfinamide bond in preference to a carboxamide bond in N-acyl sulfinamides” J. Am. Chem. Soc. 2005, 127, 6536-6537. more...
72. P. Bernhardt, K. Hult, R.J. Kazlauskas, “Molecular basis for perhydrolase activity in a/b hydrolases” Angew. Chem. Intl. Ed. 2005, 44, 2742-2746. more...
71. R.J. Kazlauskas, “Enhancing catalytic promiscuity for biocatalysis” Curr. Opin. Chem. Biol. 2005, 9, 195-201. more...
70. K.L. Morley, R. J. Kazlauskas, “Improving enzyme properties: when are closer mutations better?” Trends Biotechnol. 2005, 23, 231-237. more...
69. I. Lavandera, S. Fernández, J. Magdalena, M. Ferrero, R.J. Kazlauskas, V. Gotor,, “An inverse substrate orientation for the regioselective acylation of 3',5'-diaminonucleosides catalyzed by Candida antarctica lipase B?” ChemBioChem 2005, 6, 1381-1390. more...
68. A. Mezzetti, J. Schrag, C.S. Cheong, R.J. Kazlauskas, “Mirror-image packing in enantiomer discrimination: Molecular basis for the enantioselectivity of Burkholderia cepacia lipase toward 2-methyl-3-phenyl-1-propanol” Chem. Biol. 2005, 12, 427-437. more...
67. C.K. Savile, V.P. Magloire, R.J. Kazlauskas, “Subtilisin-catalyzed resolution of N-acyl arylsulfinamides” J. Am. Chem. Soc. 2005, 127, 2104-2113. more...
66. S. Park, K. Morley, G.P. Horsman, M. Holmquist, K. Hult, R.J. Kazlauskas, “Focusing mutations into the P. fluorescens esterase binding site increases enantioselectivity more effectively than random mutagenesis” Chem. Biol., 2005, 12, 45-54. more...
65. J.D. Cheeseman, A.D. Corbett, J.L. Gleason, R.J. Kazlauskas, “Receptor-assisted combinatorial chemistry: thermodynamics and kinetics in drug discovery” Chem. Eur. J. 2005, 10, 1708-1716. more...

2004
64. K. L. Morley, V. P. Magloire, C. Guerard, R. J. Kazlauskas, “Parallel synthesis of esters by solution-phase acylation of alcohols with acid chlorides using solid-supported reagents to eliminate traditional purification” Tetrahedron: Asymmetry 2004, 15, 3005-3009. more...
63. U. T. Bornscheuer, R. J. Kazlauskas, “Catalytic promiscuity in biocatalysis: using old enzymes to form new bonds and follow new pathways” Angew. Chem. Intl. Ed. 2004, 43, 6032-6040. more...
62. N. Somers, R.J. Kazlauskas, "Mapping the substrate selectivity and enantioselectivity of esterases from thermophiles" Tetrahedron: Asymmetry, 2004, 15, 2991-3004. more...
61. J.D. Cheeseman, A. Tocilj, J.D. Schrag, R.J. Kazlauskas, “X-Ray crystal structure of an aryl esterase from Pseudomonas fluorescens” Acta Crystallogr. D 2004, D60, 1237-1243. more ... [July 2004 cover picture]
60. P.F. Mugford, S.M. Lait, B.A. Keay, R.J. Kazlauskas, “Enantiocomplementary enzymatic resolution of the chiral auxiliary cis,cis-6-(2,2-dimethylpropanamido)spiro[4.4]-nonan-1-ol and the molecular basis for the high enantioselectivity of subtilisin Carlsberg” ChemBioChem, 2004, 5, 980-987. more ...
59. A.D. Corbett, J.D. Cheeseman, R.J. Kazlauskas, J.L. Gleason, “Pseudo-dynamic combinatorial libraries: a new receptor-assisted approach for drug discovery” Angew. Chem. Intl. Ed. 2004, 43, 2432-2436. more ... Flagged by the reviewers as a ‘very important paper’.

2003
58. A. Mezzetti, C. Keith, R.J. Kazlauskas, “Highly enantioselective kinetic resolution of primary alcohols of the type Ph-X-CH(CH3)CH2OH by Pseudomonas cepacia lipase. Effect of acyl chain length and solvent” Tetrahedron: Asymmetry 2003, 14, 3917-3924. more ...
57. S. Park, F. Viklund, R. J. Kazlauskas, K. Hult “Vacuum-driven lipase-catalyzed direct condensation of L-ascorbic acid and fatty acids in ionic liquids: synthesis of natural surface-active antioxidants” Green Chem. 2003, 5, 715-719. more ...
56. S. Park, R. J. Kazlauskas “Biocatalysis in ionic liquids – advantages beyond green technology” Curr. Opin. Biotechnol. 2003, 14, 432-437. more ...
55. S. Park, E. Forró, H. Grewal, F. Fülöp, R.J. Kazlauskas “Molecular basis for the enantioselective ring opening of b-lactams catalyzed by Candida antarctica lipase B” Adv. Synth. Catal. 2003, 345, 986-995. more...
54. G.P. Horsman, A.M.F. Liu, E. Henke, U.T. Bornscheuer, R.J. Kazlauskas “Mutations in distant residues moderately increase the enantioselectivity of Pseudomonas fluorescens esterase toward methyl 3-bromo-2-methylpropanoate and ethyl 3-phenylbutyrate” Chem. Eur. J. 2003, 9, 1933-1939. more...
53. “Ionic liquids create new opportunities for nonaqueous biocatalysis: acylation of glucose and ascorbic Acid” in Ionic Liquids in Green Chemistry, Prospects and Opportunities, Rogers, R.D.; Seddon, K.R., Eds., ACS Symposium Series, 2003, 856, 225-238.

2002
52. J.D. Cheeseman, A.D. Corbett, R. Shu, J. Croteau, J.L. Gleason, R.J. Kazlauskas “Amplification of screening sensitivity through selective destruction: theory and screening of a library of carbonic anhydrase inhibitors” J. Am. Chem. Soc. 2002, 124, 5692-5701. more ... (Highlighted in Nature Rev. Drug Discov. 2002, 1, 412; Curr. Opin. Chem. Biol. 2002, 6, 407-408; Canadian Chem. News 2002, Sept. pp. 19-20; chosen as a key paper on the ‘Faculty of 1000’ website)

2001
51. R.J. Kazlauskas, “Modeling - a tool for experimentalists” Science, 2001, 293, 2277-2279. more ... (invited Tech.Sight essay about molecular modeling)
50. S. Park, R. J. Kazlauskas, “Improved preparation and use of room temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations, J. Org.Chem. 2001, 66, 8395-8401. more ...
49. D.G. Gascoyne, H.L. Finkbeiner, K.P. Chan, J.L. Gordon, K.R. Stewart, R.J. Kazlauskas “Molecular basis for enantioselectivity of lipase from Chromobacterium viscosum toward the dibutanoate ester of 2,3-dihydro-3-(4’-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol” J. Org. Chem., 2001, 66, 3041-3048. more...
48. A. Man Fai Liu, N.A. Somers, R. J. Kazlauskas, T.S. Brush, F. Zocher, M. Enzelberger, U.T. Bornscheuer, G.P. Horsman, A. Mezzetti, C. Schmidt-Dannert, R.D. Schmid, “Mapping the substrate selectivity of new hydrolases using colorimetric screening: lipases from Bacillus thermocatenulatus and Ophiostoma piliferum, esterases from Pseudomonas fluorescens and Streptomyces diastatochromogenes” Tetrahedron: Asymmetry 2001, 12, 545-556. more ...
47. A.N.E. Weissfloch, R.J. Kazlauskas, “Choosing Hydrolases for Enantioselective Reactions Involving Alcohols Using Empirical Rules” in Methods in Biotechnology, Vol 15: Enzymes in Nonaqueous Solvents: Methods and Protocols, E.N. Vulfson, P.J. Halling, H.L. Holland, Eds., Humana Press: Totowa, NJ, 2001, 243-259.

2000
46. R.J. Kazlauskas, "Molecular modeling and biocatalysis – explanations, predictions, limitations, and opportunities" Curr. Opin. Chem. Biol. 2000, 4, 81-88. more ...
45. A.N.E. Weissfloch, R.J. Kazlauskas, "Molecular basis for empirical rules that predict the stereoselectivity of hydrolases" in Enzymes in Action: Green Solutions for Chemical Problems, Zwannenburg, B., Mikolajczyk, M., Kielbasinski, P., Eds., NATO Science Series, Kluwer Academic: Dordrecht, 2000, pp. 43-69.

before 2000
44. L.E. Janes, A. Cimpoia, R.J. Kazlauskas, “Protease-mediated separation of cis and trans diastereomers of 2-(R,S)-benzyloxymethyl-4-(S)-carboxylic acid-1,3-dioxolane methyl ester: intermediates for the synthesis of dioxolane nucleosides” J. Org. Chem. 1999, 64, 9019-9029. more...
43. M. Zhang, R. Kazlauskas, "First preparation of enantiopure indane monomer, (S)-(–)- and (R)-(+)-2,3-dihydro-3-(4’-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol, via a unique enantio- and regioselective enzymatic kinetic resolution" J. Org. Chem. 1999, 64, 7498-7503.
42. H.K. Weber, H. Weber, R.J. Kazlauskas, "’Watching’ lipase-catalyzed acylations using 1H-NMR: competing hydrolysis of vinyl acetate in dry organic solvents." Tetrahedron: Asymmetry 1999, 10, 2635-2638.
41. W.V. Tuomi, R.J. Kazlauskas, "Molecular basis for enantioselectivity of lipase from Pseudomonas cepacia toward primary alcohols. Modeling, kinetics and chemical modification of Tyr29 to increase or decrease enantioselectivity" J. Org. Chem. 1999, 64, 2638-2647.
Book: Uwe T. Bornscheuer, Romas J. Kazlauskas Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations Wiley-VCH: Weinheim, 1999.
40. R. J. Kazlauskas, U. T. Bornscheuer “Biotransformations with Lipases” Biotechnology, 2nd ed., Vol. 8a Biotransformations I, David R. Kelly, Ed. VCH: Weinheim, 1998, 37-191.
39. R. J. Kazlauskas, H. K. Weber "Improving hydrolases for organic synthesis" Curr. Opin. Chem. Biol., 1998, 2, 121-126.
38. L. E. Janes, A. C. Löwendahl, R. J. Kazlauskas, “Rapid quantitative screening of hydrolases using pH indicators. Finding enantioselective hydrolases.” Chem. Eur. J. 1998, 4, 2324-2331.
37. L. E. Janes, R. J. Kazlauskas, "Empirical rules for the enantiopreference of lipase from Aspergillus niger toward secondary alcohols and carboxylic acids, especially a-amino acids" Tetrahedron: Asymmetry 1997, 8, 3719-3734.
36. L. E. Janes, R. J. Kazlauskas, "Quick E. A Fast Spectrophotometric Method to Measure the Enantioselectivity of Hydrolases" J. Org. Chem. 1997, 62, 4560-4561.
35. R. J. Kazlauskas, A. N. E. Weissfloch “A Structure-Based Rationalization of the Enantiopreference of Subtilisin toward Secondary Alcohols and Isosteric Primary Amines” J. Mol. Catal. B Enz. 1997, 3, 65-72.
34. G. A. R. Nobes, R. J. Kazlauskas, R. H. Marchessault, "Lipase-Catalyzed Ring Opening Polymerization of Lactones: A Novel Route to Poly(hydroxyalkanoates)." Macromolecules 1996, 29, 4829-4833.
33. A. N. E. Weissfloch, R. J. Kazlauskas, "Enantiopreference of Lipase From Pseudomonas Cepacia toward Primary Alcohols" J. Org. Chem. 1995, 60, 6959-6969.
32. A. N. Serreqi, R. J. Kazlauskas, "Kinetic Resolution of Sulfoxides Catalyzed by Cholesterol Esterase: Substrate Mapping and an Empirical Rule" Can. J. Chem. 1995, 73, 1357-1367.
31. I. J. Colton, S. N. Ahmed, R. J. Kazlauskas, "Isopropanol Treatment Increases Enantioselectivity of Candida rugosa Lipase toward Carboxylic Acid Esters" J. Org. Chem. 1995, 60, 212-217.
30. A. N. Serreqi, R. J. Kazlauskas, "Kinetic Resolution of Phosphines and Phosphine Oxides Catalyzed by Hydrolases" J. Org. Chem. 1994, 59, 7609-7615.
29. I. J. Colton, R. J. Kazlauskas, "Dicarboxylic Acids Link Proton Transfer across a Liq-uid Membrane to the Synthesis of an Acyl Phosphate. A Model for P-type H+-ATPase." J. Org. Chem. 1994, 59, 3626-3635.
28. G. Caron, R. J. Kazlauskas, "Isolation of Racemic 2,4-Pentanediol and 2,5-Hexanediol from Commercial Mixtures of Meso and Racemic Isomers by way of Cyclic Sulfites." Tetrahedron: Asymmetry 1994, 5, 657-664.
27. S. N. Ahmed, R. J. Kazlauskas, A. H. Morinville, P. Grochulski, J. D. Schrag, M. Cygler, "Enantioselectivity of Candida Rugosa Lipase toward Carboxylic Acids: A Predictive Rule from Substrate Mapping and X-Ray Crystallography" Biocatalysis, 1994, 9, 209-225.
26. M. C. Ng-Youn-Chen, A. N. Serreqi, Q. Huang, R. J. Kazlauskas, "Ki-netic Resolution of Pipecolic Acid Using Partially-Purified Lipase from Aspergillus niger" J. Org. Chem. 1994, 59, 2075-2081.
25. R. J. Kazlauskas, "Elucidating Structure-Mechanism Relationships in Lipases: Prospects for Predicting and Engineering Catalytic Properties" Trends Biotechnol. 1994, 12, 464-472; Erratum, 1995, 13, 195.
24. M. Cygler, P. Grochulski, R. J. Kazlauskas, J. D. Schrag, F. Bouthillier, B. Rubin, A. N. Serreqi, A. K. Gupta, "Molecular Basis for the Enantiopreference of Lipases toward Secondary Alcohols" J. Am. Chem. Soc. 1994, 116, 3180-3186. [Highlighted in Nature Structural Biology 1994, 1, 569-72.]
23. P. Grochulski, F. Bouthillier, R. J. Kazlauskas, A. N. Serreqi, J. D. Schrag, E. Ziomek, M. Cygler, "Candida rugosa Lipase-Inhibitor Complexes Simulating the Acylation and Deacylation Transition States" Biochemistry 1994, 33, 3494-3500.
22. G. Caron, G. W.-M. Tseng, R. J. Kazlauskas, "Kinetic Resolutions Concentrate the Minor Enantiomer and Aid Measurement of High Enantiomeric Purity" Tetrahedron: Asymmetry 1994, 5, 83-92.
21. G. Caron, R. J. Kazlauskas, "Sequential Kinetic Resolution of (±)-2,3-Butanediol Using Lipase from Pseudomonas cepacia" Tetrahedron: Asymmetry 1993, 4, 1995-2000.
20. R. J. Kazlauskas, "Biocatalysis - Becoming More Predictable and Selective" Trends Biotechnol. 1993, 11, 439-440.
19. A. K. Gupta, R. J. Kazlauskas, "Substrate Modification to Increase the Enantioselectivity of Hydrolases. A Route to Optically-Active Cyclic Allylic Alcohols" Tetrahedron: Asymmetry 1993, 4, 879-888.
18. I. J. Colton, R. J. Kazlauskas, "Synthesis of an Acyl Phosphate Driven by a Proton Gradient. A Model for H+-ATPase" J. Org. Chem. 1992, 57, 7005-7006.
17. A. K. Gupta, R. J. Kazlauskas, "Calibration Plots to Aid Determination of High Enantiomeric Purity Using Chiral Lanthanide Shift Reagents" Tetrahedron: Asymmetry 1991, 3, 243-246.
16. G. Caron, R. J. Kazlauskas, "An Optimized Sequential Kinetic Resolution of trans-1,2-Cyclohexanediol" J. Org. Chem. 1991, 56, 7251-7256.
15. R. J. Kazlauskas, "(S)-(-)- and (R)-(+)-1,1'-Bi-2-naphthol" Org. Synth. 1991, 70, 60-67; Org. Synth., Coll. Vol. IX, 1998, 77-84. pdf
14. R. J. Kazlauskas, A. N. E. Weissfloch, A. T. Rappaport, L. A. Cuccia, "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.
13. R. J. Kazlauskas, "Resolution of binaphthols and spirobiindanols using pancreas extracts" in Biocatalysis, Abramowicz, D. A., Ed.; Van Nostrand Reinhold: New York; 1990; pp 195-216.From General Electric Company
12. R. J. Kazlauskas, "Resolution of binaphthols and spirobiindanols using cholesterol esterase" J. Am. Chem. Soc. 1989, 111, 4953-4959.
11. R. J. Kazlauskas, "Changing coenzymes improves oxidations catalyzed by alcohol dehydrogenase" J. Org. Chem. 1988, 53, 4633-4635.
10. R. J. Kazlauskas, "Preparation of 4-nitrophthalic anhydride from N-methyl-4-nitrophthalimide," Org. Prep. Proc. Int. 1988, 20, 423-425.
Patents 5. A. Cimpoia, L. Janes, R. Kazlauskas, “Stereoselective synthesis of nucleoside analogues” PCT Int. Appl. 2000, WO 0047759 A1 20000817.
4. L. E. Janes, A. C. Löwendahl, R. J. Kazlauskas, “pH-Indicator based assay for stereoselective enzymes” PCT Int. Appl. 1999, WO 9967420 A1 19991229.
3. R. J. Kazlauskas, X. Zhang, “Method for Preparing Optically-Active 5-Hydroxy-3-(4’-hydroxyphenyl)-1,1,3-trimethylindane” U.S. Patent 5,959,159; 1999.

Kazlauskas Group Publications
back	2009 95. T. Yin, P. Bernhardt, K.L. Morley, Y. Jiang, J.D. Cheeseman, V. Purpero, J.D. Schrag, R.J. Kazlauskas “Switching catalysis from hydrolysis to perhydrolysis in P. fluorescens esterase” 2009, submitted. 94. S.K. Padhi, R Fujii, G.A. Legatt, S.L. Fossum, R. Berchtold, R.J. Kazlauskas "Switching from an esterase mechanism to a hydroxynitrile lyase mechanism requires only two amino acid substitutions" 2009, submitted. 93. J.-H. Park, H.-J. Ha, W. K. Lee, T. Généreux-Vincent, R. J. Kazlauskas "Molecular basis for the stereoselective ammoniolysis of N-alkyl aziridine-2-carboxylates catalyzed by Candida antarctica lipase B" ChemBioChem 2009, 10, accepted. 92. R. J. Kazlauskas, U. T. Bornscheuer "Finding better protein engineering strategies" Nature Chem. Biol. 2009, 5, 526-529. more... 91. S. Duncan, Q. Jing, A. Katona, R. J. Kazlauskas, J. Schilling, U. Tschirner, W. Wafa AlDajani “Increased saccharification yields from aspen biomass upon treatment with enzymatically generated peracetic acid." Appl. Biochem. Biotechnol. 2009, in press. more... 90. H. Jochens, K. Stiba, C. Savile, R. Fujii, J.-G. Yu, T. Gerassenkov, R. J. Kazlauskas, U. T. Bornscheuer “Converting an esterase into an epoxide hydrolase” Angew. Chem. Intl. Ed. 2009, 48, 3532-3535. more... 89. Q. Jing, K. Okrasa, R. J. Kazlauskas "Stereoselective hydrogenation of olefins using rhodium-substituted carbonic anhydrase – a new reductase" Chem. Eur. J. 2009, 15, 1370-1376. more... 88. Qing Jing, Krzysztof Okrasa, Romas J. Kazlauskas “Manganese-substituted a-carbonic anhydrase as an enantioselective peroxidase” Topics Organometall. Chem. 2009, 25, 45-61. more... 2008 87. P. Mugford, U. Wagner, Y. Jiang, K. Faber, R. Kazlauskas “Enantiocomplementary enzymes: Classification, molecular basis for their reversed enantiopreference and prospects for mirror-image biotransformations” Angew. Chem. Intl. Ed. 2008, 47, 8782-8793. more... 86. J.T. Gorke, F. Srienc, R.J. Kazlauskas “ Enzymatic biotransformations in deep eutectic solvents" Chem. Commun. 2008, 1235-1237. more... 85. Q. Jing, R.J. Kazlauskas "Determination of absolute configurations of secondary alcohols by lipase-catalyzed kinetic resolutions" Chirality, 2008, 20, 724-735. more... 2007 84. J.T. Gorke, K. Okrasa, A. Louwagie, R.J. Kazlauskas, F. Srienc “ Enzymatic synthesis of poly(hydroxyalkanoates) in ionic liquids” J. Biotechnol. 2007, 132, 306-313. more... 2006 83. R.J. Kazlauskas, "News & Views: Engineering a multipurpose catalyst" Nature Chem. Biol. 2006, 2, 514-515. more... 82. C.K. Savile, R.J. Kazlauskas, “The 3-(3-pyridine)propionyl anchor group for protease-catalyzed resolutions: p-toluenesulfinamide and sterically hindered secondary alcohols” Adv. Synth. Catal. 2006, 348, 1183-1192. more... 81. K. Okrasa, R.J. Kazlauskas, “Manganese carbonic anhydrase as an enantioselective epoxidation of olefins with hydrogen peroxide” Chem. Eur. J. 2006, 11, 1587-1596. more... 80. I. Lavandera, S. Fernández, J. Magdalena, M. Ferrero, C.K. Savile, H. Grewal, R.J. Kazlauskas, V. Gotor, “Molecular basis for the unusual regioselectivity of lipase from Pseudomonas cepacia toward the secondary alcohol of 2’-deoxynucleosides” ChemBioChem, 2006, 7, 1381-1390. more... 79. A. Nisole , F.-X. Lussier, K.L. Morley, F. Shareck, R.J. Kazlauskas, C. Dupont, J.N. Pelletier “Secretion of Streptomyces lividans acetylxylan esterase A in Escherichia coli for rapid detection of activity” Prot. Express. Purif. 2006, 46, 274-284. more... 78. K.L. Morley, G. Chauve, R.J. Kazlauskas, C. Dupont, F. Shareck, R.H. Marchessault, “Acetyl xylan esterase activity on chitin and chitosan substrates” Carbohydr. Polym. 2006, 63, 310-315. more... 2005 77. U.T. Bornscheuer, R.J. Kazlauskas, Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations, 2nd edition, Wiley-VCH: Weinheim, 2005. more... 76. R.J. Kazlauskas, “Quantitative assay of hydrolases for activity and selectivity using color changes” in Enzyme Assays: High-throughput Screening, Genetic Selection and Fingerprinting, J.-L. Reymond, Ed., Wiley-VCH: Weinheim, 2005, 17-39. more... 75. R.J. Kazlauskas "News & Views: Biological Chemistry: Enzymes in Focus" Nature 2005, 436, 1096-1097. more... 74. C.K. Savile, R.J. Kazlauskas “How substrate solvation contributes to the enantioselectivity of subtilisin toward secondary alcohols” J. Am. Chem. Soc. 2005, 127, 12228-12229. more... 73. P.F. Mugford, V.P. Magloire, R.J. Kazlauskas, “Unexpected subtilisin-catalyzed hydrolysis of a sulfinamide bond in preference to a carboxamide bond in N-acyl sulfinamides” J. Am. Chem. Soc. 2005, 127, 6536-6537. more... 72. P. Bernhardt, K. Hult, R.J. Kazlauskas, “Molecular basis for perhydrolase activity in a/b hydrolases” Angew. Chem. Intl. Ed. 2005, 44, 2742-2746. more... 71. R.J. Kazlauskas, “Enhancing catalytic promiscuity for biocatalysis” Curr. Opin. Chem. Biol. 2005, 9, 195-201. more... 70. K.L. Morley, R. J. Kazlauskas, “Improving enzyme properties: when are closer mutations better?” Trends Biotechnol. 2005, 23, 231-237. more... 69. I. Lavandera, S. Fernández, J. Magdalena, M. Ferrero, R.J. Kazlauskas, V. Gotor,, “An inverse substrate orientation for the regioselective acylation of 3',5'-diaminonucleosides catalyzed by Candida antarctica lipase B?” ChemBioChem 2005, 6, 1381-1390. more... 68. A. Mezzetti, J. Schrag, C.S. Cheong, R.J. Kazlauskas, “Mirror-image packing in enantiomer discrimination: Molecular basis for the enantioselectivity of Burkholderia cepacia lipase toward 2-methyl-3-phenyl-1-propanol” Chem. Biol. 2005, 12, 427-437. more... 67. C.K. Savile, V.P. Magloire, R.J. Kazlauskas, “Subtilisin-catalyzed resolution of N-acyl arylsulfinamides” J. Am. Chem. Soc. 2005, 127, 2104-2113. more... 66. S. Park, K. Morley, G.P. Horsman, M. Holmquist, K. Hult, R.J. Kazlauskas, “Focusing mutations into the P. fluorescens esterase binding site increases enantioselectivity more effectively than random mutagenesis” Chem. Biol., 2005, 12, 45-54. more... 65. J.D. Cheeseman, A.D. Corbett, J.L. Gleason, R.J. Kazlauskas, “Receptor-assisted combinatorial chemistry: thermodynamics and kinetics in drug discovery” Chem. Eur. J. 2005, 10, 1708-1716. more... 2004 64. K. L. Morley, V. P. Magloire, C. Guerard, R. J. Kazlauskas, “Parallel synthesis of esters by solution-phase acylation of alcohols with acid chlorides using solid-supported reagents to eliminate traditional purification” Tetrahedron: Asymmetry 2004, 15, 3005-3009. more... 63. U. T. Bornscheuer, R. J. Kazlauskas, “Catalytic promiscuity in biocatalysis: using old enzymes to form new bonds and follow new pathways” Angew. Chem. Intl. Ed. 2004, 43, 6032-6040. more... 62. N. Somers, R.J. Kazlauskas, "Mapping the substrate selectivity and enantioselectivity of esterases from thermophiles" Tetrahedron: Asymmetry, 2004, 15, 2991-3004. more... 61. J.D. Cheeseman, A. Tocilj, J.D. Schrag, R.J. Kazlauskas, “X-Ray crystal structure of an aryl esterase from Pseudomonas fluorescens” Acta Crystallogr. D 2004, D60, 1237-1243. more ... [July 2004 cover picture] 60. P.F. Mugford, S.M. Lait, B.A. Keay, R.J. Kazlauskas, “Enantiocomplementary enzymatic resolution of the chiral auxiliary cis,cis-6-(2,2-dimethylpropanamido)spiro[4.4]-nonan-1-ol and the molecular basis for the high enantioselectivity of subtilisin Carlsberg” ChemBioChem, 2004, 5, 980-987. more ... 59. A.D. Corbett, J.D. Cheeseman, R.J. Kazlauskas, J.L. Gleason, “Pseudo-dynamic combinatorial libraries: a new receptor-assisted approach for drug discovery” Angew. Chem. Intl. Ed. 2004, 43, 2432-2436. more ... Flagged by the reviewers as a ‘very important paper’. 2003 58. A. Mezzetti, C. Keith, R.J. Kazlauskas, “Highly enantioselective kinetic resolution of primary alcohols of the type Ph-X-CH(CH3)CH2OH by Pseudomonas cepacia lipase. Effect of acyl chain length and solvent” Tetrahedron: Asymmetry 2003, 14, 3917-3924. more ... 57. S. Park, F. Viklund, R. J. Kazlauskas, K. Hult “Vacuum-driven lipase-catalyzed direct condensation of L-ascorbic acid and fatty acids in ionic liquids: synthesis of natural surface-active antioxidants” Green Chem. 2003, 5, 715-719. more ... 56. S. Park, R. J. Kazlauskas “Biocatalysis in ionic liquids – advantages beyond green technology” Curr. Opin. Biotechnol. 2003, 14, 432-437. more ... 55. S. Park, E. Forró, H. Grewal, F. Fülöp, R.J. Kazlauskas “Molecular basis for the enantioselective ring opening of b-lactams catalyzed by Candida antarctica lipase B” Adv. Synth. Catal. 2003, 345, 986-995. more... 54. G.P. Horsman, A.M.F. Liu, E. Henke, U.T. Bornscheuer, R.J. Kazlauskas “Mutations in distant residues moderately increase the enantioselectivity of Pseudomonas fluorescens esterase toward methyl 3-bromo-2-methylpropanoate and ethyl 3-phenylbutyrate” Chem. Eur. J. 2003, 9, 1933-1939. more... 53. “Ionic liquids create new opportunities for nonaqueous biocatalysis: acylation of glucose and ascorbic Acid” in Ionic Liquids in Green Chemistry, Prospects and Opportunities, Rogers, R.D.; Seddon, K.R., Eds., ACS Symposium Series, 2003, 856, 225-238. 2002 52. J.D. Cheeseman, A.D. Corbett, R. Shu, J. Croteau, J.L. Gleason, R.J. Kazlauskas “Amplification of screening sensitivity through selective destruction: theory and screening of a library of carbonic anhydrase inhibitors” J. Am. Chem. Soc. 2002, 124, 5692-5701. more ... (Highlighted in Nature Rev. Drug Discov. 2002, 1, 412; Curr. Opin. Chem. Biol. 2002, 6, 407-408; Canadian Chem. News 2002, Sept. pp. 19-20; chosen as a key paper on the ‘Faculty of 1000’ website) 2001 51. R.J. Kazlauskas, “Modeling - a tool for experimentalists” Science, 2001, 293, 2277-2279. more ... (invited Tech.Sight essay about molecular modeling) 50. S. Park, R. J. Kazlauskas, “Improved preparation and use of room temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations, J. Org.Chem. 2001, 66, 8395-8401. more ... 49. D.G. Gascoyne, H.L. Finkbeiner, K.P. Chan, J.L. Gordon, K.R. Stewart, R.J. Kazlauskas “Molecular basis for enantioselectivity of lipase from Chromobacterium viscosum toward the dibutanoate ester of 2,3-dihydro-3-(4’-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol” J. Org. Chem., 2001, 66, 3041-3048. more... 48. A. Man Fai Liu, N.A. Somers, R. J. Kazlauskas, T.S. Brush, F. Zocher, M. Enzelberger, U.T. Bornscheuer, G.P. Horsman, A. Mezzetti, C. Schmidt-Dannert, R.D. Schmid, “Mapping the substrate selectivity of new hydrolases using colorimetric screening: lipases from Bacillus thermocatenulatus and Ophiostoma piliferum, esterases from Pseudomonas fluorescens and Streptomyces diastatochromogenes” Tetrahedron: Asymmetry 2001, 12, 545-556. more ... 47. A.N.E. Weissfloch, R.J. Kazlauskas, “Choosing Hydrolases for Enantioselective Reactions Involving Alcohols Using Empirical Rules” in Methods in Biotechnology, Vol 15: Enzymes in Nonaqueous Solvents: Methods and Protocols, E.N. Vulfson, P.J. Halling, H.L. Holland, Eds., Humana Press: Totowa, NJ, 2001, 243-259. 2000 46. R.J. Kazlauskas, "Molecular modeling and biocatalysis – explanations, predictions, limitations, and opportunities" Curr. Opin. Chem. Biol. 2000, 4, 81-88. more ... 45. A.N.E. Weissfloch, R.J. Kazlauskas, "Molecular basis for empirical rules that predict the stereoselectivity of hydrolases" in Enzymes in Action: Green Solutions for Chemical Problems, Zwannenburg, B., Mikolajczyk, M., Kielbasinski, P., Eds., NATO Science Series, Kluwer Academic: Dordrecht, 2000, pp. 43-69. before 2000 44. L.E. Janes, A. Cimpoia, R.J. Kazlauskas, “Protease-mediated separation of cis and trans diastereomers of 2-(R,S)-benzyloxymethyl-4-(S)-carboxylic acid-1,3-dioxolane methyl ester: intermediates for the synthesis of dioxolane nucleosides” J. Org. Chem. 1999, 64, 9019-9029. more... 43. M. Zhang, R. Kazlauskas, "First preparation of enantiopure indane monomer, (S)-(–)- and (R)-(+)-2,3-dihydro-3-(4’-hydroxyphenyl)-1,1,3-trimethyl-1H-inden-5-ol, via a unique enantio- and regioselective enzymatic kinetic resolution" J. Org. Chem. 1999, 64, 7498-7503. 42. H.K. Weber, H. Weber, R.J. Kazlauskas, "’Watching’ lipase-catalyzed acylations using 1H-NMR: competing hydrolysis of vinyl acetate in dry organic solvents." Tetrahedron: Asymmetry 1999, 10, 2635-2638. 41. W.V. Tuomi, R.J. Kazlauskas, "Molecular basis for enantioselectivity of lipase from Pseudomonas cepacia toward primary alcohols. Modeling, kinetics and chemical modification of Tyr29 to increase or decrease enantioselectivity" J. Org. Chem. 1999, 64, 2638-2647. Book: Uwe T. Bornscheuer, Romas J. Kazlauskas Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations Wiley-VCH: Weinheim, 1999. 40. R. J. Kazlauskas, U. T. Bornscheuer “Biotransformations with Lipases” Biotechnology, 2nd ed., Vol. 8a Biotransformations I, David R. Kelly, Ed. VCH: Weinheim, 1998, 37-191. 39. R. J. Kazlauskas, H. K. Weber "Improving hydrolases for organic synthesis" Curr. Opin. Chem. Biol., 1998, 2, 121-126. 38. L. E. Janes, A. C. Löwendahl, R. J. Kazlauskas, “Rapid quantitative screening of hydrolases using pH indicators. Finding enantioselective hydrolases.” Chem. Eur. J. 1998, 4, 2324-2331. 37. L. E. Janes, R. J. Kazlauskas, "Empirical rules for the enantiopreference of lipase from Aspergillus niger toward secondary alcohols and carboxylic acids, especially a-amino acids" Tetrahedron: Asymmetry 1997, 8, 3719-3734. 36. L. E. Janes, R. J. Kazlauskas, "Quick E. A Fast Spectrophotometric Method to Measure the Enantioselectivity of Hydrolases" J. Org. Chem. 1997, 62, 4560-4561. 35. R. J. Kazlauskas, A. N. E. Weissfloch “A Structure-Based Rationalization of the Enantiopreference of Subtilisin toward Secondary Alcohols and Isosteric Primary Amines” J. Mol. Catal. B Enz. 1997, 3, 65-72. 34. G. A. R. Nobes, R. J. Kazlauskas, R. H. Marchessault, "Lipase-Catalyzed Ring Opening Polymerization of Lactones: A Novel Route to Poly(hydroxyalkanoates)." Macromolecules 1996, 29, 4829-4833. 33. A. N. E. Weissfloch, R. J. Kazlauskas, "Enantiopreference of Lipase From Pseudomonas Cepacia toward Primary Alcohols" J. Org. Chem. 1995, 60, 6959-6969. 32. A. N. Serreqi, R. J. Kazlauskas, "Kinetic Resolution of Sulfoxides Catalyzed by Cholesterol Esterase: Substrate Mapping and an Empirical Rule" Can. J. Chem. 1995, 73, 1357-1367. 31. I. J. Colton, S. N. Ahmed, R. J. Kazlauskas, "Isopropanol Treatment Increases Enantioselectivity of Candida rugosa Lipase toward Carboxylic Acid Esters" J. Org. Chem. 1995, 60, 212-217. 30. A. N. Serreqi, R. J. Kazlauskas, "Kinetic Resolution of Phosphines and Phosphine Oxides Catalyzed by Hydrolases" J. Org. Chem. 1994, 59, 7609-7615. 29. I. J. Colton, R. J. Kazlauskas, "Dicarboxylic Acids Link Proton Transfer across a Liq-uid Membrane to the Synthesis of an Acyl Phosphate. A Model for P-type H+-ATPase." J. Org. Chem. 1994, 59, 3626-3635. 28. G. Caron, R. J. Kazlauskas, "Isolation of Racemic 2,4-Pentanediol and 2,5-Hexanediol from Commercial Mixtures of Meso and Racemic Isomers by way of Cyclic Sulfites." Tetrahedron: Asymmetry 1994, 5, 657-664. 27. S. N. Ahmed, R. J. Kazlauskas, A. H. Morinville, P. Grochulski, J. D. Schrag, M. Cygler, "Enantioselectivity of Candida Rugosa Lipase toward Carboxylic Acids: A Predictive Rule from Substrate Mapping and X-Ray Crystallography" Biocatalysis, 1994, 9, 209-225. 26. M. C. Ng-Youn-Chen, A. N. Serreqi, Q. Huang, R. J. Kazlauskas, "Ki-netic Resolution of Pipecolic Acid Using Partially-Purified Lipase from Aspergillus niger" J. Org. Chem. 1994, 59, 2075-2081. 25. R. J. Kazlauskas, "Elucidating Structure-Mechanism Relationships in Lipases: Prospects for Predicting and Engineering Catalytic Properties" Trends Biotechnol. 1994, 12, 464-472; Erratum, 1995, 13, 195. 24. M. Cygler, P. Grochulski, R. J. Kazlauskas, J. D. Schrag, F. Bouthillier, B. Rubin, A. N. Serreqi, A. K. Gupta, "Molecular Basis for the Enantiopreference of Lipases toward Secondary Alcohols" J. Am. Chem. Soc. 1994, 116, 3180-3186. [Highlighted in Nature Structural Biology 1994, 1, 569-72.] 23. P. Grochulski, F. Bouthillier, R. J. Kazlauskas, A. N. Serreqi, J. D. Schrag, E. Ziomek, M. Cygler, "Candida rugosa Lipase-Inhibitor Complexes Simulating the Acylation and Deacylation Transition States" Biochemistry 1994, 33, 3494-3500. 22. G. Caron, G. W.-M. Tseng, R. J. Kazlauskas, "Kinetic Resolutions Concentrate the Minor Enantiomer and Aid Measurement of High Enantiomeric Purity" Tetrahedron: Asymmetry 1994, 5, 83-92. 21. G. Caron, R. J. Kazlauskas, "Sequential Kinetic Resolution of (±)-2,3-Butanediol Using Lipase from Pseudomonas cepacia" Tetrahedron: Asymmetry 1993, 4, 1995-2000. 20. R. J. Kazlauskas, "Biocatalysis - Becoming More Predictable and Selective" Trends Biotechnol. 1993, 11, 439-440. 19. A. K. Gupta, R. J. Kazlauskas, "Substrate Modification to Increase the Enantioselectivity of Hydrolases. A Route to Optically-Active Cyclic Allylic Alcohols" Tetrahedron: Asymmetry 1993, 4, 879-888. 18. I. J. Colton, R. J. Kazlauskas, "Synthesis of an Acyl Phosphate Driven by a Proton Gradient. A Model for H+-ATPase" J. Org. Chem. 1992, 57, 7005-7006. 17. A. K. Gupta, R. J. Kazlauskas, "Calibration Plots to Aid Determination of High Enantiomeric Purity Using Chiral Lanthanide Shift Reagents" Tetrahedron: Asymmetry 1991, 3, 243-246. 16. G. Caron, R. J. Kazlauskas, "An Optimized Sequential Kinetic Resolution of trans-1,2-Cyclohexanediol" J. Org. Chem. 1991, 56, 7251-7256. 15. R. J. Kazlauskas, "(S)-(-)- and (R)-(+)-1,1'-Bi-2-naphthol" Org. Synth. 1991, 70, 60-67; Org. Synth., Coll. Vol. IX, 1998, 77-84. pdf 14. R. J. Kazlauskas, A. N. E. Weissfloch, A. T. Rappaport, L. A. Cuccia, "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. 13. R. J. Kazlauskas, "Resolution of binaphthols and spirobiindanols using pancreas extracts" in Biocatalysis, Abramowicz, D. A., Ed.; Van Nostrand Reinhold: New York; 1990; pp 195-216.From General Electric Company 12. R. J. Kazlauskas, "Resolution of binaphthols and spirobiindanols using cholesterol esterase" J. Am. Chem. Soc. 1989, 111, 4953-4959. 11. R. J. Kazlauskas, "Changing coenzymes improves oxidations catalyzed by alcohol dehydrogenase" J. Org. Chem. 1988, 53, 4633-4635. 10. R. J. Kazlauskas, "Preparation of 4-nitrophthalic anhydride from N-methyl-4-nitrophthalimide," Org. Prep. Proc. Int. 1988, 20, 423-425. Patents 5. A. Cimpoia, L. Janes, R. Kazlauskas, “Stereoselective synthesis of nucleoside analogues” PCT Int. Appl. 2000, WO 0047759 A1 20000817. 4. L. E. Janes, A. C. Löwendahl, R. J. Kazlauskas, “pH-Indicator based assay for stereoselective enzymes” PCT Int. Appl. 1999, WO 9967420 A1 19991229. 3. R. J. Kazlauskas, X. Zhang, “Method for Preparing Optically-Active 5-Hydroxy-3-(4’-hydroxyphenyl)-1,1,3-trimethylindane” U.S. Patent 5,959,159; 1999.

Kazlauskas Group Publications