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Original Article

Problems of Acyl Migration in Lipase-Catalyzed Enantioselecttve Transformation of Meso-1,3-Diol Systems

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Pages 169-177 | Received 29 Mar 1989, Published online: 11 Jul 2009

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Anna Millqvist Fureby, Carmen Virto, Patrick Adlercreutz & Bo Mattiasson. (1996) Acyl Group Migrations in 2-Monoolein. Biocatalysis and Biotransformation 14:2, pages 89-111.
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S. Bornemann, J. M. Cassells, J. S. Dordick & A. J. Hacking. (1992) The Use of Enzymes to Regioselectively Deacylate Sucrose Esters. Biocatalysis 7:1, pages 1-12.
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Barry M. Trost, Sushant Malhotra, Takashi Mino & Naomi S. Rajapaksa. (2008) Dinuclear Zinc‐Catalyzed Asymmetric Desymmetrization of Acyclic 2‐Substituted‐1,3‐Propanediols: A Powerful Entry into Chiral Building Blocks. Chemistry – A European Journal 14:25, pages 7648-7657.
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Enzo Santaniello, Silvana Casati, Pierangela Ciuffreda & Luca Gamberoni. (2004) Asymmetrization of 2-methylpropane-1,3-diol by Mucor miehei lipase-catalyzed benzoylation in organic solvent. Tetrahedron: Asymmetry 15:20, pages 3177-3179.
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Michaela Edin & Jan-E. Bäckvall. (2003) On the Mechanism of the Unexpected Facile Formation of m eso -Diacetate Products in Enzymatic Acetylation of Alkanediols . The Journal of Organic Chemistry 68:6, pages 2216-2222.
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Marielle Lemaire & Jean Bolte. (1999) Enzymatic resolution of a 1,2-cyclic sulphite glycerol derivative. Tetrahedron: Asymmetry 10:24, pages 4755-4762.
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Shrivallabh B. Desai, Narshinha P. Argade & Krishna N. Ganesh. (1999) Selectivity Paradigm in Lipase Reactions:  Correlating Actual and Observed Regioselectivity in Hydrolysis of Unsymmetrical Diacetates. The Journal of Organic Chemistry 64:22, pages 8105-8107.
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B. Anders Persson, Fernando F. Huerta & Jan-E. Bäckvall. (1999) Dynamic Kinetic Resolution of Secondary Diols via Coupled Ruthenium and Enzyme Catalysis. The Journal of Organic Chemistry 64:14, pages 5237-5240.
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Romas J. Kazlauskas & Uwe T. Bornscheuer. 1998. Biotechnology. Biotechnology 36 191 .
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Charmian J. O'Connor & Richard H. Barton. (1997) Modifications of emulsions for determination of the rates of lipase-catalysed hydrolysis and intramolecular acyl transfer reactions of lipids. Journal of Molecular Liquids 72:1-3, pages 263-277.
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Andrea Kovac, Peter Stadler, Lutz Haalck, Fritz Spener & Fritz Paltauf. (1996) Hydrolysis and esterification of acylglycerols and analogs in aqueous medium catalyzed by microbial lipases. Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism 1301:1-2, pages 57-66.
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Kwo-Feng Hsiao, Fang-Lin Yang, Shih-Hsiung Wu & Kung-Tsung Wang. (1995) Effects of acyl groups and ethanol ratios on lipase-catalyzed regioselective deacylation in peracylated methyl glycopyranosides. Biotechnology Letters 17:9, pages 963-968.
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Hanna S.H. Gautun & Per H.J. Carlsen. (1995) Nucleophilic ring opening of cyclic sulphamidites. Tetrahedron: Asymmetry 6:7, pages 1667-1674.
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Uwe T. Bornscheuer. (1995) Lipase-catalyzed syntheses of monoacylglycerols. Enzyme and Microbial Technology 17:7, pages 578-586.
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U. Bornscheuer. (2006) Lipase‐katalysierte Synthese von Monoglyceriden. Lipid / Fett 97:7-8, pages 241-249.
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Fritz Theil. (1994) Diols as substrates in lipase-catalyzed enantioselective acylations - a brief review. Catalysis Today 22:3, pages 517-536.
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Philip E. Sonnet & Robert L. Dudley. (1994) Stereospecific synthesis of selected triglycerides: comments on acyl migration and analysis of configuration. Chemistry and Physics of Lipids 72:2, pages 185-191.
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Kwo-Feng-Hsiao, Hsuen-Ju Lin, De-Ling Leu, Shih-Hsiung Wu & Kung-Tsung Wang. (1994) Kinetic study of deacetylation and acetyl migration of peracetylated 1-methyl α,β-D-glcopyranosides by Candida lipase-catalyzed hydrolysis. Bioorganic & Medicinal Chemistry Letters 4:13, pages 1629-1632.
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Monique-Agnès Mbappé & Sames Sicsic. (1993) Enzymatic resolutions in 3-amino-1,2-propanediol series. Tetrahedron: Asymmetry 4:5, pages 1035-1040.
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Bernardo Herradón, Sénida Cueto, Anabel Morcuende & Serafín Valverde. (1993) Regio- and enantioselective esterifications of polyoxygenated compounds catalyzed by lipases. Tetrahedron: Asymmetry 4:5, pages 845-864.
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Enzo Santaniello, Patrizia Ferraboschi & Paride Grisenti. (1993) Lipase-catalyzed transesterification in organic solvents: Applications to the preparation of enantiomerically pure compounds. Enzyme and Microbial Technology 15:5, pages 367-382.
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Pawinee Kanasawud, Suree Phutrakul, Scott Bloomer, Patrick Adlercreutz & Bo Mattiasson. (1992) Triglyceride interesterification by lipases. 3. Alcoholysis of pure triglycerides. Enzyme and Microbial Technology 14:12, pages 959-965.
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Paride Grisenti, Patrizia Ferraboschi, Ada Manzocchi & Enzo Santaniello. (1992) Enantioselective transesterification of 2-methyl-1,3-propanediol derivatives catalyzed by Pseudomonas fluorescens lipase in an organic solvent. Tetrahedron 48:18, pages 3827-3834.
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