1.3. 1 Resolution of Alcohols, Acids, and Esters by Hydrolysis
Book
Editors: Faber, K.; Fessner, W.-D.; Turner, N. J.
Title: Biocatalysis in Organic Synthesis 1
Print ISBN: 9783131741318; Online ISBN: 9783131975218; Book DOI: 10.1055/b-003-125815
1st edition © 2015. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry
Science of Synthesis Reference Libraries
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Type: Multivolume Edition
Abstract
This chapter reviews the use of enzymes, principally esterases and lipases, as catalysts for the resolution of racemic carboxylic acid derivatives via hydrolysis. The resolution of esters of chiral primary, secondary, and tertiary alcohols, as well as diols, are examined. Biocatalytic hydrolytic methods for the desymmetrization of prochiral substrates and meso-compounds are also considered.
Key words
carboxylic acids - carboxylic esters - alcohols - diols - resolution - esterase - lipase - hydrolysis - meso-trick - desymmetrization - dynamic kinetic resolution - substrate engineering - substrate design- 5 Ogawa J, Ryono A, Xie S.-X, Vohra RM, Indrati R, Akamatsu M, Miyagawa H, Ueno T, Shimizu S. J. Mol. Catal. B: Enzym. 2001; 12: 71
- 7 van Hylckama Vlieg JET, Tang L, Lutje Spelberg JH, Smilda T, Poelarends GJ, Bosma T, van Merode AEJ, Fraaije MW, Janssen DB. J. Bacteriol. 2001; 183: 5058
- 10 Arisawa A, Matsufuji M, Nakashima T, Dobashi K, Isshiki K, Yoshioka T, Yamada S, Momose H, Taguchi S. Appl. Environ. Microbiol. 2002; 68: 2716
- 15 Jeromin GE, Bertau M. Bioorganikum: Praktikum der Biotransformationen. Wiley-VCH; Weinheim, Germany 2005
- 18 Miled N, Beisson F, de Caro J, de Caro A, Arondel V, Verger R. J. Mol. Catal. B: Enzym. 2001; 11: 165
- 51 Lagarde D, Nguyen H.-K, Ravot G, Wahler D, Reymond J.-L, Hills G, Veit T, Lefevre F. Org. Process Res. Dev. 2002; 6: 441
- 55 Bornscheuer UT, Kazlauskas RJ. Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations. Wiley-VCH; Weinheim, Germany 2006
- 56 Cardenas F, Alvarez E, de Castro-Alvarez M.-S, Sanchez-Montero J.-M, Valmaseda M, Elson SW, Sinisterra J.-V. J. Mol. Catal. B: Enzym. 2001; 14: 111
- 58 Cotterill IC, Sutherland AG, Roberts SM, Grobbauer R, Spreitz J, Faber K. J. Chem. Soc., Perkin Trans. 1 1991; 1365
- 60 Lalonde JJ, Govardhan C, Khalaf N, Martínez AG, Visuri K, Margolin AL. J. Am. Chem. Soc. 1995; 117: 6845
- 66 Hobson AH, Buckley CM, Aamand JL, Jørgenson ST, Diderichsen B, McConnell DJ. Proc. Natl. Acad. Sci. U. S. A. 1993; 90: 5682
- 67 Stewart JE, Feinle-Bisset C, Golding M, Delahunty C, Clifton PM, Keast RSJ. Br. J. Nutr. 2010; 104: 145
- 68 Vulfson EN, Lipases: their structure, biochemistry and application Wooley P, Petersen SB. Cambridge University Press Cambridge 1994; 271–288
- 69 Haas MJ, Joerger RD, Food Biotechnology Hui YH, Khachatourians GG. Wiley-VCH Weinheim, Germany 1995; 549–588
- 71 Berry DR, Paterson A, Enzyme Chemistry: Impact and Applications Suckling CJ. Chapman and Hall London 1990; 306
- 72 Kazlauskas RJ, Bornscheuer UT, Biotechnology Rehm H.-J, Reed G. Wiley-VCH Weinheim, Germany 1998; 8a. 37–191
- 77 Liese A, Seelbach K, Buchholz A, Haberland J, Industrial Biotransformations Liese A, Seelbach K, Wandrey C. Wiley-VCH Weinheim, Germany 2006; 273–349
- 78 MacKeith RA, McCague R, Olivo HF, Roberts SM, Taylor SJC, Xiong H. Bioorg. Med. Chem. 1994; 2: 387
- 79 McConville FX, Lopez JL, Wald SA, Biocatalysis Abramowicz DA. Springer Dordrecht, The Netherlands 1990; 167
- 83 Ingold CK. Structure and Mechanism in Organic Chemistry. Cornell University Press; Ithaca, NY 1969
- 125 Theurer M, Fischer P, Baro A, Nguyen G.-S, Kourist R, Bornscheuer U, Laschat S. Tetrahedron 2010; 66: 3814
- 128 Wiggers M, Holt J, Kourist R, Bartsch S, Arends IWCE, Minnaard AJ, Bornscheuer UT, Hanefeld U. J. Mol. Catal. B: Enzym. 2009; 60: 82
- 129 Bassegoda A, Nguyen G.-S, Schmidt M, Kourist R, Diaz P, Bornscheuer UT. ChemCatChem 2010; 2: 962
- 130 Nguyen G.-S, Kourist R, Paravidino M, Hummel A, Rehdorf J, Orru RVA, Hanefeld U, Bornscheuer UT. Eur. J. Org. Chem. 2010; 2753
- 139 Ramos Tombo GM, Schär H.-P, Fernandez i Busquets X, Ghisalba O. Tetrahedron Lett. 1986; 27: 5707
- 144 Patel RN, Banerjee A, Pendri YR, Liang J, Chen C.-P, Mueller R. Tetrahedron: Asymmetry 2006; 17: 175
- 150 Rozeboom HJ, Godinho LF, Nardini M, Quax WJ, Dijkstra BW. Biochim. Biophys. Acta, Proteins Proteomics 2014; 1844: 567