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Resolution of 2-methylalkanoic acids. Enantioselective esterification with long chain alcohols catalysed by Candida rugosa lipase
Mid Sweden University.ORCID iD: 0000-0002-9577-832X
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1996 (English)In: Acta Chemica Scandinavica, ISSN 0904213X (ISSN), Vol. 50, no 8, 666-671 p.Article in journal (Refereed) Published
Abstract [en]

Candida rugosa lipase catalysed resolutions of 2-methylalkanoic acids run on a large scale often display decreased enantiomeric rations (E-values) and reaction rates compared with small-scale experiments. By continuous control of the water activity (addition of inorganic salt/hydrated salt mixtures) this can be avoided. The importance of the proper choice of alcohol as well as its concentration is demonstrated. (R)-2-Methyloctanoic acid (8.6g) and (S)-2-methyl-1-octanol (4.5 g), both in 99.6% ee were prepared from 20 g racemic 2-methyloctanoic acid. © Acta Chemica Scandinavica 1996.

Place, publisher, year, edition, pages
1996. Vol. 50, no 8, 666-671 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-74871OAI: oai:DiVA.org:kth-74871DiVA: diva2:490140
Note
References: Sheldon, R.A., (1993) Chirotechnology, Industrial Synthesis of Optically Active Compounds, , Marcel Dekker, New York; Mori, K., (1989) Tetrahedron, 45, p. 3233; Högberg, H.-E., (1992) Microbial Reagents in Organic Synthesis, pp. 399-410. , S. Servi, Ed., KlÌwer, Dordrecht; Högberg, H.-E., Berglund, P., Edlund, H., FÀhgerhag, J., Hedenström, E., Lundh, M., Nordin, O., Vörde, C., (1994) Catalysis Today, 22, p. 591; Berglund, P., Holmquist, M., Hedenström, E., Högberg, H.-E., Hult, K., (1993) Tetrahedron: Asymmetry, 4, p. 1869; Berglund, P., Vörde, C., Högberg, H.-E., (1994) Biocatalysis, 9, p. 123; Kodera, Y., Takahashi, K., Nishimura, H., Matsushima, A., Saito, Y., Inada, Y., (1986) Biotechnol. Lett., 8, p. 881; Engel, K.-H., (1991) Tetrahedron: Asymmetry, 2, p. 165; Sonnet, P.E., Baillargeon, M.W., (1991) Lipids, 26, p. 295; Holmberg, E., Holmquist, M., Hedenström, E., Berglund, P., Norin, T., Högberg, H.-E., Hult, K., (1991) Appl. Microbiol. Biotechnol., 35, p. 572; Högberg, H.-E., Edlund, H., Berglund, P., Hedenström, E., (1993) Tetrahedron: Asymmetry, 4, p. 2123; Chen, C.-S., Fujimoto, Y., Girdaukas, G., Sih, C.J., (1982) J. Am. Chem. Soc., 104, p. 7294; Wu, S.-H., Guo, Z.-W., Sih, C.J., (1990) J Am. Chem. Soc., 112, p. 1990; Tomizuka, N., Ota, Y., Yamada, K., (1966) Agric. Biol. Chem., 30, p. 576; Rúa, M.L., Díaz-Mauriño, T., Fernádez, V.M., Otero, C., Ballesteros, A., (1993) Biochim. Biophys. Acta, 1156, p. 181; Hernáiz, M.J., Sánchez-Montero, J.M., Sinisterra, J.V., (1994) Tetrahedron, 50, p. 10749; Colton, I.J., Ahmed, S.N., Kazlauskas, R.J., (1995) J. Org. Chem., 60, p. 212; Montero, S., Blanco, A., Virto, M.D., Landeta, L.C., Agud, I., Solozabal, R., Lascaray, J.M., Serra, J.L., (1993) Enzyme Microb. Technol., 15, p. 239; Wehtje, E., Adlercreutz, P., Mattiasson, B., (1992) Biocatalysis in Non-Conventional Media, pp. 377-382. , Tramper, J., Vermue, M. H., Beeftink, H. H. and von Stockar, U., Eds., Elsevier, Amsterdam; Berger, B., Faber, K.J., (1991) Chem. Soc., Chem Commun., p. 1198; Arroyo, M., Moreno, J.M., Sinisterra, J.V., (1993) J. Mol. Catal., 83, p. 261; St. Clair, N.L., Navia, M.A., (1992) J. Am. Chem. Soc., 114, p. 7314; ChiroCLEC-CR is the trade name for cross-linked C. rugosa lipase, marketed by Altus Biologics Inc. Cambridge, Ma, USALalonde, J.J., Govardhan, C., Khalaf, N., Martinez, A.G., Visuri, K., Margolin, A.L., (1995) J. Am. Chem. Soc., 117, p. 6845; Guo, Z.-W., Sih, C.J., (1989) J Am. Chem. Soc., 111, p. 6836; Rakels, J.L.L., Caillat, P., Straathof, A.J.J., Heijnen, J.J., (1994) Biotechnol. Prog., 10, p. 403; Berglund, P., Holmquist, M., Huit, K., Högberg, H.-E., (1995) Biotechnol. Lett., 17, p. 55; Kuhl, P., Halling, P.J., (1991) Biochim. Biophys. Acta, 1078, p. 326; Halling, P.J., (1992) Biotechnol. Techniques, 6, p. 271; Kvittingen, L., Sjursnes, B., Anthonsen, T., Halling, P., (1992) Tetrahedron, 48, p. 2793; Bergström, G., Wassgren, A.-B., Anderbrant, O., FÀgerhag, J., Edlund, H., Hedenström, E., Högberg, H.-E., Löfqvist, J., (1995) Experientia, 51, p. 370; Bovara, R., Carrea, G., Ottolina, G., Riva, S., (1993) Biotechnol. Lett., 15, p. 169 NR 20140805Available from: 2012-02-03 Created: 2012-02-03 Last updated: 2012-02-03Bibliographically approved

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