Increasing the catalytic efficiency of Candida rugosa lipase for the synthesis of tert-alkyl butyrates in low-water media

References

• Bezbradica D, Mijin D, Siler-Marinkovic S, Knezevic Z. 2006. The Candida rugosa lipase catalyzed synthesis of amyl isobutyrate in organic solvent and solvent-free system: A kinetic study. J Mol Catal B: Enz 38:38–11.
   Google Scholar
• Bloomer S, Adlercreutz P, Mattiasson B. 1991. Triglyceride interesterification by lipases. Reaction parameters for the reduction of trisaturated impurities and diglycerides in batch reactions. Biocatal Biotransform 5:145–162.
   Google Scholar
• Bosley JA, Casey J, Macrae AR, MyCock G. 1997. Process for the esterification of carboxylic acids with tertiary alchols using a lipase from Candida antarctica. US patent 5658769. 5: 658–769.
   Google Scholar
• Bradford MM. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248–254.
   PubMed Web of Science ®Google Scholar
• Carrea G, Riva S. 2000. Properties and synthetic applications of enzymes in organic solvents. Angew Chem Int Ed 39: 2226 2254.
   Google Scholar
• Chowdary GV, Prafulla SG. 2002. The influence of water activity on the lipase catalyzed synthesis of butyl butyrate by Transesterification. Process Biochemistry 38:393–397.
   Web of Science ®Google Scholar
• Colton IJ, Ahmed SN, Kazlauskas RJ. 1995. A 2-propanol treatment increases the enantioselectivity of Candida rugosa lipase toward esters of chiral carboxylic acids. J Org Chem 60:212–217.
   Web of Science ®Google Scholar
• Dandavate V, Madamwar D. 2007. Novel approach for the synthesis of ethyl isovalerate using surfactant coated Candida rugosa lipase immobilized in microemulsion based organogel. Enzyme Microb Technol 41:265–270.
   Web of Science ®Google Scholar
• Dave R, Madamwar D. 2008. Candida rugosa lipase immobilized in Triton-X100 microemulsion based organogels (MBGs) for ester synthesis. Process Biochem 43:70–75.
   Web of Science ®Google Scholar
• Dave R, Madamwar D. 2010. Preparations for the use of Candida rugosa lipase in non-conventional solvents. Biocatal Biotransform 28(3):157–166.
   Google Scholar
• Decker LA. 1977. Worthington enzyme manual: enzymes, enzyme reagents related biochemicals. Freehold, New Jersey, USA.
   Google Scholar
• Forrat VJ, Ramon DJ, Yus M. 2008. Towards the continuous-flow synthesis of chiral tertiary alcohols by enantioselective addition of organozinc reagents to ketones using nanosize isoborneol ligands. Tetrahedron: Asymm 19:19–537.
   Google Scholar
• Forrat VJ, Ramon DJ, Yus M. 2005. Chiral tertiary alcohols from a trans-1-arenesulfonyl-amino-2-isoborneolsulfonylaminocyclohexane-catalyzed addition of organozinc to ketones. Tetrahedron: Asymm 16:16–3341.
   Google Scholar
• Gupta MN. 1992. Enzymes function in organic solvents. Eur J Biochem 203:25–32.
   PubMedGoogle Scholar
• Henke E, Pleiss J, Bornscheuer UT. 2002. Activity of lipases and esterases towards tertiary alcohols: insights into structure function relationship. Angew Chem Int Ed. 41:3211–3213.
   PubMed Web of Science ®Google Scholar
• Hou CT. 2005. Handbook of Industrial Biocatalysis. Florida, CRC press. p 11–17.
   Google Scholar
• Hudson EP, Eppler RK, Clark DS. 2005. Biocatalysis in semi-aqueous and nearly anhydrous conditions. Curr Opin Biotechnol 16:637–643.
   PubMed Web of Science ®Google Scholar
• Itoh T, Ohara H, Takagi Y, Kanda N, Uneyama K. 1993. Preparation of a new chiral building block for synthesizing broadly varied types of tertiary alcohols. Tetrahedron Lett 34:4215–4218.
   Google Scholar
• Kreiner M, Moore BD, Parker MC. 2001. Enzyme coated microcrystals: a one step method for high activity biocatalyst preparation. Chem Commun 1096–1097.
   Google Scholar
• Krishna SH, Persson M, Bornscheuer UT. 2002. Enantioselective transesterification of a tertiary alcohol by lipase A from Candida antarctica. Tetrahedron: Asymm 13:13–2693.
   Google Scholar
• Lee M-Y, Dordick JS. 2002. Enzyme activation for nonaqueous media. Curr Opin Biotechnol 13:376–384.
   PubMed Web of Science ®Google Scholar
• Lopez-Serrano P, Cao L, van Rantwijk F, Sheldon RA. 2002. Cross-linked enzyme aggregates with enhanced activity: application to lipases. Biotechnol Lett 24:1379–1383.
   Web of Science ®Google Scholar
• Majumder AB, Mondal K, Singh TP, Gupta MN. 2008. Designing cross-linked lipase aggregates for optimum performance as biocatalysts. Biocatal Biotransform 26:235–242.
   Web of Science ®Google Scholar
• Niederauer MQ, Glatz CF. 1992. Advances in biochemical engineering/ biotechnology. In: Niederauer MQ. Springer-Berlin/ Heidelberg, 47:159– 188.
   Google Scholar
• Nordblad M, Adlercreutz P. 2008. Effects of acid concentration and solvent choice on enzymatic acrylation by Candida antarctica lipase B. J Biotechnol 133:127–133.
   PubMed Web of Science ®Google Scholar
• O’Hagan D, Zaidi NA. 1994. The resolution of tertiary α-acetylene- acetate esters by the lipase from Candida cylindracea. Tetrahedron: Asymm 5:111–1118.
   Google Scholar
• Raghavan S, Sreekanth T. 2008. Stereoselective synthesis of chiral tertiary alcohol building blocks via neighbouring group participation from tri-substituted olefins. Tetrahedron Lett 49:1169–1174.
   Google Scholar
• Reslow M, Adlercreutz P, Mattiasson B. 1987. Organic solvents for bioorganic synthesis. Optimization of parameters for a chymotrypsin catalyzed process. Appl Microbiol Biotechnol 26:1 8.
   Google Scholar
• Roy I, Gupta MN. 2004a. Freeze drying of proteins: some emerging concerns. Biotechnol Appl Biochem 39:165–177.
   PubMed Web of Science ®Google Scholar
• Roy I, Gupta MN. 2004b. Preparation of highly active α-chymotrypsin for catalysis in organic media. Bioorg Med Chem Lett 14:2191–2193.
   PubMedGoogle Scholar
• Shah S, Gupta MN. 2007. Kinetic resolution of (±)-1-pheny lethanol in [Bmim][PF6] using high activity preparations of lipases. Bioorg Med Chem Lett 17:921–924.
   PubMed Web of Science ®Google Scholar
• Shah S, Sharma A, Gupta MN. 2008. Cross-linked protein-coated microcrystals ass biocatalysts in non-aqueous media. Biocatal Biotransform 26:266–271.
   Web of Science ®Google Scholar
• Sjursnes BJ, Anthonsen T. 1994. Acyl migration in 1, 2-Dibutyrin dependence on solvent and water activity. Biocatal Biotransform 9:285–297.
   Web of Science ®Google Scholar
• Sjursnes BJ, Kvittingen L, Anthonsen T. 1995. Regioselective lipase-catalyzed transesterification of tributyrin, influence of salt hydrates on acyl migration. J Am Oil Chem Soc 72:533–537.
   Google Scholar
• Stähl M, Mänsson M-O, Mosbach K. 1990. The synthesis of a D-amino acid ester in an organic media with α-chymotrypsin modified by a bio-imprinting procedure. Biotechnol Lett 13: 161–166.
   Google Scholar
• Zaks A, Klibanov AM. 1988. Effect of water on enzyme action in organic media. J Biol Chem 263:8017–8021.
   Google Scholar
• Zaks A, Klibanov AM. 1994. Enzyme catalysis in organic media at 100°C. Science 224:1249–1251.
   Google Scholar