Abstract
In the present study, Candida antarctica lipase B (CALB) was conjugated with Pluronic polymers, a family of amphiphilic triblock copolymers made of a central hydrophobic polypropylene oxide block connected to two hydrophilic poly(ethylene oxide) side blocks, and tested for the chemo-enzymatic epoxidation of fatty acids conducted in organic media. The effects of operation parameters including the type of Pluronic polymers and solvents on the epoxidation of different plant oil substrates were examined, in which Pluronic F127 and toluene appeared the best polymer and solvent, respectively. At optimized conditions, an yield of 97, 75, 67 % for epoxidized oleic acid, linoleic acid, linolenic acid, respectively, was obtained using Pluronic F127 conjugated CALB. This study suggested that CALB-Pluronic conjugate is an appealing enzyme catalyst for the epoxidation in organic media.
Graphical Abstract
An enzymatic approach to epoxidation of fatty acids was investigated using a lipase-Pluronic conjugate as the catalyst.
Similar content being viewed by others
References
Fitzpatrick PA, Klibanov AM (1991) J Am Chem Soc 113:3166–3171
Schmid RD, Verger R (1998) Angew Chem Int Ed 37:1608–1633
Dordick JS (2013) Biocatalysts for industry. Springer, New York
Zaks A, Klibanov AM (1984) Science 224:1249–1251
Okazaki S, Kamiya N, Abe K, Goto M, Nakashio F (1997) Biotechnol Bioeng 55:455–460
Abe K, Goto M, Nakashio F (1997) J Ferment Bbioeng 83:555–560
Zhang Z, Fukunaga K, Sugimura Y, Nakao K, Shimizu T (1996) Carbohydr Res 290:225–232
Wang YF, Lalonde JJ, Momongan M, Bergbreiter DE, Wong CH (1988) J Am Chem Soc 10:7200–7205
Laane C, Boeren S, Vos K, Veeger C (1987) Biotechnol Bioeng 30:81–87
Shield JW, Ferguson HD, Bommarius AS, Hatton TA (1986) Ind Eng Chem Fundam 25:603–612
Kim J, Grate JW, Wang P (2008) Trends Biotechnol 26:639–646
Ge J, Yang C, Zhu J, Lu D, Liu Z (2012) Top Catal 55:1070–1080
Zhu J, Zhang Y, Lu D, Zare RN, Ge J, Liu Z (2013) Chem Commun 49:6090–6092
Zhang Y, Dai Y, Hou M, Li T, Ge J, Liu Z (2013) RSC Adv 3:22963–22966
Joseph R, Madhusoodhanan KN, Alex R, Varghese S, George KE, Kuriakose B (2004) Plast Rubber Compos 33:217–222
Benaniba MT, Belhaneche-Bensemra N, Gelbard G (2003) Polym Degrad Stab 82:245–249
John J, Bhattacharya M, Turner RB (2002) J Appl Polym Sci 86:3097–3107
Ahmad S, Ashraf SM, Hasnat A (2002) Paintindia 52:47–52
Adhvaryu A, Erhan SZ (2002) Ind Crop Prod 15:247–254
Hong CK, Wool RP (2005) J Appl Polym Sci 95:1524–1538
Khot SN, Lascala JJ, Can E, Morye SS, Williams GI, Palmese GR, Kusefoglu SH, Wool RP (2001) J Appl Polym Sci 82:703–723
Klaas MR, Warwel S (1999) Ind Crop Prod 9:125–132
Klaas MR, Warwel S (1996) J Am Oil Chem Soc 73:1453–1457
Ding Z, Chen G, Hoffman AS (1996) Bioconjug Chem 7:121–125
Klibanov AM (1997) J Biotechnol 15:97–101
Yong Y, Zhu J, Lu D, Ge J, Liu Z (2015) CIESC J 66:2534–2539
Acknowledgments
This work was supported by Tsinghua University Foundation 20141081143.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yuki, O., Zhang, Y., Ge, J. et al. Epoxidation of Fatty Acids by Pluronic-Conjugated Lipase in Organic Media. Catal Lett 146, 1073–1078 (2016). https://doi.org/10.1007/s10562-016-1726-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-016-1726-5