Publication: Lipase-catalyzed synthesis of hydrophobically modified dextrans: Activity and regioselectivity of lipase from Candida rugosa
Issued Date
2011-08-01
Resource Type
ISSN
13474421
13891723
13891723
Other identifier(s)
2-s2.0-79960734652
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Bioscience and Bioengineering. Vol.112, No.2 (2011), 124-129
Suggested Citation
Kultida Kaewprapan, Jirarut Wongkongkatep, Watanalai Panbangred, Pranee Phinyocheep, Emmanuelle Marie, Alain Durand, Pranee Inprakhon Lipase-catalyzed synthesis of hydrophobically modified dextrans: Activity and regioselectivity of lipase from Candida rugosa. Journal of Bioscience and Bioengineering. Vol.112, No.2 (2011), 124-129. doi:10.1016/j.jbiosc.2011.04.004 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/11508
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Title
Lipase-catalyzed synthesis of hydrophobically modified dextrans: Activity and regioselectivity of lipase from Candida rugosa
Abstract
Vinyl decanoate-modified dextran macromolecules (DexT40-VD) were synthesized in dimethyl sulfoxide at 50°C using lipase AY from Candida rugosa for catalyzing transesterification between polysaccharide and vinyl fatty esters. The extent of dextran modification (quantified by the molar ratio of attached alkyl tails to sugar repeat units) with native-, pH-adjusted-, 18-crown-6 ether pretreated pH-adjusted-, and stepwise addition of pretreated lipase AY yielded < 3%, 49%, 64% and 96% modified dextran respectively. Lipase AY accelerated the transesterification of DexT40 from 2- to 63-fold higher than the non-catalyzed system. This procedure was extended to other acyl donors showing that modification pattern exhibited regioselectivity depending on acyl donor structure. Regioselectivity equaled between 2- and 3-OH with saturated fatty acyl donors. The 2-OH was favored for unsaturated fatty acyl donors, while sterically hindered acyl donors oriented modification toward 3-OH position. DexT40-VD at 96% modification was a water-insoluble polymer forming 150. nm diameter nanoparticles in water which can be used as drug carrier systems. © 2011 The Society for Biotechnology, Japan.