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Lipase-catalyzed synthesis of L-phenylalanyl-D-glucose.

Lohith, K. and Divakar, S. (2005) Lipase-catalyzed synthesis of L-phenylalanyl-D-glucose. Journal of biotechnology, 117 (1). pp. 49-56. ISSN 0168-1656

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Abstract

Regioselective synthesis of L-phenylalanyl ester of D-glucose with unprotected L-phenylalanine and D-glucose was carried out in organic solvents using lipases from Rhizomucor miehei (RML) and porcine pancreas (PPL). The reaction was investigated in terms of free unprotected L-phenylalanine, D-glucose, RML and PPL concentrations, buffer salts (pH and concentration), enzyme reusability and incubation period. Under the experimental conditions employed, both the enzymes exhibited good esterification potentialities, with RML exhibiting better conversions (maximum yield, 98%) than PPL (maximum yield, 75.6%). Reactions in the presence of buffer salts gave about 10% higher yields than those in their absence. Two-dimensional heteronuclear single quantum coherence transfer (HSQCT) NMR spectral analysis confirmed the formation of five diastereomeric esters: three different L-phenylalanyl-D-glucose monoesters (6-O: 24.1%, 3-O: 23.3% and 2-O: 19.2%) and two different diesters (2,6-di-O: 16.6% and 3,6-di-O: 16.8%) in an esterification yield of 92.4%.

Item Type: Article
Uncontrolled Keywords: Diastereomeric diesters; Esterification; Diastereomeric monoesters; l-Phenylalanyl-d-glucose; Porcine pancreas lipase; Rhizomucor miehei lipase; Unprotected amino acids
Subjects: 600 Technology > 08 Food technology > 16 Nutritive value > 05 Enzymes
Divisions: Fermentation Technology and Bioengineering
Depositing User: Food Sci. & Technol. Information Services
Date Deposited: 04 Aug 2008 09:31
Last Modified: 03 Oct 2018 05:54
URI: http://ir.cftri.com/id/eprint/1992

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