Drug Discoveries & Therapeutics
Online ISSN : 1881-784X
Print ISSN : 1881-7831
ISSN-L : 1881-7831
Original Articles
Galactosylation of caffeic acid by an engineered β-galactosidase
Lili LuYuchuan GuoLijuan XuTingting QiLan JinLi XuMin Xiao
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Supplementary material

2015 Volume 9 Issue 2 Pages 123-128

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Abstract

Glycosylation is useful for improving the chemical properties and physiological functions of biologically and pharmacologically important compounds. The glycosylation of phenolic compounds can increase their solubility and stability in water. The addition of galactose residue has special meaning as it facilitates targeted delivery of drugs to the liver cancer cells with abundant galactose acceptors on the cell surface. In this work, the engineered β-galactosidase W980F from Lactobacillus bulgaricus L3 was utilized for the glycosylation of caffeic acid, a well-known phenolic phytochemical with broad bioactivities. The reaction was performed by incubation of the enzyme with 200 mM of lactose and 100 mM of caffeic acid at 45°C for 1 h. The product was purified and analyzed by MS and NMR spectra. The MS revealed a signal of [M-H] at m/z 341.09, suggesting monogalactosylated products of caffeic acid (Mr 342). The NMR spectra further identified the products to be caffeic acid 3'-O-β- galactopyranoside and caffeic acid 4'-O-β-galactopyranoside in a ratio of 1:3. This was the first discovery that caffeic acid could be galactosylated by the engineered glycosidase.

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© 2015 International Research and Cooperation Association for Bio & Socio-Sciences Advancement
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