Regio-selective acylation of biologically important iridoid glycosides by Candida antarctica lipase

• Published in: Journal of Molecular Catalysis B: Enzymatic
• Main Authors: Singh, Parvinder Pal, Qazi, Naveed Ahmed, Shafi, Syed, Reddy, D. Mahendhar, Banday, Abid H., Reddy, P. Bhaskar, Suri, K.A., Gupta, B.D., Satti, N.K., Wakhloo, Basant P., Kumar, H.M. Sampath, Qazi, G.N.
• Format: Article in Journal/Newspaper
• Language: unknown
• Published: 2009
• Subjects: Chemical Sciences; Antarc*; Antarctica
• Online Access: http://iiim.csircentral.net/331/; http://iiim.csircentral.net/331/1/10.1016j.molcatb.2008.04.005.pdf; https://doi.org/10.1016/j.molcatb.2008.04.005

Lipase catalyzed regio-selective acylation of five iridoid glycosides viz., picroside I&II, catalpol, agnuside and negundoside in the presence of various acyl donors such as vinyl acetate and p-nitrophenyl alkanoates was studied. The regio-selectivity of enzymatic acylation and yieldswere found to vary amongst different substrates. Monoacylated products were isolated with all the substrates under scrutiny indicating high regio-selective nature of such transformations. A series of acyl esters of picroside-I, picroside-II, catalpol, agnuside and negundoside have been synthesized by this enzymatic trans-esterification methodology.