Zhixiang Li, Yifei Zhang, Mengmeng Lin
Aug 23, 2013
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Influential Citations
20
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Journal
Organic Process Research & Development
Abstract
Chemical synthesis of clindamycin palmitate, a prodrug with taste greatly improved more than that of clindamycin, involves laborious steps of protection and deprotection to achieve the monoacylation only at 2-hydroxyl group of clindamycin and gives an overall yield below 50%. Here we report the first example of one-step synthesis of clindamycin palmitate with high regioselectivity using immobilized Candida antarctica lipase B (Novozym 435) as the catalyst. The lipase-catalyzed synthesis reached a conversion above 90% in 12 h using toluene as solvent and, moreover, a highly regioselective acylation at the 2-hydroxyl of clindamycin. The significantly improved conversion achieved at an excellent regioselectivity makes this enzymatic process attractive for the synthesis of clindamycin ester derivatives.