Lipase-Catalyzed One-Step and Regioselective Synthesis of Clindamycin Palmitate

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• 作者：Zhixian Li ; Yifei Zhang ; Mengmeng Lin ; Pingkai Ouyang ; Jun Ge ; Zheng Liu
• 刊名：Organic Process Research & Development
• 出版年：2013
• 出版时间：September 20, 2013
• 年：2013
• 卷：17
• 期：9
• 页码：1179-1182
• 全文大小：254K
• 年卷期：v.17,no.9(September 20, 2013)
• ISSN：1520-586X

文摘

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.