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

Autor:	Yifei Zhang, Zhixian Li, Jun Ge, Pingkai Ouyang, Meng Meng Lin, Zheng Liu
Rok vydání:	2013
Předmět:	biology Chemistry Organic Chemistry Clindamycin Regioselectivity Prodrug biology.organism_classification Combinatorial chemistry Chemical synthesis Catalysis Acylation medicine biology.protein Candida antarctica Physical and Theoretical Chemistry Lipase medicine.drug
Zdroj:	Organic Process Research & Development. 17:1179-1182
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op400135y
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0d37d3b9808e339153cf1ecd36f679e1 https://doi.org/10.1021/op400135y Zobrazit plný text záznamu