title: Highly regioselective synthesis of undecylenic acid esters of purine nucleosides catalyzed by Candida antarctica lipase B.
abstract: Regioselective undecylenoylation of purine nucleosides as potential dual prodrugs was achieved by Candida antarctica lipase B using adenosine as a model reactant. The optimum organic solvent, molar ratio of vinyl ester to nucleoside, enzyme dosage, reaction temperature and molecular sieve amount were anhydrous THF, 5:1, 20 U/ml, 45°C and 75 mg/ml, respectively. Under the optimum conditions, the initial reaction rate, yield and 5'-regioselectivity were 1.1 mM/h, 90% and >99%, respectively. The enzymatic acylation of various nucleosides furnished the desired 5'-ester derivatives with the yields of 60-95% and 5'-regioselectivities of >99%. In addition, the lipase displayed excellent operational stability in THF, and retained 96% of its initial activity after reused for five batches.
authors: State Key Laboratory of Pulp and Paper Engineering, College of Light Industry and Food Sciences, South China University of Technology, Guangzhou, China.
authors: Wen-Li
authors: WL
authors: Gao
authors: Ning
authors: N
authors: Li
authors: Min-Hua
authors: MH
authors: Zong
mesh_terms: D002175:Candida / Q000201:enzymology* / Q000378:metabolism*; D004795:Enzyme Stability; D004952:Esters / Q000737:chemistry / Q000378:metabolism*; D005656:Fungal Proteins; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D011684:Purine Nucleosides / Q000737:chemistry / Q000378:metabolism*; D012997:Solvents; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature; D014476:Undecylenic Acids / Q000737:chemistry / Q000378:metabolism*
chemical_list: D004952:Esters; D005656:Fungal Proteins; D011684:Purine Nucleosides; D012997:Solvents; D014476:Undecylenic Acids; D008049:Lipase; C431349:lipase B, Candida antarctica