title: Highly efficient and enzymatic regioselective undecylenoylation of gastrodin in 2-methyltetrahydrofuran-containing systems.
abstract: Highly efficient and regioselective acylation of pharmacologically interesting gastrodin with vinyl undecylenic acid has been firstly performed through an enzymatic approach. The highest catalytic activity and regioselectivity towards the acylation of 7'-hydroxyl of gastrodin was obtained with Pseudomonas cepacia lipase. In addition, it was observed the lipase displayed higher activity in the eco-friendly solvent 2-methyltetrahydrofuran-containing systems than in other organic solvents. In the co-solvent mixture of tetrahydrofuran and 2-methyltetrahydrofuran (3/1, v/v), the reaction rate was 60.6 mM/h, substrate conversion exceeded 99%, and 7'-regioselectivity was 93%. It was also interesting that the lipase-catalyzed acylation couldn't be influenced by the benzylic alcohol in gastrodin. However, pseudomonas cepacia lipase displayed different regioselectivity towards gastrodin and arbutin.
authors.affiliation: Sericulture and Agri-Food Research Institute, Guangdong Academy of Agricultural Sciences, Guangzhou, China.
authors.forename: Rongling
authors.initials: R
authors.lastname: Yang
authors.affiliation: Sericulture and Agri-Food Research Institute, Guangdong Academy of Agricultural Sciences, Guangzhou, China.
authors.forename: Xueming
authors.initials: X
authors.lastname: Liu
authors.affiliation: Sericulture and Agri-Food Research Institute, Guangdong Academy of Agricultural Sciences, Guangzhou, China.
authors.forename: Zhiyi
authors.initials: Z
authors.lastname: Chen
authors.affiliation: Sericulture and Agri-Food Research Institute, Guangdong Academy of Agricultural Sciences, Guangzhou, China.
authors.forename: Chunying
authors.initials: C
authors.lastname: Yang
authors.affiliation: Sericulture and Agri-Food Research Institute, Guangdong Academy of Agricultural Sciences, Guangzhou, China.
authors.forename: Yaosheng
authors.initials: Y
authors.lastname: Lin
authors.affiliation: Sericulture and Agri-Food Research Institute, Guangdong Academy of Agricultural Sciences, Guangzhou, China.
authors.forename: Siyuan
authors.initials: S
authors.lastname: Wang
mesh_terms: D000215:Acylation; D001592:Benzyl Alcohols / Q000737:chemistry*; D016956:Burkholderia cepacia / Q000201:enzymology; D004795:Enzyme Stability; D005663:Furans / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry*; D007700:Kinetics; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D014476:Undecylenic Acids / Q000737:chemistry
chemical_list: D001592:Benzyl Alcohols; D005663:Furans; D005960:Glucosides; D012997:Solvents; D014476:Undecylenic Acids; C045345:gastrodin; D008049:Lipase; C550584:2-methyltetrahydrofuran; C538763:undecylenic acid