title: Novel and highly efficient regioselective route to helicid esters by lipozyme TLL.
abstract: Highly regioselective acylation of helicid with fatty acid vinyl esters catalyzed by the lipase from Thermomyces lanuginosus has been successfully performed for the first time. For the enzymatic caproylation of helicid, under the optimal conditions, initial reaction rate was 33.2 mM/h, and substrate conversion and regioselectivity were greater than 99%. In addition, the acyl recognition of the enzyme in the regioselective acylation of helicid was investigated. The results showed that although 6'-O-acyl derivatives of helicid were exclusively obtained with all the tested acyl donors, the enzymatic reaction rate varied widely with different acyl donors, presumably owing to their different interactions with the active site of the lipase. It is also interesting that the different configuration of only one hydroxyl group at C-3 in helicid couldn't affect the lipase-catalyzed esterification and helicid has the same regioselectivity as that of D-glucose 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.forename: Xiangjie
authors.initials: X
authors.lastname: Zhao
authors.forename: Xueming
authors.initials: X
authors.lastname: Liu
mesh_terms: D000215:Acylation; D001203:Ascomycota / Q000201:enzymology*; D055162:Biocatalysis; D004795:Enzyme Stability; D004952:Esters / Q000737:chemistry* / Q000378:metabolism*; D008049:Lipase / Q000378:metabolism*; D009005:Monosaccharides / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism; D013997:Time Factors
chemical_list: D004952:Esters; D009005:Monosaccharides; C512250:formylphenyl-O-beta-D-pyranosyl alloside; C093666:Lipozyme; D008049:Lipase