22796-65-2Relevant academic research and scientific papers
Preparation of p-nitrophenyl β-l-arabinofuranoside as a substrate of β-l-arabinofuranosidase
Kaeothip, Sophon,Ishiwata, Akihiro,Ito, Tasuku,Fushinobu, Shinya,Fujita, Kiyotaka,Ito, Yukishige
, p. 95 - 100 (2013/12/04)
Synthesis of p-nitrophenyl β-l-arabinofuranoside 1 as the substrate for novel β-l-arabinofuranosidase has been achieved by using both our inter- and intra-molecular glycosylation methodologies. Although the intermolecular glycosylation with l-Araf donors 3 and 4 resulted in a mixture of both α- and β-isomers, NAP ether-mediated IAD with 3 and 6 afforded the desired β-l-arabinofuranoside stereospecifically which was confirmed by NMR analysis on the 3JH1-H2 coupling constant and 13C chemical shift of C1. As expected, 1 has been revealed to be an efficient substrate in the biological study of a novel β- arabinofuranosidase such as HypBA1 with higher apparent affinity compared with other reported substrates.
Preparation of regioselectively feruloylated p-nitrophenyl α-l-arabinofuranosides and β-d-xylopyranosides-convenient substrates for study of feruloyl esterase specificity
Mastihubova, Maria,Biely, Peter
experimental part, p. 1094 - 1098 (2010/09/12)
p-Nitrophenyl α-l-arabinofuranoside and β-d-xylopyranoside mono-O-ferulates were prepared by 4-O-acetylferuloylation of corresponding enzymatically prepared di-O-acetates followed by deacetylation. An alternative mild acylation catalysed by zinc oxide was tested on xylopyranoside derivatives. The chemoselective methanolysis of the acetyl groups using neutral catalyst dibutyltin oxide at reflux was used as deacetylation method. Under these conditions a significant feruloyl migration was observed mainly on p-nitrophenyl 3-O-feruloyl-β-d-xylopyranoside resulting in low yields of the positional isomers. Investigation of substrate and positional specificity of different types of feruloyl esterases on the presented compounds in enzyme-coupled assays was reported previously.
The acetates of p-nitrophenyl α-L-arabinofuranoside - Regioselective preparation by action of lipases
Mastihubova, Maria,Szemesova, Jana,Biely, Peter
, p. 1805 - 1810 (2007/10/03)
All possible di-O-acetates and mono-O-acetates of p-nitrophenyl α-l-arabinofuranoside were prepared by chemoenzymatic way using lipases. The 2,3-di-O-acetate was obtained in 90% yield by deacetylation of the primary acetyl group of per-O-acetylated p-nitr
Enzymatic synthesis of alkyl arabinofuranosides using a thermostable α-L-arabinofuranosidase
Rémond, Caroline,Ferchichi, Mounir,Aubry, Nathalie,Plantier-Royon, Richard,Portella, Charles,O'Donohue, Michael J.
, p. 9653 - 9655 (2007/10/03)
A thermostable α-L-arabinofuranosidase was tested for its ability to perform transglycosylation with different alcohol acceptors. Reactions were characterized by high rates with optimal synthesis being obtained within 10 min. Both primary and secondary al
