cas 6892-58-6, 4-NITROPHENYL-ALPHA-L-ARABINOFURANOSIDE | Articles data ｜lookchem

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6892-58-6

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Preparation of p-nitrophenyl β-l-arabinofuranoside as a substrate of β-l-arabinofuranosidase
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.
Kaeothip, Sophon,Ishiwata, Akihiro,Ito, Tasuku,Fushinobu, Shinya,Fujita, Kiyotaka,Ito, Yukishige
p. 95 - 100
(2013/12/04)

Preparation of regioselectively feruloylated p-nitrophenyl α-l-arabinofuranosides and β-d-xylopyranosides-convenient substrates for study of feruloyl esterase specificity
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.
Mastihubova, Maria,Biely, Peter
experimental part
p. 1094 - 1098
(2010/09/12)

The acetates of p-nitrophenyl α-L-arabinofuranoside - Regioselective preparation by action of lipases
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
Mastihubova, Maria,Szemesova, Jana,Biely, Peter
p. 1805 - 1810
(2007/10/03)

Enzymatic synthesis of alkyl arabinofuranosides using a thermostable α-L-arabinofuranosidase
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
Rémond, Caroline,Ferchichi, Mounir,Aubry, Nathalie,Plantier-Royon, Richard,Portella, Charles,O'Donohue, Michael J.
p. 9653 - 9655
(2007/10/03)

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Chemical Properties

Appearance/Colour :white to slightly yellowish crystalline powder
Melting Point: 157-159℃
Boiling Point: 553.7oC at 760 mmHg
Flash Point:288.7oC
Density: 1.562g/cm3
Solubility:methanol: 50 mg/mL, clear, light yellow
Storage Temp.:−20°C
Vapor Pressure: 4.29E-13mmHg at 25°C
PKA: 12.77±0.70(Predicted)
BRN: 1688357
PSA: 124.97000
LogP: -0.06420

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