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 (3)JH1-H2 coupling constant and (13)C 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.
ERATO Glycotrilogy Project, Japan Science and Technology Agency (JST), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
Sophon
S
Kaeothip
Akihiro
A
Ishiwata
Tasuku
T
Ito
Shinya
S
Fushinobu
Kiyotaka
K
Fujita
Yukishige
Y
Ito
D001089:Arabinose / Q000031:analogs & derivatives*; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D006026:Glycoside Hydrolases / Q000737:chemistry / Q000378:metabolism*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013379:Substrate Specificity
D001089:Arabinose; D006026:Glycoside Hydrolases
Enzyme substrate; PNP glycoside; Stereoselective synthesis; β-l-Arabinofuranosidase; β-l-Arabinofuranoside