Preparation of p-nitrophenyl β-l-arabinofuranoside as a substrate of β-l-arabinofuranosidase

• Synthesis of PNP β-l-Araf (1) as the substrate for novel β-l-Arafases has been achieved.
• NAP ether-mediated IAD afforded the desired PNP β-l-Araf (1) stereospecifically.
• PNP β-l-Araf (1) has been revealed to be an efficient substrate for HypBA1.

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.

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