A Facile Synthesis of 4-Methylumbelliferyl (1-->3)-β-D-Pentaglucoside

Title: A Facile Synthesis of 4-Methylumbelliferyl (1-->3)-β-D-Pentaglucoside

Volume: 5 Issue: 6

Author(s): G. L. Huang

Affiliation:

Keywords: Yeast glucan, 4-Methylumbelliferyl (1→3)-β-D-pentaglucoside, Synthesis, Fungal enzymatic activity

Abstract: The synthesis and stability assay of 4-methylumbelliferyl (1→3)-β-D-pentaglucoside 3 are described. The acid-solubilized (1→3)-β-D-oligoglucosides were prepared by partial acid hydrolysis of glucan. The peracetylated (1→3)-β-D-pentaglucoside 1 was obtained by isolation of peracetylated (1→3)-β-D-oligoglucoside mixture. The peracetylated 4-methylumbelliferyl (1→3)-β-D-pentaglucoside 2 was synthesized by treating compound 1 with the 4-methylumbelliferone and a Lewis acid (SnCl4) catalyst. NaOMe in dry methanol was used for the deacetylation of the blocked derivative, to give the target compound 3 in an overall yield of 35%. In the activity assays of fungal β-glucosidase, it indicates that compound 3 is much more stable than the corresponding pentasaccharide.

Cite this article as:

Huang L. G., A Facile Synthesis of 4-Methylumbelliferyl (1-->3)-β-D-Pentaglucoside, Letters in Drug Design & Discovery 2008; 5 (6) . https://dx.doi.org/10.2174/157018008785777298