Synthesis and stability assay of 4-methylumbelliferyl (1-->3)-beta-D-pentaglucoside.
The synthesis and stability of 4-methylumbelliferyl (1 --> 3)-beta-D-pentaglucoside 3 are described. The (1 --> 3)-beta-D-glucan isolated from the cell walls of Saccharomyces cerevisiae was recovered from the aqueous medium as water-insoluble particles by the spray drying (GS) method. The acid-solubilized (1 --> 3)-beta-D-oligoglucosides were prepared by partial acid hydrolysis of glucan. The peracetylated (1 --> 3)-beta-D-pentaglucoside 1 was obtained by isolation of peracetylated (1 --> 3)-beta-D-oligoglucoside mixture. The peracetylated 4-methylumbelliferyl (1 --> 3)-beta-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%. Activity assays with beta-glucosidase indicated that compound 3 was much more stable than the corresponding pentasaccharide.
Huang
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College of Chemistry, Chongqing Normal University, Chongqing, China. huangdoctor226@163.com
D000085:Acetates / Q000138:chemical synthesis; D005960:Glucosides / Q000138:chemical synthesis*; D006868:Hydrolysis; D006923:Hymecromone / Q000031:analogs & derivatives / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis*; D012441:Saccharomyces cerevisiae / Q000378:metabolism; D014468:Umbelliferones / Q000138:chemical synthesis*; D047071:beta-Glucans / Q000378:metabolism; D001617:beta-Glucosidase / Q000378:metabolism
C542483:4-methylumbelliferyl-1-3-pentaglucoside; D000085:Acetates; D005960:Glucosides; D009844:Oligosaccharides; D014468:Umbelliferones; D047071:beta-Glucans; C542484:peracetylated-1-3-pentaglucoside; C542485:peracetylated-4-methylumbelliferyl-1-3-pentaglucoside; D006923:Hymecromone; D001617:beta-Glucosidase