Concise synthesis of 4-methylumbelliferyl-penta-N-acetylchitopentaoside and its inhibition effect on chitinase.
The synthesis of 4-methylumbelliferyl (UMB)-penta-N-acetylchitopentaoside 4 and its inhibition effect on chitinase are described. The fluorophore-assisted carbohydrate electrophoresis (FACE) analysis showed that the partially N-acetylated chitooligosaccharide (COS) mixture mainly contained glucosamine (GlcN) and oligomers [(GlcN)n, n=2-7]. The peracetylated COSs [(GlcNAc)(n), n=1-7] were synthesized by treating the partially N-acetylated COS mixture with Ac2O-NaOAc. The peracetylated chitopentaoside 1 was obtained by isolation of peracetylated COS mixture. The peracetylated UMB chitopentaoside 3 was synthesized by treating compound 1 with 4-methylumbelliferone and a Lewis acid (SnCl4) catalyst. NaOMe in dry methanol was used for deacetylation of the blocked derivative, to give the target compound 4 in an overall yield of 32%. In binding chitinase assay, it indicates that compound 4 is much more stable than the corresponding penta-N-acetylchitopentaose 2.
Huang
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College of Chemistry, Chongqing Normal University, Chongqing 400047, China. huangdoctor226@163.com
D000107:Acetylation; D002688:Chitinases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D004586:Electrophoresis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D010084:Oxidation-Reduction; D014468:Umbelliferones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*
C546456:4-methylumbelliferyl-penta-N-acetylchitopentaoside; D004791:Enzyme Inhibitors; D009844:Oligosaccharides; D014468:Umbelliferones; D002688:Chitinases