Synthesis of L-fucopyranosyl-4-thiodisaccharides from levoglucosenone and their inhibitory activity on α-L-fucosidase

Bioorganic & Medicinal Chemistry Letters
1995.0

Abstract

A new method of stereos, elective synthesis of 0c-(1-4) linked thiodisaccharides: 4-S-(o~-L-fucopyranosyl)-4-thio-3-deoxy-ot-D-glucopyranose 6 and 2-acetamido-2,3 dideoxy-4-tbio-(et-L-fucopyranosyl)-4-thio-0c-D-glucopyranose 7, by Michael addition of 1-thio-~-L-fucopyranoside to levoglucosenone is described. The inhibition study of 6 and 7, against ot-L-fucosidase (from bovine kidney) indicates the importance of 3-deoxy position of glucosamine moiety for total inhibitory effect Ki=4.0mM and K~=2.4mM respectivelly.

Knowledge Graph

Similar Paper

Synthesis of L-fucopyranosyl-4-thiodisaccharides from levoglucosenone and their inhibitory activity on α-L-fucosidase
Bioorganic & Medicinal Chemistry Letters 1995.0
Thio-sugars IV: Design and synthesis of S-linked fucoside analogs as a new class of α-L-fucosidase inhibitors
Bioorganic & Medicinal Chemistry Letters 1998.0
Synthesis of all-cis 2,5-imino-2,5-dideoxy-fucitol and its evaluation as a potent fucosidase and galactosidase inhibitor
Bioorganic & Medicinal Chemistry Letters 2010.0
Synthesis and evaluation of amino-threoses in d- and l-series: Are five membered ring amino-sugars more potent glycosidase inhibitors than the six membered ones?
Bioorganic & Medicinal Chemistry 2007.0
Convenient synthesis and evaluation of enzyme inhibitory activity of several N-Alkyl-, N-Phenylalkyl, and cyclic isourea derivatives of 5a-Carba-α-dl-fucopyranosylamine
Bioorganic & Medicinal Chemistry Letters 2002.0
Synthesis of inhibitors of α-1,3-fucosyltransferase
Bioorganic & Medicinal Chemistry Letters 1997.0
Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases
Bioorganic & Medicinal Chemistry 2013.0
Synthesis of Sulfur-Containing Analogues of Hedychenone, a Labdane Diterpenoid from Hedychium spicatum
Journal of Natural Products 2022.0
Synthesis of and glycosidase inhibition by α-l-homofuconojirimycin
Bioorganic & Medicinal Chemistry Letters 1993.0
Asymmetric synthesis of the l-fuco-nojirimycin, a nanomolar α-l-fucosidase inhibitor
Bioorganic & Medicinal Chemistry Letters 2006.0