A chemoenzymic synthesis of 1,5-dideoxy-1,5-imino- l-mannitol and l-rhamnitol and investigation of their effects on glycosidases

• Published in: Carbohydrate research Vol. 239; pp. 155 - 166
• Main Authors: Zhou, Pengzu, Salleh, Hamzah Mohd, Chan, Phil C.M., Lajoie, Gilles, Honek, John F., Nambiar, P.T.Chandra, Ward, Owen P.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.02.1993; Elsevier Science
• Subjects: Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Exact sciences and technology; Organic chemistry; Preparations and properties; Enzyme; Nitrogen heterocycle; Ketose; Escherichia coli; Enzyme inhibitor; Competitive inhibition; Phosphorus Organic compounds; Biological activity; Aminoglycoside; Six membered ring; Glycosidase; Bacteria; Aldolase; Enterobacteriaceae; Enzymatic reaction
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/0008-6215(93)84211-N

1,5-Dideoxy-1,5-imino- l-rhamnitol ( 3) and 1,5-dideoxy-1,5-imino- l-mannitol ( 2), designed as inhibitors of α- l-rhamnosidase, have been synthesised from dihydroxyacetone phosphate and 3-azido-2-hydroxypropanal with the acid of partially purified E. coli l-rhamnulose 1-phosphate aldolase free of d-fructose 1,6-bisphosphate aldolase activity. Inhibitory effects of compounds 2, 3, 1,5-dideoxy-1,5-imino- d-mannitol, and 1,5-dideoxy-1,5-imino- d-glucitol ( 12) were tested on selected glycosidases. It has been found that compound 3 is a good inhibitor of α- l-rhamnosidase as well as α- l-fucosidases from bovine kidney and epididymis, 2 is a potent inhibitor of α-galactosidase and a moderate inhibitor of α- l-rhamnosidase, and 12 is a good inhibitor of α-galactosidase and α- l-rhamnosidase.