The review article describes the synthesis of different C-glycoside mimetics of glycosylphosphates, glycolipids, glycosyl amino acids and oligosaccharides. In particular, the phosphono analogues of α-L-rhamnose 1-phosphate, N-acetyl-α-D-glucosamine and N-acetyl-α-D-mannosamine-1-phosphate were synthesised; the last two from a C-2-deprotected α-C-glucopyranoside, the free hydroxyl group of which was finally converted into an amino group. In this context a method for the deprotection of allyl C-glycosides at C-2 is also reported. Analogues of glycosyl glycerols were obtained by reaction of a malonyl radical with glycoexoenitols and reduction of the obtained β-C-glycosyl malonate. Acylation gave the analogues of glyceroglycolipids. A C-glucosyl amino acid was obtained exploiting a Wittig rearrangement of compound 38. Naphthoquinone was attached, through C-C bonds, to the anomeric centre of a sugar and the non-reducing end of a different sugar, so affording a mimic of a trisaccharide. © 1998 Elsevier Science Ltd. All rights reserved.

Cipolla, L., LA FERLA, B., & Nicotra, F. (1998). Synthesis of potential inhibitors of carbohydrate processing enzymes. CARBOHYDRATE POLYMERS, 37(3), 291-298 [10.1016/S0144-8617(98)00074-5].

Synthesis of potential inhibitors of carbohydrate processing enzymes

CIPOLLA, LAURA FRANCESCA;LA FERLA, BARBARA;NICOTRA, FRANCESCO
1998

Abstract

The review article describes the synthesis of different C-glycoside mimetics of glycosylphosphates, glycolipids, glycosyl amino acids and oligosaccharides. In particular, the phosphono analogues of α-L-rhamnose 1-phosphate, N-acetyl-α-D-glucosamine and N-acetyl-α-D-mannosamine-1-phosphate were synthesised; the last two from a C-2-deprotected α-C-glucopyranoside, the free hydroxyl group of which was finally converted into an amino group. In this context a method for the deprotection of allyl C-glycosides at C-2 is also reported. Analogues of glycosyl glycerols were obtained by reaction of a malonyl radical with glycoexoenitols and reduction of the obtained β-C-glycosyl malonate. Acylation gave the analogues of glyceroglycolipids. A C-glucosyl amino acid was obtained exploiting a Wittig rearrangement of compound 38. Naphthoquinone was attached, through C-C bonds, to the anomeric centre of a sugar and the non-reducing end of a different sugar, so affording a mimic of a trisaccharide. © 1998 Elsevier Science Ltd. All rights reserved.
Articolo in rivista - Articolo scientifico
carbohydrates, glycomimetics, enzyme inhibitors
English
291
298
8
Cipolla, L., LA FERLA, B., & Nicotra, F. (1998). Synthesis of potential inhibitors of carbohydrate processing enzymes. CARBOHYDRATE POLYMERS, 37(3), 291-298 [10.1016/S0144-8617(98)00074-5].
Cipolla, L; LA FERLA, B; Nicotra, F
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/16667
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