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.
Citazione: | Cipolla, L., La Ferla, B., & Nicotra, F. (1998). Synthesis of potential inhibitors of carbohydrate processing enzymes. CARBOHYDRATE POLYMERS, 37(3), 291-298. |
Tipo: | Articolo in rivista - Articolo scientifico |
Carattere della pubblicazione: | Scientifica |
Titolo: | Synthesis of potential inhibitors of carbohydrate processing enzymes |
Autori: | Cipolla, L; La Ferla, B; Nicotra, F |
Autori: | |
Data di pubblicazione: | 1998 |
Lingua: | English |
Rivista: | CARBOHYDRATE POLYMERS |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/S0144-8617(98)00074-5 |
Appare nelle tipologie: | 01 - Articolo su rivista |