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|
|Data di pubblicazione:||1998|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/S0144-8617(98)00074-5|
|Appare nelle tipologie:||01 - Articolo su rivista|