Anti-metastatic semi-synthetic sulfated maltotriose C-C linked dimers. Synthesis and characterisation.

ABSTRACT: This manuscript describes the preparation and the spectroscopic characterisation of semi-synthetic sulfated maltotriose C-C linked dimers (SMTCs) where the natural C-O-C anomeric bond was substituted by one direct central C-C bond. This C-C bond induces conformation and flexibility changes with respect to the usual anomeric bond. SMTCs neutral precursors came from maltotriosyl bromide electroreduction through maltotriosyl radical intermediate dimerisation. The new C-C bond configuration, named for convenience α,α, α,β and β,β as the natural anomeric bond, dictated the statistic ratio formation of three diastereoisomers. They were separated by silica gel flash chromatography followed by semi preparative HPLC chromatography. Each diastereoisomer was exhaustively sulfated to afford the corres

SUBMITTER: Vismara E 

PROVIDER: S-EPMC3646267 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature