Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation

作者：Vismara Elena^*; Coletti Alessia; Valerio Antonio; Naggi AnnaMaria; Urso Elena; Torri Giangiacomo

来源：Molecules, 2012, 17(8): 9912-9930.

DOI：10.3390/molecules17089912

• sulfated C/O maltotriosyl dimers
• heparin
• kink motif
• NMR
• metastasis

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 alpha,alpha, alpha,beta and beta,beta 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 corresponding SMTCs. SMTCs were huge characterised by NMR spectroscopy which provided the sulfation degree, too alpha,alpha and alpha,beta were found quite homogeneous samples with a high degree of sulfation (85-95%). beta,beta appeared a non-homogeneous sample whose average sulfation degree was evaluated at around 78%. Mass spectroscopy experiments confirmed the sulfation degree range. Some considerations were proposed about SMTCs structure-biological properties.

• 出版日期2012-8