Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation
AbstractThis 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 a,a, a,b and b,b 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. a,a and a,b were found quite homogeneous samples with a high degree of sulfation (85–95%). b,b 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. View Full-Text
- Supplementary File 1:
PDF-Document (PDF, 3283 KB)
Scifeed alert for new publicationsNever miss any articles matching your research from any publisher
- Get alerts for new papers matching your research
- Find out the new papers from selected authors
- Updated daily for 49'000+ journals and 6000+ publishers
- Define your Scifeed now
Vismara, E.; Coletti, A.; Valerio, A.; Naggi, A.; Urso, E.; Torri, G. Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation. Molecules 2012, 17, 9912-9930.
Vismara E, Coletti A, Valerio A, Naggi A, Urso E, Torri G. Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation. Molecules. 2012; 17(8):9912-9930.Chicago/Turabian Style
Vismara, Elena; Coletti, Alessia; Valerio, Antonio; Naggi, Annamaria; Urso, Elena; Torri, Giangiacomo. 2012. "Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation." Molecules 17, no. 8: 9912-9930.