Molecules 2012, 17(8), 9912-9930; doi:10.3390/molecules17089912
Article

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

1,* email, 1email, 1email, 2email, 2email and 2email
Received: 4 July 2012; in revised form: 8 August 2012 / Accepted: 9 August 2012 / Published: 17 August 2012
(This article belongs to the Special Issue Advances in Carbohydrate Chemistry)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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 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.
Keywords: sulfated C/O maltotriosyl dimers; heparin; kink motif; NMR; metastasis
PDF Full-text Download PDF Full-Text [416 KB, Updated Version, uploaded 18 June 2014 19:53 CEST]
The original version is still available [421 KB, uploaded 18 June 2014 19:53 CEST]

Export to BibTeX |
EndNote


MDPI and ACS Style

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.

AMA Style

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.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert