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

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

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

Content Provider	MDPI
Author	Vismara, Elena Coletti, Alessia Valerio, Antonio Naggi, Annamaria Urso, Elena Torri, Giangiacomo
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.
File Size	425984
Ending Page	9930
Page Count	19
Starting Page	9912
File Format	PDF
e-ISSN	14203049
DOI	10.3390/molecules17089912
Journal	Molecules
Issue Number	8
Volume Number	17
Language	English
Publisher Date	2012-08-17
Access Restriction	Open
Subject Keyword	sulfated C/O maltotriosyl dimers heparin kink motif NMR metastasis
Content Type	Text
Resource Type	Article

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