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

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 resp...

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Autores principales: Vismara, Elena, Coletti, Alessia, Valerio, Antonio, Naggi, AnnaMaria, Urso, Elena, Torri, Giangiacomo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3646267/
https://www.ncbi.nlm.nih.gov/pubmed/22902885
http://dx.doi.org/10.3390/molecules17089912
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author Vismara, Elena
Coletti, Alessia
Valerio, Antonio
Naggi, AnnaMaria
Urso, Elena
Torri, Giangiacomo
author_facet Vismara, Elena
Coletti, Alessia
Valerio, Antonio
Naggi, AnnaMaria
Urso, Elena
Torri, Giangiacomo
author_sort Vismara, Elena
collection PubMed
description 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 corresponding SMTCs. SMTCs were huge characterised by NMR spectroscopy which provided the sulfation degree, too. α,α and α,β were found quite homogeneous samples with a high degree of sulfation (85–95%). β,β 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.
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spelling pubmed-36462672013-05-07 Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation Vismara, Elena Coletti, Alessia Valerio, Antonio Naggi, AnnaMaria Urso, Elena Torri, Giangiacomo Molecules Article 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 corresponding SMTCs. SMTCs were huge characterised by NMR spectroscopy which provided the sulfation degree, too. α,α and α,β were found quite homogeneous samples with a high degree of sulfation (85–95%). β,β 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. MDPI 2012-08-17 /pmc/articles/PMC3646267/ /pubmed/22902885 http://dx.doi.org/10.3390/molecules17089912 Text en © 2012 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee MDPI, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Vismara, Elena
Coletti, Alessia
Valerio, Antonio
Naggi, AnnaMaria
Urso, Elena
Torri, Giangiacomo
Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation
title Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation
title_full Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation
title_fullStr Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation
title_full_unstemmed Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation
title_short Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation
title_sort anti-metastatic semi-synthetic sulfated maltotriose c-c linked dimers. synthesis and characterisation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3646267/
https://www.ncbi.nlm.nih.gov/pubmed/22902885
http://dx.doi.org/10.3390/molecules17089912
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