Anti-metastatic semi-synthetic sulfated maltotriose C-C linked dimers. Synthesis and characterisation.
Anti-metastatic semi-synthetic sulfated maltotriose C-C linked dimers. Synthesis and characterisation.
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DOI：
10.3390/molecules17089912
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发表时间：
2012-08-17
期刊：
影响因子：
--
通讯作者：
Torri G
中科院分区：
文献类型：
--
作者：
Vismara E;Coletti A;Valerio A;Naggi A;Urso E;Torri G
本文描述了半合成的硫酸化麦芽三糖C-C连接二聚体（SMTC）的制备和光谱表征，其中天然的C-O-C异头键被一个直接的中心C-C键取代。该C-C键相对于通常的异头键诱导构象和柔性变化。SMTC中性前体来自于麦芽三糖基溴化物通过麦芽三糖基自由基中间体二聚的电还原。新的C-C键构型（为方便起见，按天然异头键命名为α，β和β，β）决定了三种非对映异构体的统计比例形成。将它们通过硅胶快速色谱法，然后通过半制备型HPLC色谱法分离。将每种非对映异构体彻底硫酸化，得到相应的SMTC。SMTC是巨大的，其特征在于由NMR光谱，提供了硫酸化程度，太。发现α，α和α，β是具有高硫酸化程度（85-95%）的相当均匀的样品。β，β出现非均匀样品，其平均硫酸化程度评估为约78%。质谱实验证实了硫酸化程度范围。对SMTC的结构-生物学特性提出了一些思考。
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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影响因子：
--
作者：
Bendas G;Borsig L
通讯作者：
Borsig L
影响因子：
2.1
作者：
Al-Horani RA;Desai UR
通讯作者：
Desai UR
影响因子：
--
作者：
Casu B;Vlodavsky I;Sanderson RD
通讯作者：
Sanderson RD
影响因子：
15
作者：
de Paz, JL;Noti, C;Seeberger, PH
通讯作者：
Seeberger, PH
影响因子：
1.8
作者：
CARVER, JP
通讯作者：
CARVER, JP