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首页> 外文期刊>Bioorganic and Medicinal Chemistry >Lactotriaose-containing carbosilane dendrimers: Syntheses and lectin-binding activities
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Lactotriaose-containing carbosilane dendrimers: Syntheses and lectin-binding activities

机译：含乳三糖的碳硅烷树状大分子：合成和凝集素结合活性

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摘要

Carbosilane dendrimers periphery-functionalized with lactotriaose (GlcNAcβl-3Gaiβl—4Glc) with valencies of three, four, six, and twelve were prepared for use in a lectin-binding assay. A lactotriaose derivative was prepared from D-glucosamine and D-lactose derivatives. The N-Troc-protected glucosamine glycosyl donor and 3'-O-unprotected lactose glycosyl acceptor were condensed in the presence of silver trifluoromethanesulfonate and methylsulfenyl bromide to provide corresponding trisaccharide with new P-l-3 linkages in 92% yield. The protection group of the trisaccharide was transformed into an acetyl group. The 4-pen-tenyl glycoside was prepared from the acetate via glycosyl bromide. The alkene was converted into acetyl sulfide by addition of thio-acetic acid under radical conditions. The lactotriaose unit was linked with carbosilane dendrimers to afford acetyl-protected glycodendrimers. De-O-acetylation of the dendrimers was carried out in the presence of sodium methoxide and then aq NaOH to give the desired lactotriaose clusters using a carbosilane dendrimer backbone. Their biological activities toward WGA were evaluated by fluorescence methods. The binding constants of free lactotriaose and trivalent, tetravalent, hexavalent, and dodecavalent glycodendrimers to WGA were determined to be 1.1 × 10~3, 4.4 × 10~4, 5.1 × 10~4, 2.8 × 10~6, and 1.3 × 10~6 M~(-1), respectively. The hexavalent glycodendrimer showed a 2500-fold larger binding effect than that of free lactotriaose.
机译：准备用化三价，三价，四价，六价和十二价的经乳果糖（GlcNAcβ1-3Gaiβ1-4Glc）外围功能化的碳硅烷树状聚合物，以用于凝集素结合测定。从D-葡萄糖胺和D-乳糖衍生物制备乳三糖衍生物。 N-Troc保护的葡糖胺糖基供体和3'-O-未保护的乳糖糖基受体在三氟甲磺酸银和甲基亚磺酰基溴的存在下缩合，以92％的产率提供具有新的P-1-3键的相应三糖。三糖的保护基被转化为乙酰基。由乙酸酯经由糖基溴化物制备4-戊烯基糖苷。在自由基条件下，通过添加硫代乙酸，将烯烃转化为乙酰基硫化物。将乳三糖单元与碳硅烷树状聚合物连接，以提供乙酰基保护的糖树状聚合物。树枝状聚合物的脱-O-乙酰化反应在甲醇钠存在下，然后在NaOH水溶液中进行，使用碳硅烷树枝状聚合物主链得到所需的乳三糖簇。通过荧光方法评估了它们对WGA的生物学活性。游离乳果糖和三价，四价，六价和十二价糖树状聚合物与WGA的结合常数确定为1.1×10〜3、4.4×10〜4、5.1×10〜4、2.8×10〜6和1.3×10 〜6 M〜（-1）。六价糖树状聚合物显示的结合效果是游离乳三糖的2500倍。

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