Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and 'click' conjugation
Synthesis of multivalent Streptococcus suis adhesion inhibitors by enzymatic cleavage of polygalacturonic acid and 'click' conjugation
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DOI：
10.1039/b800283e
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发表时间：
2008-01-01
影响因子：
3.2
通讯作者：
Pieters, Roland J.
中科院分区：
文献类型：
--
作者：
Branderhorst, Hilbert M.;Kooij, Raymond;Pieters, Roland J.
通过聚半乳糖醛酸的有效果胶酶裂解和随后的化学官能团转化，合成了半乳糖二糖结构单元。除二糖外，还获得并修饰了相应的三糖。随后使用“点击”化学将这些化合物缀合至具有多达八个端基的树枝状聚合物。在血凝试验中，这些化合物被评估为病原体猪链球菌的粘附抑制剂，并且观察到四价和八价半乳糖化合物具有强烈的抑制作用，其 MIC 值在低纳摩尔范围内。相应的八价三糖是约。 20 倍弱的抑制剂。
A galabiose disaccharide building block was synthesized by an efficient pectinase cleavage of polygalacturonic acid and subsequent chemical functional group transformations. Besides the disaccharide, the corresponding trisaccharide was also obtained and modified. The compounds were subsequently conjugated to dendrimers with up to eight end groups using 'click' chemistry. The compounds were evaluated as inhibitors of adhesion of the pathogen Streptococcus suis in a hemagglutination assay and strong inhibition was observed for the tetra- and octavalent galabiose compound with MIC values in the low nanomolar range. The corresponding octavalent trisaccharide was a ca. 20-fold weaker inhibitor.