Photorhabdus asymbiotica is a gram‐negative bacterium that is not only as effective an insect pathogen as other members of the genus, but it also causes serious diseases in humans. The recently identified lectin PHL from P. asymbiotica verifiably modulates an immune response of humans and insects, which supports the idea that the lectin might play an important role in the host–pathogen interaction. Dimeric PHL contains up to seven l‐fucose‐specific binding sites per monomer, and in order to target multiple binding sites of PHL, α‐l‐fucoside‐containing di‐, tri‐ and tetravalent glycoclusters were synthesized. Methyl gallate and pentaerythritol were chosen as multivalent scaffolds, and the fucoclusters were built from the above‐mentioned cores by coupling with different oligoethylene bridges and propargyl α‐l‐fucosides using 1,3‐dipolar azide‐alkyne cycloaddition. The interaction between fucoside derivates and PHL was investigated by several biophysical and biological methods, ITC and SPR measurements, hemagglutination inhibition assay, and an investigation of bacterial aggregation properties were carried out. Moreover, details of the interaction between PHL and propargyl α‐l‐fucoside as a monomer unit were revealed using X‐ray crystallography. Besides this, the interaction with multivalent compounds was studied by NMR techniques. The newly synthesized multivalent fucoclusters proved to be up to several orders of magnitude better ligands than the natural ligand, l‐fucose.

中文翻译：

---

带有α-1-富尿嘧啶核苷的糖簇的合成及其与光生无形共生菌凝集素（PHL）相互作用的研究

非共生光杆菌是一种革兰氏阴性细菌，它不仅与该属的其他成员一样有效地成为昆虫病原体，而且还引起人类严重疾病。最近鉴定出的不对称假单胞菌中的凝集素PHL可确实调节人类和昆虫的免疫反应，这支持了以下观点：凝集素可能在宿主与病原体的相互作用中起重要作用。二聚体PHL每个单体最多包含七个l-岩藻糖特异性结合位点，为了靶向PHL的多个结合位点，α- 1合成了含有岩藻糖苷的二，三和四价糖簇。选择没食子酸甲酯和季戊四醇作为多价支架，并通过使用1,3-偶极叠氮化物-炔烃环加成反应，通过与不同的低聚乙烯桥和炔丙基α - 1岩藻糖苷偶联，从上述核心构建岩藻糖簇。岩藻糖苷衍生物与PHL之间的相互作用通过几种生物物理和生物学方法，ITC和SPR测量，血凝抑制试验以及细菌聚集特性的研究进行了研究。此外，有关PHL和炔丙基α- 1之间相互作用的详细信息岩藻糖苷作为单体单元通过X射线晶体学分析得以揭示。除此之外，还通过NMR技术研究了与多价化合物的相互作用。事实证明，新合成的多价fucoclusters的配体比天然配体l-岩藻糖高出几个数量级。