Peptide-Appended Permethylated β-Cyclodextrins with Hydrophilic and Hydrophobic Spacers,Bioconjugate Chemistry

当前位置： X-MOL 学术 › Bioconjugate Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Peptide-Appended Permethylated β-Cyclodextrins with Hydrophilic and Hydrophobic Spacers
Bioconjugate Chemistry ( IF 4.0 ) Pub Date : 2017-07-26 00:00:00 , DOI: 10.1021/acs.bioconjchem.7b00319
Abbas H. K. Al Temimi ₁ , Thomas J. Boltje ₁ , Daniel Zollinger _{2,

3} , Floris P. J. T. Rutjes ₁ , Martin C. Feiters ₁

Affiliation

A novel synthetic methodology, employing a combination of the strain-promoted azide–alkyne cycloaddition and maleimide–thiol reactions, for the preparation of permethylated β-cyclodextrin-linker-peptidyl conjugates is reported. Two different bifunctional maleimide cross-linking probes, the polyethylene glycol containing hydrophilic linker bicyclo[6.1.0] nonyne-maleimide and the hydrophobic 5′-dibenzoazacyclooctyne-maleimide, were attached to azide-appended permethylated β-cyclodextrin. The successfully introduced maleimide function was exploited to covalently graft a cysteine-containing peptide (Ac-Tyr-Arg-Cys-Amide) to produce the target conjugates. The final target compounds were isolated in high purity after purification by isocratic preparative reverse-phase high-performance liquid chromatography. This novel synthetic approach is expected to give access to many different cyclodextrin–linker peptides.

中文翻译：

带有疏水性和疏水性间隔基的肽附加的全甲基化β-环糊精

一种新的合成方法，采用张力促进叠氮化物-炔烃环加成和马来酰亚胺-硫醇反应的组合，对于全甲基化β的制备-环糊精-接头缀合物肽报道。将两种不同的双功能马来酰亚胺交联探针，即含有亲水性接头双环[6.1.0]壬炔-马来酰亚胺的聚乙二醇和疏水性5'-二苯并氮杂环辛炔-马来酰亚胺的疏水性探针连接到叠氮化物附加的全甲基化β-上。环糊精。利用成功引入的马来酰亚胺功能共价接枝含半胱氨酸的肽（Ac-Tyr-Arg-Cys-酰胺）以产生目标结合物。通过等度制备型反相高效液相色谱纯化后，高纯度分离出最终目标化合物。有望通过这种新颖的合成方法获得许多不同的环糊精-接头肽。

更新日期：2017-07-28

点击分享查看原文

点击收藏

公开下载

阅读更多本刊最新论文本刊介绍/投稿指南11