An innovative and efficient route to the synthesis of metal-based glycoconjugates: proof-of-concept and potential applications
作者:Andrea Pettenuzzo、Diego Montagner、Patrick McArdle、Luca Ronconi
DOI:10.1039/c8dt01583j
日期:——
synthetic strategy was also successfully extended to other metal ions of biomedical interest, such as gold(I) and platinum(II), to obtain [AuI(SSC-Inp-GlcN)(PPh3)] and [PtII(SSC-Inp-GlcN)2], respectively. All compounds were fully characterized by elemental analysis, mid- and far-IR, mono- and multidimensional NMR spectroscopy, and, where possible, X-ray crystallography. Results and potential applications
为了开发更有效的策略来使金属药物与碳水化合物功能化,我们在此报告了一种创新而有效的合成途径,以高产率和纯度产生金(III)糖缀合物。该方法是基于锌(II)-二硫代氨基甲酸酯中间体[Zn II(SSC-Inp-GlcN)2 ](Inp =异烟交联部分; GlcN =氨基葡萄糖)的初始合成,然后将葡萄糖二氢吡啶二硫代氨基甲酸酯配体转移至金(III)中心经由所述锌(间金属转移反应II)中间体和K [金III溴4以1∶2的化学计量比,产生相应的葡萄糖官能化的金(III)-二硫代氨基甲酸酯衍生物[Au III Br 2(SSC-Inp-GlcN)]。不需要氨基葡萄糖支架的保护/去保护,也不需要色谱纯化。合成方案针对在C 2或C 6位置具有氨基功能的葡萄糖前体进行了优化,并且适用于α和β异构体。合成策略的应用也成功地扩展到其他具有生物医学意义的金属离子,例如金(I)和铂(II),以获得[Au I(SSC-Inp-GlcN)(PPh