Institut des Molécules et Matériaux du Mans (IMMM) UMR 6283 CNRS - Le Mans Université, Av. O. Messiaen, 72085 Le Mans cedex 9, France.
Org Biomol Chem. 2018 Oct 10;16(39):7124-7128. doi: 10.1039/c8ob01807c.
We report the efficient synthesis of a series of new azlactone-based heterofunctional linkers bearing two orthogonal clickable groups that proceed with full atom economy. These new linkers comprise an azlactone (oxazolone) group that quickly reacts with amino groups in biologically relevant medium without byproduct elimination and a (bio)orthogonal handle which further undergoes facile and selective click reactions such as thiol-ene coupling, Diels-Alder or azide-alkyne cycloadditions. As an example, the application of this methodology to lysozyme PEGylation in aqueous medium is described.
我们报告了一系列新型基于氮丙啶酮的杂功能连接子的高效合成，这些连接子带有两个正交的可点击基团，具有完全的原子经济性。这些新的连接子包含一个氮丙啶酮（恶唑啉酮）基团，它可以在生物相关的介质中快速与氨基反应，而不会产生副产物；还有一个（生物）正交的接头，它可以进一步进行简单和选择性的点击反应，如硫醇-烯加成、Diels-Alder 或叠氮-炔环加成。作为一个例子，本文描述了该方法在水相介质中溶菌酶 PEG 化中的应用。
