Dondoni Alessandro, Marra Alberto
Interdisciplinary Center for the Study of Inflammation, Università di Ferrara, Via Borsari 46, 44121 Ferrara, Italy.
Org Biomol Chem. 2017 Feb 21;15(7):1549-1553. doi: 10.1039/c6ob02458k. Epub 2017 Jan 24.
The Sulfur(vi) Fluoride Exchange (SuFEx), revived by Sharpless and co-workers from an unrecognized state, is an emerging new click reaction that is based on the high reactivity of sulfonyl fluorides and fluorosulfates with suitable nucleophiles such as silyl ethers and amines. Hence, we comment in this Perspective on the use of SuFEx for the synthesis of a new family of sugar containing sulfonamides from the reaction of a glycosylsulfonyl fluoride with aliphatic amines. We also highlight the applications of SuFEx to multivalent scaffolds such as tetraamino- and tetrafluorosulfonyl-calixarene leading to sulfonamide-linked sugar and iminosugar clusters. Finally, we report on the chemoselective functionalization of bovine serum albumin (BSA) which, owing to the amino group of lysine moieties, reacted with SOF to give a multivalent BSA-SOF system. The PEGylation of the same protein by coupling with a PEG-fluorosulfate is described as well.
由夏普莱斯及其同事从一种未被认可的状态复兴的六价硫氟交换反应（SuFEx），是一种新兴的点击反应，它基于磺酰氟和氟代硫酸盐与合适的亲核试剂（如硅醚和胺）的高反应活性。因此，我们在本综述中讨论了SuFEx在由糖基磺酰氟与脂肪族胺反应合成含磺酰胺的新型糖家族中的应用。我们还强调了SuFEx在多价支架（如四氨基和四氟磺酰基杯芳烃）上的应用，这些支架可生成磺酰胺连接的糖和亚氨基糖簇。最后，我们报道了牛血清白蛋白（BSA）的化学选择性功能化，由于赖氨酸部分的氨基，它与SOF反应生成多价BSA - SOF系统。同时还描述了通过与聚乙二醇 - 氟代硫酸盐偶联对同一蛋白质进行聚乙二醇化修饰的情况。
