SuFEx: a metal-free click ligation for multivalent biomolecules

被引:38
作者
Dondoni, Alessandro [1 ]
Marra, Alberto [2 ]
机构
[1] Univ Ferrara, Interdisciplinary Ctr Study Inflammat, Via Borsari 46, I-44121 Ferrara, Italy
[2] Univ Montpellier, Ecole Natl Super Chim Montpellier, IBMM, UMR 5247,CNRS, 8 Rue Ecole Normale, F-34296 Montpellier 5, France
关键词
AZIDE-ALKYNE CYCLOADDITION; THERAPEUTIC PROTEINS; TERMINAL ALKYNES; SILYL ETHERS; CHEMISTRY; GLYCOCALIXARENES; RECOGNITION; INHIBITION; FLUORIDE; SURFACE;
D O I
10.1039/c6ob02458k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 fluoro-sulfates 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 SO2F2 to give a multivalent BSA-SO2F system. The PEGylation of the same protein by coupling with a PEG-fluorosulfate is described as well.
引用
收藏
页码:1549 / 1553
页数:5
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