A new bioorthogonal cross-linker with alkyne and hydrazide end groups for chemoselective ligation. Application to antibody labelling

作者：Fischer Durand Nathalie; Salmain Michele; Vessieres Anne^*; Jaouen Gerard

来源：Tetrahedron, 2012, 68(47): 9638-9644.

DOI：10.1016/j.tet.2012.09.062

• Immunoglobulin G
• Coumarin
• Fluorescent label
• Heterobifunctional cross-linker
• Bioorthogonal chemistry

We describe here the synthesis of the first bioorthogonal cross-linking reagent based on aminocaproic acid core with a hydrazide function at one end to react with glycoproteins and an alkyne group at the other end for Cu(I)-catalyzed click chemistry to azide-derivatized probes. As an application, this cross-linker was used to orthogonally conjugate profluorescent 3-azido-7-hydroxycoumarin to immunoglobulin G (IgG). An immunoassay showed that IgG was mostly not affected by the Cu(I)-catalyzed click chemistry conditions. Successful conjugations and retained immunoreactivity demonstrate the potential of this new bioorthogonal cross-linker in chemoselective ligation.

• 出版日期2012-11-25