Carbohydrate and protein immobilization onto solid surfaces by sequential Diels-Alder and azide-alkyne cycloadditions.
We demonstrate the applicability of sequential Diels-Alder and azide-alkyne [3 + 2] cycloaddition reactions (click chemistry) for the immobilization of carbohydrates and proteins onto a solid surface. An alpha,omega-poly(ethylene glycol) (PEG) linker carrying alkyne and cyclodiene terminal groups was synthesized and immobilized onto an N-(epsilon-maleimidocaproyl) (EMC)-functionalized glass slide via an aqueous Diels-Alder reaction. In the process, an alkyne-terminated PEGylated surface was provided for the conjugation of azide-containing biomolecules via click chemistry, which proceeded to completion at low temperature and in aqueous solvent. As anticipated, alkyne, azide, cyclodiene, and EMC are independently stable and do not react with common organic reagents nor functional groups in biomolecules. Given an appropriate PEG linker, sequential Diels-Alder and azide-alkyne [3 + 2] cycloaddition reactions provide an effective strategy for the immobilization of a wide range of functionally complex substances onto solid surfaces.
Sun
Xue-Long
XL
Department of Surgery, Emory University, Atlanta, Georgia 30322, USA. xsun@emory.edu
Stabler
Cheryl L
CL
Cazalis
Chrystelle S
CS
Chaikof
Elliot L
EL
D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D001672:Biocompatible Materials / Q000737:chemistry*; D001710:Biotin / Q000737:chemistry*; D005898:Glass / Q000737:chemistry; D007785:Lactose / Q000737:chemistry*; D011092:Polyethylene Glycols / Q000737:chemistry*; D011485:Protein Binding; D013499:Surface Properties; D018180:Thrombomodulin / Q000737:chemistry*
D000480:Alkynes; D001386:Azides; D001672:Biocompatible Materials; D018180:Thrombomodulin; D011092:Polyethylene Glycols; D001710:Biotin; D007785:Lactose