Synthesis and characterization of oriented glyco-capturing macroligand.
An oriented glyco-capturing macroligand was synthesized by site-specific immobilization of an O-cyanate chain-end-functionalized boronic acid containing polymer (boropolymer) onto an amine surface. The O-cyanate chain-end-functionalized boropolymer was synthesized by arylamine-initiated cyanoxyl-mediated free-radical polymerization in a one-pot fashion. The chain-end O-cyanate was confirmed by (13)C NMR spectroscopy. The specific carbohydrate-binding capacity of the boropolymer was evaluated by an alizarin red S assay. Oriented and covalent immobilization of the O-cyanate chain-end-functionalized boropolymer onto the amine-modified solid surfaces and its specific glyco-capturing capacity were confirmed by the quartz crystal microbalance (QCM) and atomic force microscopy (AFM) techniques. The oriented multivalent glyco-capturing ligand can be used for efficient carbohydrate and glycoconjugate purification and identification, and thus is expected to constitute a core strategy of glycomics and glycoproteomics and carbohydrate-sensing applications.
Chalagalla
Srinivas
S
Department of Chemistry, Cleveland State University, Cleveland, OH 44115, USA.
Wang
Yanyang
Y
Ray
Dale
D
Zeng
Xiangqun
X
Perera
Indika
I
Sun
Xue-Long
XL
D001665:Binding Sites; D015374:Biosensing Techniques / Q000379:methods*; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry; D002241:Carbohydrates / Q000032:analysis*; D003485:Cyanates / Q000138:chemical synthesis / Q000737:chemistry*; D058105:Polymerization; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D058525:Quartz Crystal Microbalance Techniques / Q000379:methods*
D001896:Boron Compounds; D001897:Boronic Acids; D002241:Carbohydrates; D003485:Cyanates; D011108:Polymers