title: Surface reactions of 4-aminothiophenol with heterobifunctional crosslinkers bearing both succinimidyl ester and maleimide for biomolecular immobilization.
abstract: Surface reactions of 4-aminothiophenol (4-ATP) with a series of heterogeneous crosslinkers containing both maleimide and succinimidyl ester groups were investigated with infrared reflection absorption spectroscopy (IRRAS) and X-ray photoelectron spectroscopy (XPS). Two types of surface reactions exist: (1) for most crosslinkers, a dominant reaction of amine and succinimidyl ester gave homogeneous maleimide-pendant surfaces; (2) for other crosslinkers, a side reaction between amine and maleimide, accompanying the main reaction, yielded heterogeneous surfaces with two linking groups, maleimide and succinimidyl ester. A typical example for the second case is the reaction of surface amines with N-succinimidyl-6-maleimidylhexanoate (SMH). Finally, a peptide, H-Gly-Arg-Gly-Asp-Ser-Pro-Cys-OH (GRGDSPC), was immobilized on the SMH-derived surface as a bridging structure through two linkages, cysteine thioether and glycine amide.
authors.affiliation: State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China. sjxiao@nju.edu.cn
authors.forename: Shou-Jun
authors.initials: SJ
authors.lastname: Xiao
authors.forename: Marco
authors.initials: M
authors.lastname: Wieland
authors.forename: Samuel
authors.initials: S
authors.lastname: Brunner
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D006046:Gold / Q000737:chemistry; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D010316:Particle Size; D010455:Peptides / Q000737:chemistry; D012680:Sensitivity and Specificity; D018629:Spectrometry, Mass, Secondary Ion / Q000379:methods; D013052:Spectrometry, X-Ray Emission / Q000379:methods; D013055:Spectrophotometry, Infrared / Q000379:methods; D013388:Succinimides / Q000737:chemistry*; D013438:Sulfhydryl Compounds; D013499:Surface Properties
chemical_list: D000814:Aniline Compounds; D003432:Cross-Linking Reagents; D004952:Esters; D008301:Maleimides; D010455:Peptides; D013388:Succinimides; D013438:Sulfhydryl Compounds; D006046:Gold; C064316:4-aminothiophenol