Selective immobilization of peptides exclusively via N-terminus cysteines by water-driven reactions on surfaces.
Immobilizing peptides or proteins on bioinert surfaces enables the elucidation of ligand-receptor interaction in complex biological systems. Here, we report a highly chemoselective surface reaction that immobilizes peptides exclusively via N-terminus cysteine residue in a peptide. At pH 5.5, only N-terminus cysteines of peptides couple covalently with phenoxy amino squarate moieties presented on self-assembled monolayers (SAMs) of alkanethiols on gold films. The selectivity of this surface reaction can tolerate the presence of internal cysteines in close proximity to basic residues such as histidines. We demonstrated this selective surface reaction by mammalian cell adhesion and by SAMDI mass spectroscopy of the SAMs.
Sejwal
Preeti
P
Department of Chemistry, Syracuse Biomaterials Institute, Syracuse University, Syracuse, New York 13244, USA.
Narasimhan
Sri Kamesh
SK
Prashar
Deepali
D
Bandyopadhyay
Debjyoti
D
Luk
Yan-Yeung
YY
D000473:Alkanes / Q000737:chemistry; D000818:Animals; D002448:Cell Adhesion; D018929:Cell Culture Techniques / Q000295:instrumentation; D002621:Chemistry / Q000379:methods; D003545:Cysteine / Q000737:chemistry*; D006639:Histidine / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008670:Metals / Q000737:chemistry; D008956:Models, Chemical; D010455:Peptides / Q000737:chemistry*; D017434:Protein Structure, Tertiary; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013499:Surface Properties; D014867:Water / Q000737:chemistry*
D000473:Alkanes; D008670:Metals; D010455:Peptides; D013438:Sulfhydryl Compounds; D014867:Water; D006639:Histidine; D003545:Cysteine