Selective immobilization of peptides exclusively via N-terminus cysteines by water-driven reactions on surfaces

Preeti Sejwal, Sri Kamesh Narasimhan, Deepali Prashar, Debjyoti Bandyopadhyay, Yan Yeung Luk

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)6843-6846
Number of pages4
JournalJournal of Organic Chemistry
Volume74
Issue number17
DOIs
StatePublished - Sep 4 2009

ASJC Scopus subject areas

  • Organic Chemistry

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