title: One-pot synthesis of phenylphosphonic acid imprinted polymers for tyrosine phosphopeptides recognition in aqueous phase.
abstract: The tyrosine phosphorylation of proteins plays a vital role in signal transduction pathways. The highly selective enrichment of tyrosine phosphopeptides remains a significant challenge in this area of research because of the low levels of tyrosine phosphorylation in cells. Herein, we report the development of a novel molecularly imprinted polymer (MIP)-based method for the recognition of tyrosine phosphopeptides in aqueous media using an epitope approach. Phenylphosphonic acid, which has been regarded the "epitope" of phosphotyrosine, was used as a template, and commercially available zinc acrylate was used as a functional monomer to prepare the MIP. The one-pot synthetic process was simple, efficient, and the resulting MIPs were low-cost, robust, and recyclable. The MIP demonstrated significant higher levels of adsorption capacity and selectivity for phenylphosphonic acid than the non-imprinting polymer (NIP) over its structural analog benzoic acid. The MIP was also used as a molecular receptor to recognize tyrosine phosphopeptides in aqueous media, and showed a clear preference for tyrosine phosphopeptides over interfering serine peptides compared to TiO2. These results revealed the feasibility of the use of MIPs to effectively mimic the epitope approach, and provided a promising alternative to the immunoaffinity techniques commonly used for capturing tyrosine phosphopeptides.
authors.affiliation: Department of Plant Nutrition, College of Resources and Environmental Sciences, China Agricultural University, Beijing, PR China.
authors.forename: Quishui
authors.initials: Q
authors.lastname: Li
authors.forename: Feng
authors.initials: F
authors.lastname: Shen
authors.forename: Xiao
authors.initials: X
authors.lastname: Zhang
authors.forename: Yufeng
authors.initials: Y
authors.lastname: Hu
authors.forename: Qingxi
authors.initials: Q
authors.lastname: Zhang
authors.forename: Lin
authors.initials: L
authors.lastname: Xu
authors.forename: Xueqin
authors.initials: X
authors.lastname: Ren
mesh_terms: D054802:Molecular Imprinting; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010748:Phosphopeptides / Q000032:analysis*; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D014443:Tyrosine / Q000737:chemistry / Q000378:metabolism; D014867:Water / Q000737:chemistry
chemical_list: D009943:Organophosphorus Compounds; D010748:Phosphopeptides; D011108:Polymers; D014867:Water; D014443:Tyrosine; C023604:phenylphosphonic acid
keywords: EGDMA; Epitope approach; IMAC; MOAC; Molecularly imprinted polymer; PEGD; Phenylphosphonic acid; Tyrosine phosphopeptides; ethylene glycol dimethacrylate; immobilized metal ion affinity chromatography; metal oxide affinity chromatography; pSer; pThr; pTyr; poly(ethylene glycol) diacrylate; serine phosphopeptides; threonine phosphopeptides; tyrosine phosphopeptides