Abstract
Mass spectrometry (MS) is the most powerful tool in phosphoproteomics research. However, phosphopeptides usually are present in low concentrations and their preconcentration therefore is highly desired. We describe a two-step method for the synthesis of a metal organic framework of the type MIL-101(Cr) that is modified with urea (then designated as MIL-101(Cr)-UR2). It possesses large surface area, good solvent stability and high affinity for some phosphates. Due to the presence of modified urea functions, this material allows for selective and effective enrichment of phosphorylated peptides. It was successfully applied to the enrichment of phosphopeptides from non-fat-milk. The method was applied to the detection of phosphopeptides in a tryptic digest of β-casein where is showed a detection sensitivity as low as 10−10 M.
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References
Philippe PR, Pierre T (2013) The coming of age of phosphoproteomics-from large data sets to inference of protein functions. Mol Cell Proteomics 12:3453–3464
Pawson T, Scott JD (2005) Protein phosphorylation in signaling-50 years and counting. Trends Biochem Sci 30:286–290
Mann M, Ong SE, Gronborg M, Steen H, Jensen ON, Pandey A (2002) Analysis of protein phosphorylation using mass spectrometry: deciphering the phosphoproteome. Trends Biotechnol 20:261–268
Pawson T, Scott JD (1997) Signaling through scaffold, anchoring, and adaptor proteins. Science 278:2075–2080
Kailasa SK, Wu HF (2014) Recent developments in nanoparticle-based MALDI mass spectrometric analysis of phosphoproteomes. Microchim Acta 181:853–864
Leitner A, Sturm M, Hudecz O, Mazanek M, Smatt JH, Linden M, Lindner W, Mechtler K (2010) Probing the phosphoproteome of HeLa cells using Nanocast metal oxide microspheres for phosphopeptide enrichment. Anal Chem 82:2726–2733
Zeng YY, Chen HJ, Shiau KJ, Hung SU, Wang YS, Wu CC (2012) Efficient enrichment of phosphopeptides by magnetic TiO2-coated carbon-encapsulated iron nanoparticles. Proteomics 12:380–390
Batalha IL, Lowe CR, Roque AC (2012) Platforms for enrichment of phosphorylated proteins and peptides in proteomics. Trends Biotechnol 30:100–110
Thingholm TE, Jensen ON, Robinson PJ, Larsen MR (2008) SIMAC (sequential elution from IMAC), a phosphoproteomics strategy for the rapid separation of Monophosphorylated from multiply phosphorylated peptides. Mol Cell Proteomics 7:661–671
Xu L, Hu YF, Shen F, Li QS, Ren XQ (2013) Specific recognition of tyrosine-phosphorylated peptides by epitope imprinting of phenylphosphonic acid. J Chromatogr A 1293:85–91
Li QS, Shen F, Zhang X, Hu YF, Zhang QX, Xu L, Ren XQ (2013) One-pot synthesis of phenylphosphonic acid imprinted polymers for tyrosine phosphopeptides recognition in aqueous phase. Anal Chim Acta 795:82–87
Zhao M, Deng CH, Zhang XM (2014) The design and synthesis of a hydrophilic core–shell–shell structured magnetic metal–organic framework as a novel immobilized metal ion affinity platform for phosphoproteome research. Chem Commun 50:6228–6231
Zhu XY, Gu JL, Yang J, Wang Z, Li YS, Zhao LM, Zhao WR, Shi JL (2015) Zr-based metal–organic frameworks for specific and size-selective enrichment of phosphopeptides with simultaneous exclusion of proteins. J Mater Chem B 3:4242–4248
Xu LN, Li LP, Jin L, Bai Y, Liu HW (2014) Guanidyl-functionalized graphene as a bifunctional adsorbent for selective enrichment of phosphopeptides. Chem Commun 50:10963–10966
Xiong ZC, Chen YJ, Zhang LY, Ren J, Zhang QQ, Ye ML, Zhang WB, Zou HF (2014) Facile synthesis of guanidyl-functionalized magnetic polymer microspheres for tunable and specific capture of global phosphopeptides or only multiphosphopeptides. ACS Appl Mater Interfaces 6:22743–22750
Deng QL, Wu JH, Chen Y, Zhang ZJ, Wang Y, Fang GZ, Wang S, Zhang YK (2014) Guanidinium functionalized superparamagnetic silica spheres for selective enrichment of phosphopeptides and intact phosphoproteins from complex mixtures. J Mater Chem B 2:1048–1058
Emgenbroich M, Borrelli C, Shinde S, Lazraq I, Vilela F, Hall AJ, Oxelbark J, Lorenzi ED, Courtois J, Simanova A, Verhage J, Irgum K, Karim K, Sellergren B (2008) A Phosphotyrosine-imprinted polymer receptor for the recognition of tyrosine phosphorylated peptides. Chem Eur J 14:9516–9529
Chen J, Shinde S, Koch M-H, Eisenacher M, Galozzi S, Lerari T, Barkovits K, Subedi P, Krüger R, Kuhlmann K, Sellergren B, Helling S, Marcus K (2015) Low-bias phosphopeptide enrichment from scarce samples using plastic antibodies. Sci Rep 11438:1–12
Férey G (2008) Hybrid porous solids: past, present, future. Chem Soc Rev 37:191–214
Férey G, Mellot-Draznieks C, Serre C, Millange F (2005) Crystallized frameworks with Giant pores: are there limits to the possible? Acc Chem Res 38:217–225
Li JR, Sculley J, Zhou HC (2012) MetalOrganic frameworks for separations. Chem Rev 112:869–932
Gu ZY, Yang CX, Chang N, Yan XP (2012) Metal–organic frameworks for analytical chemistry: from sample collection to chromatographic separation. Acc Chem Res 45:734–745
Chen BL, Xiang SC, Qian GD (2010) Metal − organic frameworks with functional pores for recognition of small molecules. Acc Chem Res 43:1115–1124
Sonnauer A, Hoffmann F, Froba M, Kienle K, Duppel V, Thommes M, Serre C, Férey G, Stock N (2009) Giant pores in a chromium 2,6-Naphthalenedicarboxylate open-framework structure with MIL-101 topology. Angew Chem Int Ed 48:3791–3794
Wang Z, Cohen SM (2009) Postsynthetic modification of metal–organic frameworks. Chem Soc Rev 38:1315–1329
Cohen SM (2010) Modifying MOFs: new chemistry, new materials. Chem Sci 1:32–36
Luo XB, Ding L, Luo JM (2015) Adsorptive removal of Pb(II) ions from aqueous samples with amino-functionalization of metal–organic frameworks MIL-101(Cr). J Chem Eng Data 60:1732–1743
Bernt S, Guillerm V, Serreband C, Stock N (2011) Direct covalent post-synthetic chemical modification of Cr-MIL-101 using nitrating acid. Chem Commun 47:2838–2840
Lin YC, Kong CL, Chen L (2012) Direct synthesis of amine-functionalized MIL-101(Cr) nanoparticles and application for CO2 capture. RSC Adv 2:6417–6419
Chen YJ, Xiong ZC, Peng L, Gan YY, Zhao YM, Shen J, Qian JH, Zhang LY, Zhang WB (2015) Facile preparation of Core − Shell magnetic metal − organic framework nanoparticles for the selective capture of phosphopeptides. Appl Mater Interfaces 7:16338–16347
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The financial support from Tianjin Research Program of Application Foundation and Advanced Technology (15JCYBJC23800) is gratefully acknowledged.
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Yang, X., Xia, Y. Urea-modified metal-organic framework of type MIL-101(Cr) for the preconcentration of phosphorylated peptides. Microchim Acta 183, 2235–2240 (2016). https://doi.org/10.1007/s00604-016-1860-1
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DOI: https://doi.org/10.1007/s00604-016-1860-1