糖蛋白质组学中基于化学反应的富集方法研究进展

doi:10.3724/SP.J.1123.2016.09003

摘要/Abstract

摘要：

蛋白质糖基化是一种广泛存在的重要的蛋白质翻译后修饰，糖基化肽在总酶解肽中占的比例不超过5%，这使得糖肽的分离富集成为糖蛋白质组学研究发展的关键技术之一。在诸多糖蛋白质组富集技术中，化学方法是富集技术的主导，本文从化学反应的角度介绍糖基化蛋白质富集的技术进展。富集过程按照连接和释放分别讨论，在连接过程中，重点介绍硼酸化学法、肼化学法、胺化学法和肟点击法；在释放过程中，以N-糖蛋白的酶释放法和O-糖蛋白的β-消除法为主导，一并介绍了最新的氧化断裂释放的化学法。最后，讨论总体富集策略的发展现状。该文以糖蛋白富集的共价反应为核心，分析不同方法的优缺点以及各技术在糖蛋白质组学研究中的应用和贡献。

关键词: 蛋白质糖基化, 富集, 共价反应, 连接/释放, 糖蛋白, 糖蛋白质组, 综述

Abstract:

Protein glycosylation is one of the most common and important post-translational modifications (PTMs) in mammalian cells. Glycopeptides usually exist at relatively low abundance (less than 5%) compared with non-glycosylated peptides. So, enrichment approaches are important for the analysis of glycoproteome. Approaches based on chemical reactions are the main trend, here we discuss them from chemical viewpoint. There are two main processes for enrichment of glycoproteins, glycoprotein conjugation and the release from solid phase. In conjugation process, we introduce four types of chemical reactions:one is boronic acid chemistry based on reaction between boronic acid and cis-diol groups on free glycans, and the other three are covalent reactions between aldehyde groups and functionalized groups, hydrazide for hydrazone ligation, alkylamine for reductive amination, aniline for nonreductive amination and aminooxy group for oxime click chemistry. In release process, N-glycosidase (PNGase) F for N-glycosylated proteins, β-elimination reaction for O-glycosylated proteins and a bleach method published recently are introduced, and the oxidative releasing of natural glycans is also introduced here. In addition, analysis strategies for N-/O-glycoproteins are discussed, including detection in glycoproteins and site-specific glycan occupancies. This review mainly focuses on the currently available chemical approaches based on covalent reactions for enrichment of glycoproteins, as well as new materials derivatized with different functional groups. We compare the advantages and disadvantages of different methods and try to evaluate the contribution and future trend based on authors viewpoint.

Key words: conjugation/release, covalent reaction, enrichment, glycoprotein, glycoproteome, protein glycosylation, review

中图分类号:

O658

包慧敏, 谢力琦, 陆豪杰. 糖蛋白质组学中基于化学反应的富集方法研究进展[J]. 色谱, 2016, 34(12): 1145-1153.

BAO Huimin, XIE Liqi, LU Haojie. Research advances of enrichment approaches based on chemical reactions in glycoproteomics[J]. Chinese Journal of Chromatography, 2016, 34(12): 1145-1153.

参考文献

[1] Ohtsubo K, Marth J D. Cell, 2006, 126:855
[2] Walsh G, Jefferis R. Nat Biotechnol, 2006, 24:1241
[3] Peracaula R, Barrab S, Sarrats A, et al. Dis Markers, 2008, 25(4/5):207
[4] Comunale M A, Lowman M, Long R E, et al. J Proteome Res, 2006, 5(2):308
[5] Johnson P J. J Gastroen Hepatol, 1999, 14:S32
[6] Drake R R, Schwegler E E, Malik G, et al. Mol Cell Proteomics, 2006, 5(10):1957
[7] Zhang S Z. Glycobiology and Biological Engineering. Beijing:Tsinghua University Press, 2002:97 张树政. 糖生物学和糖生物工程. 北京:清华大学出版社, 2002:97
[8] Haltiwanger R S, Lowe J B. Annu Rev Biochem, 2004, 73:491
[9] Kolli V, Schumacher K N, Dodds E D. Bioanalysis, 2015, 7:113
[10] Vosseller K, Trinidad J C, Chalkley R J, et al. Mol Cell Proteomics, 2006, 5:923
[11] Qiu R, Regnier F E. Anal Chem, 2005, 77:2802
[12] Comer F I, Vosseller K, Wells L, et al. Anal Biochem, 2001, 293:169
[13] Ball L E, Berkaw M N, Buse M G. Mol Cell Proteomics, 2006, 5:313
[14] Ding W, Hill J J, Kelly J. Anal Chem, 2007, 79:8891
[15] Zhao J, Simeone D M, Heidt D, et al. J Proteome Res, 2006, 5:1792
[16] Ongay S, Boichenko A, Govorukhina N, et al. J Sep Sci, 2012, 35:2341
[17] Liu X C. Chinese Journal of Chromatography, 2006, 24(1):73 刘小川. 色谱, 2006, 24(1):73
[18] Zhang L J, Xu Y W, Yao H L, et al. Chem-Eur J, 2009, 15:10158
[19] Wang Y L, Liu M B, Xie L Q, et al. Anal Chem, 2014, 86:2057
[20] Ma R N, Hu J J, Cai Z W, et al. Nanoscale, 2014, 6:3150
[21] Chen Y J, Xiong Z C, Zhang L Y, et al. Nanoscale, 2015, 7:3100
[22] Xu Y W, Wu Z X, Zhang L J, et al. Anal Chem, 2009, 81:503
[23] Liu L T, Zhang Y, Zhang L, et al. Anal Chim Acta, 2012, 753:64
[24] Wang H Y, Bie Z J, Lu C C, et al. Chem Sci, 2013, 4:4298
[25] Zhang Y T, Ma W F, Li D, et al. Small, 2014, 10:1379
[26] Li D J, Chen Y, Liu Z. Chem Soc Rev, 2015, 44:8097
[27] Pan X H, Chen Y, Zhao P X, et al. Angew Chem Int Ed, 2015, 54:6173
[28] Li H Y, Wang H Y, Liu Y C, et al. Chem Commun, 2012, 48:4115
[29] Ye J, Chen Y, Liu Z. Angew Chem Int Ed, 2014, 53:10386
[30] Cao J, Shen C P, Wang H, et al. J Proteome Res, 2009, 8:662
[31] Zhang H, Li X J, Martin D B, et al. Nat Biotechnol, 2003, 21:660
[32] Zou Z Q, Ibisate M, Zhou Y, et al. Anal Chem, 2008, 80:1228
[33] Tran T H, Park S Y, Lee H, et al. Analyst, 2012, 137:991
[34] Zhang L J, Jiang H C, Yao J, et al. Chem Commun, 2014, 50:1027
[35] Liu L T, Yu M, Zhang Y, et al. ACS Appl Mater Interfaces, 2014, 6:7823
[36] Sun B Y, Ranish J A, Utleg A G, et al. Mol Cell Proteomics, 2007, 6(1):141
[37] Wollscheid B, Bausch-Fluck D, Henderson C, et al. Nat Biotechnol, 2009, 27(4):378
[38] Nilsson J, Ruetschi U, Halim A, et al. Nat Methods, 2009, 6:809
[39] Klement E, Lipinszki Z, Kupihar Z, et al. J Proteome Res, 2010, 9:2200
[40] Abdel-Magid A F, Carson K G, Harris B D, et al. J Org Chem, 1996, 61:3849
[41] Zhang Y, Kuang M, Zhang L J, et al. Anal Chem, 2013, 85:5535
[42] Zhang Z, Sun D G, Cong Y T, et al. J Proteome Res, 2015, 14:3892
[43] Kaneshiro K, Fukuyama Y, Iwamoto S, et al. Anal Chem, 2011, 83:3663
[44] Snovida S I, Chen V C, Perreault H. Anal Chem, 2006, 78:8561
[45] Zhang Y, Yu M, Zhang C, et al. Chem Commun, 2015, 51:5982
[46] Pauloehrl T, Delaittre G, Bruns M, et al. Angew Chem Int Ed, 2012, 51:9181
[47] Nishimura S I, Niikura K, Kurogochi M, et al. Angew Chem Int Ed, 2005, 44:91
[48] Kurogochi M, Amano M, Fumoto M, et al. Angew Chem Int Ed, 2007, 46:8808
[49] Zeng Y, Ramya T N C, Dirksen A, et al. Nat Methods, 2009, 6:207
[50] Ramya T N C, Weerapana E, Cravatt B F, et al. Glycobiology, 2013, 23:211
[51] Zhang Y, Yu M, Zhang C, et al. Anal Chem, 2014, 86:7920
[52] Zhang W, Cao W Q, Huang J M, et al. Analyst, 2015, 140:1082
[53] Zhang W, Wang H, Tang H L, et al. Anal Chem, 2011, 83:4975
[54] Zhang W, Wang H, Zhang L, et al. Talanta, 2011, 85(1):499
[55] Zhao Y, Jia W, Wang J F. Anal Chem, 2011, 83:8802
[56] Jia W, Lu Z, Fu Y, et al. Mol Cell Proteomics, 2009, 8(5):913
[57] Llop E, Gallego R G, Belalcazar V, et al. Proteomics, 2007, 7(23):4278
[58] Harazono A, Kawasaki N, Itoh S, et al. Anal Biochem, 2006, 348(2):259
[59] Wells L, Vosseller K, Cole R N, et al. Mol Cell Proteomics, 2002, 1:791
[60] Zheng Y F, Guo Z H, Cai Z W. Talanta, 2009, 78:358
[61] Ashline D J, Yu Y, Lasanajak Y, et al. Mol Cell Proteomics, 2014, 13:2961
[62] Song X Z, Ju H, Lasanajak Y, et al. Nat Methods, 2016, 13(6):528
[63] Hawkins C L, Davies M J. Biochem J, 1998, 332:617
[64] Ohno N, Uchiyama M, Tsuzuki A, et al. Carbohydr Res, 1999, 316:161
[65] Rees M D, Hawkins C L, Davies M J, et al. J Am Chem Soc, 2003, 125:13719
[66] Rees M D, Davies M J. J Am Chem Soc, 2006, 128:3085
[67] Sparbier K, Wenzel T, Kostrzewa M. J Chromatogr B, 2006, 840:29
[68] Sun B Y, Ranish J A, Utleg A G, et al. Mol Cell Proteomics, 2007, 6:141
[69] Tian Y, Zhou Y, Elliott S, et al. Nat Protoc, 2007, 2:334
[70] Yang S, Li Y, Shah P, et al. Anal Chem, 2013, 85(11):5555
[71] Shah P, Yang S, Sun S S, et al. Anal Chem, 2013, 85(7):3606
[72] Yin B J, Gao Y, Chung C Y, et al. Biotechnol Bioeng, 2015, 112(11):2343
[73] Lin N, Mascarenhas J, Sealover N R, et al. Biotechnol Prog, 2015, 31(2):334
[74] Yang S, Wang M Y, Chen L J, et al. Scientific Reports, 2015, 5:17585
[75] Yang S, Yuan W, Yang W M, et al. Anal Chem, 2013, 85(17):8188
[76] Zhou Y, Aebersold R, Zhang H. Anal Chem, 2007, 79(15):5826
[77] Zou Z Q, Ibisate M, Zhou Y, et al. Anal Chem, 2008, 80(4):1228
[78] Sun S S, Shah P, Eshghi S T, et al. Nat Biotechol, 2016, 34:84
[79] Yang S J, Zhang H. Anal Chem, 2012, 84(5):2232
[80] Nilsson J, Ruetschi U, Halim A, et al. Nat Methods, 2009, 6:809
[81] Klement E, Lipinszki Z, Kupihar Z, et al. J Proteome Res, 2010, 9:2200
[82] Weng Y J, Sui Z G, Jiang H, et al. Scientific Reports, 2015, 5:9770
[83] Jiang H, Yuan H M, Qu Y Y, et al. Talanta, 2016, 146:225
[84] Wu C, Liang Yu, Zhao Q, et al. Chem-Eur J, 2014, 20(28):8737
[85] Liang Y, Wu C, Zhao Q, et al. Anal Chim Acta, 2015, 900:83
[86] Zielinska D F, Gnad F, Wisniewski J R, et al. Cell, 2010, 141:897
[87] Zhu J, Sun Z, Cheng K, et al. J Proteome Res, 2014, 13:1713

编辑推荐

Metrics

阅读次数

全文

HTML			PDF

最新录用	在线预览	正式出版	最新录用	在线预览	正式出版
0	0	0	0	0	79

	来源	本网站

	次数	79
	比例	100%

摘要

159

最新录用	在线预览	正式出版

0	0	159

	来源	本网站

	次数	159
	比例	100%