中文
Earlier issues
Announcement
More
Progress in Chemistry 2019, Vol. 31 Issue (7): 996-1006 DOI: 10.7536/PC190103 Previous Articles   Next Articles

New Materials for the Separation and Enrichment of N-Glycopeptides/Glycoproteins

Axin Liang1, Bo Tang1, Liquan Sun1, Xin Zhang1,2, Huipeng Hou1, Aiqin Luo1,*()   

  1. 1.School of Life Science, Beijing Institute of Technology, Beijing 100081, China
    2.School of Life Science and Technology, Nanyang Normal University, Nanyang 473061, China
  • Received: Online: Published:
  • Contact: Aiqin Luo
Richhtml ( 25 ) PDF ( 534 ) Cited
Export

EndNote

Ris

BibTeX

Protein glycosylation plays a crucial role in regulating various complex biological processes, such as molecular recognition, immune response, and protein folding. Since glycopeptides/glycoproteins are less abundant in complex biological samples or clinical samples, separation and enrichment of target proteins are often required before glycoproteomics analysis. Research and development of novel materials with high-efficiency glycoprotein separation and enrichment ability are of great significance for the study of glycoprotein/glycopeptide. In recent years, many new glycoprotein separation and enrichment materials have been reported, such as organic polymer materials, bio-based materials, new organic framework materials and new functional composite materials. Due to their structure, biocompatibility and physical and chemical properties, these materials have promoted the development of glycoprotein separation and enrichment technology from different levels. In this paper, the new materials related to the separation and enrichment of glycopeptide/glycoprotein at home and abroad are summarized and discussed, and the future development is proposed.

Key words: protein glycosylation, glycoprotein, glycopeptide, separation and enrichment, new material
Fig. 1 Fabrication routes of(a) benzene-1,3,5-tricarbohydrazide(BTZ),(b) 4,4'-(1,4-phenylene)-bis(1-phenylsemicarbazide)(BZ-PDI) and(c) polyacylsemicarbazide material(POP-1)[31]
Fig. 2 Synthesis of CS@PGMA@IDA[39]
Fig. 3 The procedure for enrichment and detection of the glycopeptides based on TpPa-1[52]
Fig. 4 Synthesis of SBA-15-SO3H[57]
Fig. 5 Procedure of the preparation of Cys-Mal@SiO2[58]
Fig. 6 Synthesis of Poly-Pro@SiO2[59]
Fig. 7 Schematic illustration of the synthetic procedure of Fe3O4@MPS@PMAC nanoparticles[66]
Fig. 8 Synthetic procedure for preparation of Fe3O4@PMAH core-shell magnetic nanocomposites[68]
[1]
Lu H J, Zhang Y, Yang P Y . Natl. Sci. Rev., 2016,3(3):345.
[2]
Zielinska D F, Gnad F, Wisniewski J R, Mann M . Cell, 2010,141:897.
[3]
Nilsson J, Ruetschi U, Halim A, Hesse C, Carlsohn E, Brinkmalm G . Nature Methods, 2009,6(11):809.
[4]
Zhang X H, Wang J W, He X W . ACS Appl. Mater. Interfaces, 2015,7:24576.
[5]
Chen C C, Su W C, Huang B Y, Chen Y J, Tai H C, Obena R P . Analyst, 2014,139(4):688.
[6]
Perego P, Gatti L, Beretta G L . Nat. Rev. Cancer, 2010,10:523.
[7]
Diop N K, Hrycyna C A . Biochemistry, 2005,44:5420.
[8]
Ohtsubo K, Marth J D . Cell, 2006,126:855.
[9]
Tsai P L, Chen S F . Mass Spectrom., 2017,6:S0064.
[10]
Zou X J, Jie J Z, Yang B . Chem. Commun., 2016,52:325.
[11]
Wu R Q, Li L T, Deng C H . Proteomics, 2016,16:1311.
[12]
Haltiwanger R S, Lowe J B . Annual Review of Biochemistry, 2004,73:491.
[13]
Ohta Y, Kameda K, Matsumoto M, Kawasaki N . Mass Spectrometry, 2017,6(1):A0061.
[14]
曹晶(Cao J), 聂爱英(Nie A Y), 陈瑶函(Chen Y H), 王胜(Wang S), 陆家杰(Lu J J), 杨芃原(Yang P Y), . 化学进展 (Progress in Chemistry), 2009,21(9):1888.
[15]
Shao W Y, Liang Y, Liang Z, Zhang L H, Zhang Y K . Journal of Instrumental Analysis, 2018,37(10):1212.
[16]
Zheng J N, Xiao Y, Wang L, Lin Z, Yang H H, Zhang L, Chen G A . J. Chromatogr. A, 2014,1358:29.
[17]
Zhang H, Li X J, Martin D B, Aebersold R . Nat. Biotechnol., 2003,21:660.
[18]
Liu L L, Yu M, Zhang Y, Wang C C, Lu H J . ACS Appl. Mater. Inter., 2014,6:7823.
[19]
Zhang L J, Jiang H C, Yao J, Wang Y L, Fang C Y, Yang P Y, Lu H J . Chem. Commun., 2014,50:1027.
[20]
Sun S S, Yang G L, Wang T, Wang Q Z, Chen C, Li Z . Anal. Bioanal. Chem., 2010,396:3071.
[21]
Wang Y L, Liu M B, Xie L Q, Fang C Y, Xiong H M, Lu H . Anal. Chem., 2014,86:2057.
[22]
Chen M, Lu Y, Ma Q, Guo L, Feng Y Q . Analyst, 2009,134:2158.
[23]
Qiu R Q, Regnier F E . Anal. Chem., 2005,77:2802.
[24]
Jin T, Xiong Z C, Zhu X . ACS Macro Lett., 2015,4:570.
[25]
Wang X, Liu Y, Ren L, Li H, Liu Z . Analytical Methods, 2013,5(20):5444.
[26]
Zheng J, Xiao Y, Wang L, Lin Z, Yang H, Zhang L . J. Chromatogr. A, 2014,1358:29.
[27]
Xu C, Xu K, Gu H, Zheng R, Liu H, Zhang X . Journal of the American Chemical Society, 2004,126(32):9938.
[28]
Zhao H, Li Y, Hu Y . Clinical Proteomics, 2014,11(1):21.
[29]
Bodnar E D, Perreault H . Analytical Chemistry, 2013,85(22):10895.
[30]
姜和(Jiang H), 付训忠(Fu X Z), 闵文杰(Min W J) . 重庆理工大学学报(自然科学)(Journal of Chongqing University of Technology)(Natural Science), 2012,26(03):23.
[31]
王红卫(Wang H W), 刘忠山(Liu Z S), 彭孝军(Peng X J), 欧俊杰(Ou J J), 叶明亮(Ye M L) . 色谱 (Chinese Journal of Chromatography), 2017,35(07):688.
[32]
Zhang J, Qi L, Zheng W T, Tian Y L, Chi A P, Zhang Z Q . Journal of Separation Science, 2017,40(5):1107.
[33]
Sun X, Dong J, Li J, Ye M, Zhang W, Ou J . J. Chromatogr, 2017,1489:72.
[34]
Azura A R, Misman M A . Solid State Phenomena, 2017,264:220.
[35]
吴秋惠(Wa Q H), 吴皓(Wu H), 王令充(Wang L C), 嵇晶(Ji J), 陈士勇(Chen S Y) . 中国新药杂志 (Chinese Journal of New Drugs), 2011,20(24):2430.
[36]
He X, Liang X, Chen X, Yuan B, Zhou P, Zhang L . Analytical Chemistry, 2017,89(18).
[37]
Sha Q Y, Wu Y K, Wang C, Sun B Y, Zhang Z H, Zhang L, Lin Y W, Liu X . J. Chromatogr. A, 2018,1569:8.
[38]
Liu Y J, Liu Y J, Dan Z, Zhang R Q, Li Z L . Analytical Chemistry, 2016,88(2):1067.
[39]
Zou X J, Jie J Z, Yang B . Chem. Commun., 2016,52:3251.
[40]
Xiao H, Chen W, Smeekens J M, Wu R . Nature Communications, 2018,9(1):1692.
[41]
Iqbal M S, Massey S, Akbar J, Ashraf C M, Masi, R . Food Chemistry, 2013,140(1/2):178.
[42]
Li S X, Deng N S, Qian S H, Huang G Q . Journal of Analytical Science, 2004,20(2):199.
[43]
Yang T, Cui Y N, Chen H Y, Li W H . Acta Chimica Sinica, 2017,75(4):339.
[44]
Paesani F . Chemical Society Reviews, 2003,32(5):276.
[45]
Ma W, Xu L N, Li X J . ACS Appl. Mater. Interfaces, 2017,9:19562.
[46]
Wang J, Li J, Wang Y, Gao M, Zhang X, Yang P . ACS Appl. Mater. Interfaces, 2016,8:27482.
[47]
Liu Q J, Xie Y Q, Deng C H, Li Y . Talanta, 2017,175:477.
[48]
Côté AP, Benin A I, Ockwig N W, O'Keeffe M, Matzger A J, Yaghi O M . Science, 2005,310(5751):1166.
[49]
El-Kaderi H M, Hunt J R, Mendoza-Cortes J L, Cote A P, Taylor R E, O″Keeffe M . Science, 2007,316(5822):268.
[50]
Feng X, Ding X, Jiang D . Chemical Society Reviews, 2012,41(18):6010.
[51]
Ding S Y, Wang W . Chemical Society Reviews, 2012,42(2):548.
[52]
Ma Y, Yuan F, Zhang X, Zhou Y, Zhang X . Analyst, 2017,142(17):3212.
[53]
Wang J, Li J, Gao M, Zhang X . Nanoscale, 2017,9(30):10750.
[54]
Huang G, Xiong Z, Qin H, Zhu J, Sun Z, Zhang Y . Analytica Chimica Acta, 2014,809:61.
[55]
Wu Z Y, Liang H W, Li C, Hu B C, Xu X X, Wang Q . Nano Research, 2014,7(12):1861.
[56]
Kresge C T, Leonowicz M E, Roth W J . Nature, 1992,359(6397):710.
[57]
Bibi A, Ju H X . Talanta, 2016,161:681.
[58]
Sun X, Zhang L, Zhang W . Se Pu, 2017,35(7):696.
[59]
姚要(Yao Y), 王宏喜(Wang H X), 卿光焱(Qing G Y), 孙涛垒(Sun T L) . 武汉理工大学学报 (Journal of Wuhan University of Technology), 2016,38(06):1.
[60]
Cao Y, Wen L, Svec F, Tan T, Lv Y . Chem. Eng. J., 2016,286:272.
[61]
Cao J, Xu J J, & Liu X G . J. Chromatogr. A, 2016,1468:86.
[62]
Kim D H, Guo Y, Zhang Z, Procissi D, Nicolai J, Omary R A . Adv. Healthc. Mater., 2014,3(5):714.
[63]
Peiris P M, Bauer L, Toy R . ACS Nano, 2012,6(5):4157.
[64]
Chen C, Wang S, Li L, Wang P, Chen C, Sun Z . Biomaterials, 2016,104:352.
[65]
Han L, Zhang Y, Zhang Y, Shu Y, Chen X W, Wang J H . Talanta, 2017,171:32.
[66]
Jiao F, Gao F, Wang H, Deng Y, Zhang Y, Qian X . Sci. Rep., 2017,7(6984):1.
[67]
Li Y, Wang J, Sun N, Deng C H . Anal. Chem. 2017,89:11151.
[68]
Liu L, Yu M, Zhang Y, Wang C, Lu H . ACS Appl. Mater. Inter., 2014,6(10):7823.
[69]
Krishnamoorthy L, Mahal L K . ACS Chemical Biology, 2009,4(9):715.
[70]
Zhang W, Liu W, Li P . Angewandte Chemie, 2015,53(46):12489.
[71]
Dube D H, Bertozzi C R . Nature Reviews Drug Discovery, 2005,4(6):477.
[72]
Ding X, Heiden P A . Macromolecular Materials & Engineering, 2014,299(3):268.
[73]
Xuan G S, Sun Q Y, Zheng X . Advanced Materials Research, 2014, 998-999:19.
[74]
Sellergren B, Martin-Esteban A . Molecularly Imprinted Polymers Elsevier, 2001.
[75]
Haupt K, Mosbach K . Chemical Reviews, 2000,100(7):2495.
[76]
Yoshimi Y . Ieej Transactions on Sensors & Micromachines, 2015,135(8):305.
[77]
Wulff G . Chemical Reviews, 2002,102(1):1.
[78]
Xing R, Wang S, Bie Z, He H, Liu Z . Nature Protocols, 2017,12(5):964.
[79]
Xie J, Zhong G, Cai C . Talanta, 2017,169:98.
[80]
Kasper E, Hanne D, Joseph L, Erik S R, Renato R, Benjamin H . Nutrients, 2018,10(6):751.
[81]
Li D, Tu T, Yang M, Xu C . Talanta, 2018,184:316.
[82]
Hunter T . Cell, 2000,100(1):113.
[83]
Olsen J V, Blagoev B, Gnad F, Macek B, Kumar C, Mortensen P . Cell, 2006,127(3):635.
[84]
Ohtsubo K, Marth J D . Cell, 2006,126(5):855.
[85]
Thingholm T E, Jensen O N, Larsen M R . Proteomics, 2009,9(6):1451.
[86]
Lin H Z, Yuan K P, Deng C H . Talanta, 2017,175:427.
[87]
Chen R, Wang F, Tan Y, Sun Z, Song C, Ye M . Journal of Proteomics, 2012,75(5):1666.
[88]
Mariño K, Bones J, Kattla J J, Rudd P M . Nature Chemical Biology, 2010,6(10):713.
[89]
Zhang Y, Kuang M, Zhang L, Yang P, Lu H . Analytical Chemistry, 2013,85(11):5535.
[90]
Mysling S, Palmisano G, HøJrup P, Thaysen-Andersen M . Analytical Chemistry, 2010,82(13):5598.
[91]
Neue K, Mormann M, Peter-Katalinić J, & Pohlentz G . J. Proteome Res, 2011,10:2248. 9a9ac33f-b7d7-4f78-8ec6-dec6b5c744fehttp://dx.doi.org/10.1021/pr101082c

doi: 10.1021/pr101082c
[92]
Yeh C H, Chen S H, Li D T, Lin H P, Huang H J, Chang C I . J. Chromatogr. A, 2012,1224(3):70.
[93]
Cao W, Huang J, Jiang B, Gao X, Yang P . Scientific Reports, 2016,6:29776.
[94]
Zhang M, Liu Y, Zhang D, Chen T, Li Z . Anal. Chem., 2017,89(15):8064.
[95]
包慧敏(Bao H M), 谢力琦(Xie L Q), 陆豪杰(Lu H J) . 色谱 (Chinese Journal of Chromatography), 2016,34(12):1145.
[1] Li Yin, Jianqiao Xu*, Zhoubing Huang, Guosheng Chen, Juan Zheng, Gangfeng Ouyang*. Solid-Phase Microextraction Fibers Based on Novel Materials:Preparation and Application [J]. Progress in Chemistry, 2017, 29(9): 1127-1141.
[2] Ding Peng, Chen Xian, Li Xiuling, Qing Guangyan, Sun Taolei, Liang Xinmiao. The Separation and Enrichment of Glycoproteins or Glycopeptides Based on Nanoparticles [J]. Progress in Chemistry, 2015, 27(11): 1628-1639.
[3] Luo Feng, Lin Zhijie, Chen Xi. Novel Materials and Approaches for Electrochemiluminescence Studies [J]. Progress in Chemistry, 2011, 23(12): 2588-2597.
[4] Wang Sheng, Zou Xia, Zhang Yan. Recent Advances in Mass Spectrometry Based Analysis of Protein O-glycosylation [J]. Progress in Chemistry, 2010, 22(12): 2428-2435.
[5] Cao Jing Nie Aiying Chen Yaohan Wang Sheng Lu Haojie Yang Pengyuan. Separation and Enrichment of Glycoproteins/Glycopeptides [J]. Progress in Chemistry, 2009, 21(09): 1888-1894.
[6]

Zhang Ying|Huang Linjuan|Wang Zhongfu**

. Techniques for Staining Glycoprotein on Gel Electrophoresis or Electroblotting [J]. Progress in Chemistry, 2008, 20(0708): 1158-1164.
[7] Liu Junhua1,2 Wang Fang1,2 Xu Xianlun1*. Oxidation of Alcohols into the Corresponding Aldehydes or Ketones by Molecular Oxygen [J]. Progress in Chemistry, 2007, 19(11): 1718-1726.
[8] Li Juan1,2 Zheng Jishen1 Shen Fei1 Fang Gemin1 Guo Qingxiang2 Liu Lei1,2**. Chemical Synthesis of Proteins [J]. Progress in Chemistry, 2007, 19(012): 1866-1882.
[9] Sun Xing-Quan,LI Jing,GENG Mei-Yu**,GUAN Hua-Shi. Analysis Techniques of Glycoprotein Glycan Structure for the Glycomics Study [J]. Progress in Chemistry, 2007, 19(01): 130-135.
[10] Qiang Ma1|Yong Ju1,2**|Yufen Zhao1. Chemical Synthesis of Glycoconjugates [J]. Progress in Chemistry, 2006, 18(09): 1110-1120.
[11] Fa Zhang Gang Liu . Solid-Phase Synthesis of Glycopeptides [J]. Progress in Chemistry, 2006, 18(05): 579-600.
[12] Ping Li 1,2,4 ,,Jianlin Zhang3 ,,Aiqin Wang1*. Progress in Analytical Chemistry of Chitosan and Its Derivatives [J]. Progress in Chemistry, 2006, 18(04): 467-473.
[13] Zhang Qingshan*,Guo Bingnan,Zhang Huimiao. Development and Application of Gemini Surfactants [J]. Progress in Chemistry, 2004, 16(03): 343-.
[14] Yan Zhe,Huang Junxiong. The Heterogeneity and Chroma tographic Purification of Glycoprote in Hormones [J]. Progress in Chemistry, 1999, 11(02): 163-.