稳定同位素标记多肽的合成及应用
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摘要
同位素稀释质谱法避免了基质效应和分析条件的影响,在定量分析和准确度方面具有特殊优势,在生物分子定量分析领域得到了普遍应用。稳定同位素标记肽段作为重要内标试剂广泛应用于蛋白质组学定量及食品过敏原检测。同位素稀释质谱技术的发展将会进一步推动稳定同位素标签技术在新药研发、临床病理、蛋白质组学、食品安全等领域的研究应用。本文从生物合成法和化学合成法方面综述了稳定同位素标记多肽的合成,并分别对细胞代谢标记法、高等真核生物标记法、酶催化标记法、乙酰化标记、标记氨基酸缩合法等合成方法进行了评述;同时介绍了稳定同位素标记多肽在乳制品检测、生物蛋白定量、蛋白测序及药物代谢、食品过敏原检测中的应用。
The isotope dilution mass spectrometry can avoid the matrix effect and the influence of analysis conditions,which has quantitative analysis and the accuracy of results in absolute precision special advantage,so it is widely applied in the field of quantitative analysis of biomolecules.The stable isotopic labeled peptides are widely used as an important internal standard reagent in the quantitative of proteomicsand food allergenic detection.The development of isotopic dilution mass spectrometry will further promote the research and application of stable isotope labeling technology in new drug development,clinical pathology,proteomics and food safety.With the rapid development of stable isotope labeling technology in recent years,the synthesis of stable isotope labeling peptides was summarized briefly from two aspects of biosynthesis method and chemical method.Methods of marker of cell metabolism,higher eukaryotes tag,enzyme catalytic notation,acetylation,labeled amino acid condensation were discussedin details.The application of stable isotopic marker polypeptide in the detection of dairy products,quantitative protein,protein sequencing and drug metabolism and food allergens were introduced.
The isotope dilution mass spectrometry can avoid the matrix effect and the influence of analysis conditions,which has quantitative analysis and the accuracy of results in absolute precision special advantage,so it is widely applied in the field of quantitative analysis of biomolecules.The stable isotopic labeled peptides are widely used as an important internal standard reagent in the quantitative of proteomicsand food allergenic detection.The development of isotopic dilution mass spectrometry will further promote the research and application of stable isotope labeling technology in new drug development,clinical pathology,proteomics and food safety.With the rapid development of stable isotope labeling technology in recent years,the synthesis of stable isotope labeling peptides was summarized briefly from two aspects of biosynthesis method and chemical method.Methods of marker of cell metabolism,higher eukaryotes tag,enzyme catalytic notation,acetylation,labeled amino acid condensation were discussedin details.The application of stable isotopic marker polypeptide in the detection of dairy products,quantitative protein,protein sequencing and drug metabolism and food allergens were introduced.
引文
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[5]侯捷,雷雯,杜晓宁.液相色谱-质谱联用法测定动物血浆中15 N标记氨基酸的同位素丰度[J].化学世界,2016(8):475-480.
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[8] Lanquar V,Kuhn L,Lelievre F,et al.15 Nmetabolic labeling for comparative plasma membrane proteomics in Arabidopsis cells[J].Proteomics,2007,7(5):750-754.
[9] Pan C,Oda Y,Lankford P K,et al.Characterization of anaerobic catabolism of p-coumarate in rhodopseudomonaspalustris by integrating transcriptomics and quantitative proteomics[J].Molecular&Cellular Proteomics,2008,7(5):938-948.
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[11]Phillip A,Thierry W,Christian L,et al.Production and application of high quality stable isotope-labeled human immunoglobulin G1for mass spectrometry analysis[J].Journal of Labelled Compounds&Radiopharmaceuticals,2017,60(3):160-167.
[12]Zinn N,Winter D,Lehmann W D.Recombinant isotope labeled and seleniumquantifiedproteinsfor absoluteproteinquantification[J].Analytical Chemistry,2010,82(6):2 334-2 340.
[13]Vidovic V,Prongidi-Fix L,Bechinger B,et al.Production and isotope labeling of antimicrobial peptides in Escherichia coli by means of a novel fusion partner that enables high-yield insoluble expression and fast purification[J].Journal of Peptide Science,2010,15(4):278-284.
[14]Liang S F,Yu Y B,Yang P Y,et al.Analysis of the protein complex associated with 14-3-3epsilon by a deuterated-leucine labeling quantitative proteomics strategy[J].Journal of Proteomics,2009,877(7):627-634.
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[16]李舒伟,先锋,侯桂雪,等.一种应用于定量蛋白质组学研究的稳定同位素标记肽段合成及定量新方法:中国,201510210493.6[P].2015-04-29.
[17]Krijgsveld J,Ketting R F,Mahmoudi T,et al.Metabolic labeling of C.elegans and D.melanogaster for quantitative proteomics[J].Nature Biotechnology,2003,21(8):927-931.
[18]Wu C C,Maccoss M J,Howell K E,et al.Metabolic labeling of mammalian organisms with stable isotopes for quantitative proteomic analysis[J].Analytical Chemistry,2004,76(17):4 951-4 959.
[19]Mylne J S,Craik D J.15 N-cyclotides by whole plant labeling[J].Peptide Science,2010,90(4):575-580.
[20]Foldynová-TrantírkováS,MatulováJ,D9tsch V,et al.A cost-effective amino-acid-type selective isotope labeling of proteins expressed in leishmaniatarentolae[J].Journal of Biomolecular Structure and Dynamics,2009,26(6):755-761.
[21]Desiderio D M,Kai M.Preparation of stable isotope incorporated peptide internal standards for field desorption mass spectrometry quantification of peptides in biologic tissue[J].Biomedical Mass Spectrometry,1983,10(8):471-479.
[22]Kristiansen T Z,Harsha H C,Grnborg M,et al.Differential membrane proteomics using 18 Olabeling to identify biomarkers for cholangiocarcinoma[J].Journal of Proteome Research 2008,7(11):4 670-4 677.
[23]Fenselau C,Yao X D.18O2-labeling in quantitative proteomic strategies:astatusreport[J].Journal of Proteome Research,2009,8(5):2 140-2 143.
[24]Bantscheff M,Schirle M,Sweetman G,et al.Quantitative mass spectrometry in proteomics:a critical review[J].Analytical&BioanalyticalChemistry,2007,389(4):1 017-1 031.
[25]Miyagi M,RaoK C S.Proteolytic O-18-labeling strategies for quantitative proteomics[J].Mass Spectrometry Reviews,2007,26(1):121-136.
[26]Staes A,Demol H,Van D J,et al.Global differential nongel proteomics by quantitative and stable labeling of tryptic peptides with oxygen-18[J].Journal Proteome Reseach,2004,3(4):786-791.
[27]Carreira R J,Rial R,Lopez-Ferrer.Ultrasonic energy as a new tool for fast isotopic 18 O labeling of proteins for mass spectrometry-based techniques:Preliminary results[J].Talanta,2008,76(2):400-406.
[28]李楠楠,周廉淇,毛心丽,等.18 O同位素标记定量肽段串联体蛋白质结合同位素稀释-多反应监测质谱的蛋白质绝对定量新方法[J].色谱,2013,31(6):522-530.Li Nannan,Zhou Lianqi,Mao Xinli,et al.A novel method for absolute protein quantification using 18 O isotope labeled concatamers of Q peptides combined with isotope dilution-multiple reaction monitoring mass spectrometry[J].Chinese Journal of Chromatography,2013,31(6):522-530(in Chinese).
[29]钱小红,刘慧玲,张养军.稳定同位素18 O标记蛋白质组双重定量方法与试剂盒:中国,200610146011.6[P].2006-11-03.
[30]Ji J,Chakraborty A,Geng M,et al.Strategy for qualitative and quantitative analysis in proteomics based on signature peptides[J].Journal of Chromatography B Biomedical Sciences&Applications,2000,745(1):197-210.
[31]Zhang H,Li X J,Martin D B,et al.Identification and quantification of N-linked glycoproteins using hydrazide chemistry,stable isotope labeling and mass spectrometry[J].Nature Biotechnology,2003,21(6):660-666.
[32]Hsu J L,Huang S Y,Chow N H,et al.Stableisotope dimethyl labeling for quantitative proteomics[J].Analytical Chemistry,2003,75(24),6 843-6 855.
[33]Boersema P,Aye T V T,Heck A,et al.Triplex protein quantification based on stable isotope labeling by peptide dimethylation applied to cell and tissue lysates[J].Proteomics,2008,8(22):4 624-4 632.
[34]Raijmakers R,Berkers C R,De J A,et al.Automated online sequential isotope labeling for protein quantitation applied to proteasome tissuespecific diversity[J].Molecular&Cellular Proteomics Mcp,2008,7(9):1 755-1 762.
[35]Breitung S T,Lopez J J,Dürner D,et al.A practical synthesis of the 13C/15 N-labelledtripeptide N-formyl-Met-Leu-Phe,useful as a reference in solid-state NMR spectroscopy[J].Beilstein Journal of Organic Chemistry,2008,4(1)35-38.
[36]Blankemeyer-Menge B,Nimtz M,Frank R.An efficient method for anchoring fmoc-anino acids to hydroxyl-functionalised solid supports[J].Tetrahedron Letters,1990,31(12):1 701-1 704.
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