活性多肽序列结构分析鉴定技术的研究进展
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摘要
为了较全面地掌握多肽序列测定技术相关研究的最新发展,调研了近年来活性多肽序列分析、鉴定的相关文献,从经典的N端序列测定、质谱法机理研究、质谱法与软电离技术联用、核磁共振法等方面,对多肽序列测定技术的最新进展进行了综述,着重阐述4种软电离技术与质谱法的结合及应用。
In order to master the up- to- date research progress of the technology related to the identification of bioactive polypeptides,this review was about the new breakthroughs and achievements of various technologies which were subjected to identify and analyze bioactive polypeptides in recent years on the aspect of the new development of the N- terminal sequence determination technology,the mass spectrometry combined with soft ionization technologies and the nuclear magnetic resonance spectroscopy,as well as the mechanism study on mass spectrometry. And it focused on the application of new combination of the four soft ionization technologies and mass spectrometry. Upon these progresses,it expected an innovation based on some traditional pathway to break through the bottleneck of recent polypeptides studying and a further improvement in the polypeptides researches as well as the proteomics.
In order to master the up- to- date research progress of the technology related to the identification of bioactive polypeptides,this review was about the new breakthroughs and achievements of various technologies which were subjected to identify and analyze bioactive polypeptides in recent years on the aspect of the new development of the N- terminal sequence determination technology,the mass spectrometry combined with soft ionization technologies and the nuclear magnetic resonance spectroscopy,as well as the mechanism study on mass spectrometry. And it focused on the application of new combination of the four soft ionization technologies and mass spectrometry. Upon these progresses,it expected an innovation based on some traditional pathway to break through the bottleneck of recent polypeptides studying and a further improvement in the polypeptides researches as well as the proteomics.
引文
[1]D D Kitts,K Weiler.Bioactive proteins and peptides from food sources.Applications of bioprocesses used in isolation and recovery[J].Current Pharmaceutical Design,2003,9(16):1309-1323.
[2]P Edman.A method for the determination of amino acid sequence in peptides[J].Archives of Biochemistry,1949,22(3):475.
[3]V Gavrilov,A Frank-Kamenetskiǐ,M Frank-Kamenetskiǐ.The problem of amino acid sequence determination in polypeptides by mass spectrum of its fragments[J].Biokhimiia(Moscow,Russia),1965,31(4):799-804.
[4]A Geddes,G Graham,H Morris.Mass-spectrometric determination of the amino acid sequences in peptides isolated from protein silk fibroin of Bombyx mori[J].Biochem.J,1969,114:695-702.
[5]H K Wipf,P Irving,M Mccamish,et al.Mass spectrometric studies of peptides.V.Determination of amino acid sequences in peptide mixtures by mass spectrometry[J].Journal of the American Chemical Society,1973,95(10):3369-3375.
[6]H R Morris,A Dell.Mass-spectrometric identification and sequence location of the ten residues of the new amino acid(gamma-Carboxyglutamic acid)in the N-terminal region of prothrombin[J].Biochem.J,1976,153:663-679.
[7]M Powell,P Tempst.Microflow-based automated chemistries:application to protein sequencing[J].Analytical Chemistry,2001,73(4):776-786.
[8]孙敬敬,刘慧慧,周世权,等.一种新型贻贝抗菌肽的分离纯化及鉴定[J].水生生物学报,2014,38(3):563-570.
[9]李妍妍,戴娟,胡玲萍,等.仿刺参(Apostichopus japonicus)和海地瓜(Acaudina leucoprocta)体壁多肽的响应面法酶解和N末端测序[J].海洋与湖沼,2015,(3):620-627.
[10]Y Perez-Riverol,A S Nchez,Y Ramos,et al.In silico analysis of accurate proteomics,complemented by selective isolation of peptides[J].Journal of Proteomics,2011,74(10):2071-2082.
[11]X A He,N Washburn,E Arevalo,et al.Analytical characterization of Ig G Fc subclass variants through high-resolution separation combined with multiple LC-MS identification[J].Analytical and Bioanalytical Chemistry,2015,407(23):7055-7066.
[12]张鹏军.碱性氨基酸在多肽质谱断裂中作用机理的研究[D].济南:山东大学,2012.
[13]汪兵.金属—肽段复合物在质谱中碎裂规律的研究[D].长春:吉林大学,2013.
[14]李华梅.基于正反库特征信息匹配的蛋白质二级质谱鉴定算法[D].昆明:云南民族大学,2015.
[15]王梅杰.酸性氨基酸在多肽质谱裂解中作用的研究[D].济南:山东大学,2012.
[16]孙秋实.基于串联质谱数据的蛋白质—基因组学方法研究[D].北京:北京交通大学,2015.
[17]张森,倪彧,李树奇,等.适用小分子化合物MALDI分析的基质研究[J].化学进展,2013,26(01):158-166.
[18]H R Morris,M Panico,M Barber,et al.Fast atom bombardment:a new mass spectrometric method for peptide sequence analysis[J].Biochemical and Biophysical Research Communications,1981,101(2):623-631.
[19]俞振培,贺晓然.FAB质谱法研究肽的氨基酸序列[J].北京大学学报:自然科学版,1994,30(4):398-402.
[20]杨芬,贺玖明,张瑞萍,等.快原子轰击离子化质谱研究酚类化合物抗氧化作用[J].分析化学,2015,43(02):233-238.
[21]贾辰熙.综合质谱法对生物活性多肽解析表征的研究[D].天津:天津大学,2010.
[22]M Dupr,S Cantel,J Martinez,et al.Occurrence of C-terminal residue exclusion in peptide fragmentation by ESI and MALDI tandem mass spectrometry[J].Journal of the American Society for Mass Spectrometry,2012,23(2):330-346.
[23]王慧心.钠离子化肽在电喷雾质谱低能量碰撞下碎裂规律的研究[D].长春:吉林大学,2015.
[24]刘丹.秋刀鱼蛋白抗氧化肽的分离纯化及其抗疲劳功效研究[D].广州:华南理工大学,2015.
[25]于志鹏.蛋清源活性肽的结构鉴定及生物活性研究[D].长春:吉林大学,2014.
[26]R Aebersold,M Mann.Mass spectrometry-based proteomics[J].Nature,2003,422(6928):198-207.
[27]L Yang,S Kazuyuki,S Masahiko,et al.Increased concentrations of apo A-I and apo A-II fragments in the serum of patients with hepatocellular carcinoma by magnetic beads-assisted MALDITOF mass spectrometry[J].American Journal of Clinical Pathology,2014,141(1):.
[28]X Ding,X Zhan,X Yuan,et al.Microfabricated glow discharge plasma(MFGDP)for ambient desorption/ionization mass spectrometry[J].Analytical Chemistry,2013,85(19):9013-9020.
[29]X Ding,Y Duan.Plasma-based ambient mass spectrometry techniques:the current status and future prospective[J].Mass Spectrometry Reviews,2015,34(4):449-473.
[30]B Nilsson,N Norden,S Svensson.Structural studies on the carbohydrate portion of fetuin[J].Journal of Biological Chemistry,1979,254(11):4545-4553.
[31]W L Russell,R C Pandey,C P Schaffner,et al.Crisamicin C,a new isochromanequinone antibiotic.Isolation,structure determination,and biosynthesis[J].The Journal of Antibiotics,1988,41(2):149-156.
[32]G J Feistner,P H Jrup,C J Evans,et al.Mass spectrometric charting of bovine posterior/intermediate pituitary peptides[J].Proceedings of the National Academy of Sciences,1989,86(16):6013-6017.
[33]A Tsarbopoulos.Plasma desorption mass spectrometry of natural and recombinant peptides and proteins[J].Peptide Research,1988,2(4):258-266.
[34]P Schindler,F Bitsch,K Klarskov,et al.Cuttlefish sperm protamines[J].European Journal of Biochemistry,1991,195(3):621-629.
[35]J-M Schmitter.Performances and limits of plasma desorption mass spectrometry in the primary structure determination of proteins[J].Journal of Chromatography A,1991,557:359-368.
[36]A Tsarbopoulos,M Karas,K Strupat,et al.Comparative mapping of recombinant proteins and glycoproteins by plasma desorption and matrix-assisted laser desorption/ionization mass spectrometry[J].Analytical Chemistry,1994,66(13):2062-2070.
[37]H H Rasmussen,E M Rtz,M Mann,et al.Identification of transformation sensitive proteins recorded in human two-dimensional gel protein databases by mass spectrometric peptide mapping alone and in combination with microsequencing[J].Electrophoresis,1994,15(1):406-416.
[38]E Pittenauer,J C Quintela,E R Schmid,et al.Characterization of braun’s lipoprotein and determination of its attachment sites to peptidoglycan by 252Cf-PD and MALDI time-of-flight mass spectrometry[J].Journal of the American Society for Mass Spectrometry,1995,6(10):892-905.
[39]N Reztsova,M Kulish,A Mironov.Plasma-desorption mass spectrometry of natural compounds.1.Basic properties of the method and its use for analyzing proteins and peptides[J].Bioorganicheskaia Khimiia,1996,22(1):3-13.
[40]F P O'Harte,P H Jrup,C R Barnett,et al.Identification of the site of glycation of human insulin[J].Peptides,1996,17(8):1323-1330.
[41]A Tsarbopoulos,J Varnerin,S Cannon-Carlson,et al.Mass spectrometric mapping of disulfide bonds in recombinant human interleukin-13[J].Journal of Mass Spectrometry,2000,35(3):446-453.
[42]丁薛璐,段忆翔.等离子体常压解吸离子源质谱[J].中国科学:化学,2014,33(05):672-679.
[43]苏明扬,侯可勇,黄泽健,等.非接触热解析封闭式低温等离子体电离源质谱法快速分析3种农药残留[J].分析化学,2014,42(3):384-389.
[44]万同青.微波等离子体炬离子化源的构建及其应用基础研究[D].杭州:浙江大学,2011.
[45]张体强,金伟,周建光,等.微波等离子体常压解吸电离质谱法快速检测化学药剂中的活性成分[J].高等学校化学学报,2012,33(9):1938-1944.
[46]B B Carstens,K J Rosengren,S Gunasekera,et al.Isolation,characterization,and synthesis of the barrettides:Disulfide-containing peptides from the marine sponge Geodia barretti[J].Journal of Natural Products,2015,78(8):1886-1893.
[47]刘源,马垒,仇春泱,等.热加工暗纹东方鲀肌肉中呈味肽分离鉴定及呈味特性研究[J].现代食品科技,2016,32(03):1-9.
[48]解铭,侯虎,张姝妹,等.鳕鱼酶解液苦味肽的纯化鉴定[J].现代食品科技,2016,32(02):1-8.
[49]刘琳.功能性食品中多肽的分离分析方法研究[D].泰安:山东农业大学,2013.
[2]P Edman.A method for the determination of amino acid sequence in peptides[J].Archives of Biochemistry,1949,22(3):475.
[3]V Gavrilov,A Frank-Kamenetskiǐ,M Frank-Kamenetskiǐ.The problem of amino acid sequence determination in polypeptides by mass spectrum of its fragments[J].Biokhimiia(Moscow,Russia),1965,31(4):799-804.
[4]A Geddes,G Graham,H Morris.Mass-spectrometric determination of the amino acid sequences in peptides isolated from protein silk fibroin of Bombyx mori[J].Biochem.J,1969,114:695-702.
[5]H K Wipf,P Irving,M Mccamish,et al.Mass spectrometric studies of peptides.V.Determination of amino acid sequences in peptide mixtures by mass spectrometry[J].Journal of the American Chemical Society,1973,95(10):3369-3375.
[6]H R Morris,A Dell.Mass-spectrometric identification and sequence location of the ten residues of the new amino acid(gamma-Carboxyglutamic acid)in the N-terminal region of prothrombin[J].Biochem.J,1976,153:663-679.
[7]M Powell,P Tempst.Microflow-based automated chemistries:application to protein sequencing[J].Analytical Chemistry,2001,73(4):776-786.
[8]孙敬敬,刘慧慧,周世权,等.一种新型贻贝抗菌肽的分离纯化及鉴定[J].水生生物学报,2014,38(3):563-570.
[9]李妍妍,戴娟,胡玲萍,等.仿刺参(Apostichopus japonicus)和海地瓜(Acaudina leucoprocta)体壁多肽的响应面法酶解和N末端测序[J].海洋与湖沼,2015,(3):620-627.
[10]Y Perez-Riverol,A S Nchez,Y Ramos,et al.In silico analysis of accurate proteomics,complemented by selective isolation of peptides[J].Journal of Proteomics,2011,74(10):2071-2082.
[11]X A He,N Washburn,E Arevalo,et al.Analytical characterization of Ig G Fc subclass variants through high-resolution separation combined with multiple LC-MS identification[J].Analytical and Bioanalytical Chemistry,2015,407(23):7055-7066.
[12]张鹏军.碱性氨基酸在多肽质谱断裂中作用机理的研究[D].济南:山东大学,2012.
[13]汪兵.金属—肽段复合物在质谱中碎裂规律的研究[D].长春:吉林大学,2013.
[14]李华梅.基于正反库特征信息匹配的蛋白质二级质谱鉴定算法[D].昆明:云南民族大学,2015.
[15]王梅杰.酸性氨基酸在多肽质谱裂解中作用的研究[D].济南:山东大学,2012.
[16]孙秋实.基于串联质谱数据的蛋白质—基因组学方法研究[D].北京:北京交通大学,2015.
[17]张森,倪彧,李树奇,等.适用小分子化合物MALDI分析的基质研究[J].化学进展,2013,26(01):158-166.
[18]H R Morris,M Panico,M Barber,et al.Fast atom bombardment:a new mass spectrometric method for peptide sequence analysis[J].Biochemical and Biophysical Research Communications,1981,101(2):623-631.
[19]俞振培,贺晓然.FAB质谱法研究肽的氨基酸序列[J].北京大学学报:自然科学版,1994,30(4):398-402.
[20]杨芬,贺玖明,张瑞萍,等.快原子轰击离子化质谱研究酚类化合物抗氧化作用[J].分析化学,2015,43(02):233-238.
[21]贾辰熙.综合质谱法对生物活性多肽解析表征的研究[D].天津:天津大学,2010.
[22]M Dupr,S Cantel,J Martinez,et al.Occurrence of C-terminal residue exclusion in peptide fragmentation by ESI and MALDI tandem mass spectrometry[J].Journal of the American Society for Mass Spectrometry,2012,23(2):330-346.
[23]王慧心.钠离子化肽在电喷雾质谱低能量碰撞下碎裂规律的研究[D].长春:吉林大学,2015.
[24]刘丹.秋刀鱼蛋白抗氧化肽的分离纯化及其抗疲劳功效研究[D].广州:华南理工大学,2015.
[25]于志鹏.蛋清源活性肽的结构鉴定及生物活性研究[D].长春:吉林大学,2014.
[26]R Aebersold,M Mann.Mass spectrometry-based proteomics[J].Nature,2003,422(6928):198-207.
[27]L Yang,S Kazuyuki,S Masahiko,et al.Increased concentrations of apo A-I and apo A-II fragments in the serum of patients with hepatocellular carcinoma by magnetic beads-assisted MALDITOF mass spectrometry[J].American Journal of Clinical Pathology,2014,141(1):.
[28]X Ding,X Zhan,X Yuan,et al.Microfabricated glow discharge plasma(MFGDP)for ambient desorption/ionization mass spectrometry[J].Analytical Chemistry,2013,85(19):9013-9020.
[29]X Ding,Y Duan.Plasma-based ambient mass spectrometry techniques:the current status and future prospective[J].Mass Spectrometry Reviews,2015,34(4):449-473.
[30]B Nilsson,N Norden,S Svensson.Structural studies on the carbohydrate portion of fetuin[J].Journal of Biological Chemistry,1979,254(11):4545-4553.
[31]W L Russell,R C Pandey,C P Schaffner,et al.Crisamicin C,a new isochromanequinone antibiotic.Isolation,structure determination,and biosynthesis[J].The Journal of Antibiotics,1988,41(2):149-156.
[32]G J Feistner,P H Jrup,C J Evans,et al.Mass spectrometric charting of bovine posterior/intermediate pituitary peptides[J].Proceedings of the National Academy of Sciences,1989,86(16):6013-6017.
[33]A Tsarbopoulos.Plasma desorption mass spectrometry of natural and recombinant peptides and proteins[J].Peptide Research,1988,2(4):258-266.
[34]P Schindler,F Bitsch,K Klarskov,et al.Cuttlefish sperm protamines[J].European Journal of Biochemistry,1991,195(3):621-629.
[35]J-M Schmitter.Performances and limits of plasma desorption mass spectrometry in the primary structure determination of proteins[J].Journal of Chromatography A,1991,557:359-368.
[36]A Tsarbopoulos,M Karas,K Strupat,et al.Comparative mapping of recombinant proteins and glycoproteins by plasma desorption and matrix-assisted laser desorption/ionization mass spectrometry[J].Analytical Chemistry,1994,66(13):2062-2070.
[37]H H Rasmussen,E M Rtz,M Mann,et al.Identification of transformation sensitive proteins recorded in human two-dimensional gel protein databases by mass spectrometric peptide mapping alone and in combination with microsequencing[J].Electrophoresis,1994,15(1):406-416.
[38]E Pittenauer,J C Quintela,E R Schmid,et al.Characterization of braun’s lipoprotein and determination of its attachment sites to peptidoglycan by 252Cf-PD and MALDI time-of-flight mass spectrometry[J].Journal of the American Society for Mass Spectrometry,1995,6(10):892-905.
[39]N Reztsova,M Kulish,A Mironov.Plasma-desorption mass spectrometry of natural compounds.1.Basic properties of the method and its use for analyzing proteins and peptides[J].Bioorganicheskaia Khimiia,1996,22(1):3-13.
[40]F P O'Harte,P H Jrup,C R Barnett,et al.Identification of the site of glycation of human insulin[J].Peptides,1996,17(8):1323-1330.
[41]A Tsarbopoulos,J Varnerin,S Cannon-Carlson,et al.Mass spectrometric mapping of disulfide bonds in recombinant human interleukin-13[J].Journal of Mass Spectrometry,2000,35(3):446-453.
[42]丁薛璐,段忆翔.等离子体常压解吸离子源质谱[J].中国科学:化学,2014,33(05):672-679.
[43]苏明扬,侯可勇,黄泽健,等.非接触热解析封闭式低温等离子体电离源质谱法快速分析3种农药残留[J].分析化学,2014,42(3):384-389.
[44]万同青.微波等离子体炬离子化源的构建及其应用基础研究[D].杭州:浙江大学,2011.
[45]张体强,金伟,周建光,等.微波等离子体常压解吸电离质谱法快速检测化学药剂中的活性成分[J].高等学校化学学报,2012,33(9):1938-1944.
[46]B B Carstens,K J Rosengren,S Gunasekera,et al.Isolation,characterization,and synthesis of the barrettides:Disulfide-containing peptides from the marine sponge Geodia barretti[J].Journal of Natural Products,2015,78(8):1886-1893.
[47]刘源,马垒,仇春泱,等.热加工暗纹东方鲀肌肉中呈味肽分离鉴定及呈味特性研究[J].现代食品科技,2016,32(03):1-9.
[48]解铭,侯虎,张姝妹,等.鳕鱼酶解液苦味肽的纯化鉴定[J].现代食品科技,2016,32(02):1-8.
[49]刘琳.功能性食品中多肽的分离分析方法研究[D].泰安:山东农业大学,2013.