English
新闻公告
More
化学进展 2008, Vol. 20 Issue (06): 975-983 前一篇   后一篇

• 综述与评论 •

蛋白质中二硫键的定位及其质谱分析*

仇晓燕1,2  崔勐1 刘志强1 刘淑莹1**   

  1. (1. 中国科学院长春应用化学研究所 长春质谱中心 长春 130022;
    2. 中国科学院研究生院 北京 100039)
  • 收稿日期:2007-07-31 修回日期:2007-09-17 出版日期:2008-06-24 发布日期:2008-06-24
  • 通讯作者: 刘淑莹

Protein Disulfide Bond Determination and Its Analysis by Mass Spectrometry

Qiu Xiaoyan1,2  Cui Meng1 Liu Zhiqiang1 Liu Shuying1**   

  1. (1. Changchun Center of Mass spectrometry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China; 2. Graduate School of the Chinese Academy of Sciences, Beijing 100039, China)
  • Received:2007-07-31 Revised:2007-09-17 Online:2008-06-24 Published:2008-06-24
  • Contact: Shuying Liu
二硫键是一种常见的蛋白质翻译后修饰,对稳定蛋白质的空间结构,保持及调节其生物活性等都有着非常重要的作用。因此,确定二硫键在蛋白质中的位置是全面了解含二硫键蛋白化学结构的重要方面。在众多实验方法中,现代质谱技术因其操作简单、快速、灵敏等优点而成为分析二硫键的重要手段。本文介绍了目前主要的定位二硫键的方法,以及质谱在二硫键定位分析中的应用与进展。

Disulfide bonds are one of the most common covalent posttranslational modifications of proteins. They play an important role in maintaining the three-dimensional structures of proteins, and their biological activities. Therefore, the determination of disulfide bonds becomes an important aspect of obtaining a comprehensive understanding of the chemical structure of a protein. Numerous experimental methods have been developed for the determination of disulfide bonds in proteins. Modern mass spectrometry has developed as an important tool for the analysis of disulfide bond patterns due to its advantages of being simple, rapid and sensitive. Some useful methods for assignment of disulfide bonds in proteins are introduced, the developments and applications of mass spectrometry in this area are reviewed.

中图分类号: 

()

[ 1 ] Thornton J M. J . Mol . Biol . , 1981 , 151 : 261 —287
[ 2 ] Creighton T E. Bioessays , 1988 , 8 : 57 —63
[ 3 ] Pace C N , Grimsley G R , Thomson J A , Barnett B J . J . Biol .Chem. , 1988 , 263 : 11820 —11825
[ 4 ] Matsumura M, Signor G, Matthews B W. Nature , 1989 , 342 :291 —293
[ 5 ] Wedemeyer W J , Welker E , Narayan M, Scheraga H A.Biochemistry , 2000 , 39 : 4207 —4216
[ 6 ] Pitt J J , da Silva E , Gorman J J . J . Biol . Chem. , 2000 , 275 :6469 —6478
[ 7 ] Harrison P M, Sternberg M J E. J . Mol . Biol . , 1994 , 244 :448 —463
[ 8 ] Abkevich V I , Shakhnovich E I. J . Mol . Biol . , 2000 , 300 :975 —985
[ 9 ] Mitchison C , Wells J A. Biochemistry , 1989 , 28 : 4807 —4815
[10] Jeffrey W N , Thomas E C. Biochemistry , 1994 , 33 : 5974 —5983
[11] Chuang C C , Chen C Y, Yang J M, et al . Proteins , 2003 , 53 :1 —5
[12] Scoble H A , Martin S A. Methods Enzymol . , 1990 , 193 : 519 —536
[13] Haniu M, Acklin C , Kenney W C , Rohde M F. Int . J . Pept .Protein Res. , 1994 , 43 : 81 —86
[14] Baneyx F , Mujacic M. Nat . Biotechnol . , 2004 , 22 : 1399 —1408
[15] Jones T A , Kjeldgaard M. Methods Enzymol . , 1997 , 277 : 173 —208
[16] Klaus W, Broger C , Gerber P , Senn H. J . Mol . Biol . , 1993 ,232 : 897 —906
[17] Ryle A P , Sanger F. Biochem. J . , 1955 , 60 : 535 —540
[18] Ryle A P , Sanger F , Smith L F , Kitai R. Biochem. J . , 1955 ,60 : 541 —556
[19] Spackman D H , Stein W H , Moore S. J . Biol . Chem. , 1960 ,235 : 648 —659
[20] Sanger F. Nature , 1953 , 171 : 1025 —1026
[21] Sanger F. Science , 1959 , 129 : 1340 —1344
[22] Brown J R , Hartley B S. Biochem. J . , 1966 , 101 : 214 —228
[23] Hirs C H W. Methods Enzymol . , 1967 , 11 : 475 —478
[24] Morris H R , Pucci P. Biochem. Biophys. Res. Commun. ,1985 , 126 : 1122 —1128
[25] Yazdanparast R , Andrews P C , Smith D L , Dixon J E. J . Biol .Chem. , 1987 , 262 : 2507 —2513
[26] Smith D L , Zhou Z. Methods Enzymol . , 1990 , 193 : 374 —389
[27] Zhou Z , Smith D L. J . Protein Chem. , 1990 , 9 : 523 —532
[28] Zhou Z , Smith D L. Biomed. Environ. Mass Spectrom. , 1990 ,19 : 782 —786
[29] Bauer M, Sun Y, Degenhardt C , Kozikowski B. J . Protein Chem. , 1993 , 12 : 759 —764
[30] Bordini E , Hamdan M, Righetti P G. Rapid Commun. Mass Spectrom. , 1999 , 13 : 1818 —1827
[31] Hoeprich P D , Doolittle R F. Biochemistry , 1983 , 22 : 2049 —2055
[32] Nishiuchi Y, Kumagaye K, Noda Y, Biopolymers , 1986 , 25(suppl . ) : S61 —S68
[33] Nishiuchi Y, Sakakibara S. FEBS Lett . , 1982 , 148 : 260 —262
[34] Shimonishi Y, Hidaka Y, Koizumi M. FEBS Lett . , 1987 , 215 :165 —170
[35] Cosena L , Sweeney E , Murphy J R. J . Biol . Chem. , 1997 , 272(52) : 32995 —33000
[36] Jones M D , Patterson S D , Lu H S. Anal . Chem. , 1998 , 70 :136 —143
[37] Yen T Y, Joshi R K, Yan H , et al . J . Mass Spectrom. , 2000 ,35 : 990 —1002
[38] Iahimizu T , Norioka S , Kanai M, Clarke A E , Sakiyama F. Eur.J . Biochem. , 1996 , 242 : 627 —635
[39] Glocker M O , Arbogast B , Deinzer M L. J . Am. Soc. Mass Spectrom. , 1995 , 6 : 638 —643
[40] Cole A R , Hall N E , Treutlein H R , Eddes J S , Reid G E ,Moritz R L , Simpson R J . J . Biol . Chem. , 1999 , 274 : 7207 —7215
[41] Holmes E H , Yen T Y, Thomas S , Joshi R , Nguyen A , Long T ,Gallet F , Maftah A , Julien R , Macher B A. J . Biol . Chem. ,2000 , 275 : 24237 —24245
[42] Hart P J , Deep S , Taylor A B , et al . Nat . Struct . Biol . , 2002 ,9 : 203 —208
[43] Fadel V , Bettendorff P , Herrmann T , et al . Toxicon , 2005 , 46 :759 —767
[44] Carr C , Aykent S , Kimack N M, Levine A D. Biochemistry ,1991 , 30 : 1515 —1523
[45] Kallestad J C , Shoyab M, Linsley P S. J . Biol . Chem. , 1991 ,266 : 8940 —8945
[46] Stewart A E , Raffioni S , Chaudhary T , Chait B T , Luporini P ,Bradshaw R A. Protein Sci . , 1992 , 1 : 777 —785
[47] Akashi S , Hirayama K, Seino T , et al . Biomed. Environ. Mass Spectrom. , 1988 , 15 : 541 —546
[48] Crimmins D L. Pept . Res. , 1989 , 2 : 395 —401
[49] Andrews P C , Villafranca J L. Current Research in Protein Chemistry. San Diego , CA: Academic Press , 1990. 95 —102
[50] Sandy J D , Flannery C R , Boynton R E , Neame P J . J . Biol .Chem. , 1990 , 265 : 21108 —21113
[51] Crimmins D L , Saylor M, Rush J , Thoma R S. Anal . Biochem. ,1995 , 226 : 355 —361
[52] Gray W R. Protein Sci . , 1993 , 2 : 1732 —1748
[53] Wu J , Gage D A , Watson J T. Anal . Biochem. , 1996 , 235 :161 —174
[54] Wu J , Watson J T. Protein Sci . , 1997 , 6 : 391 —398
[55] Fischer W H , Rivier J E , Craig A G. Rapid Commun. Mass Spectrom. , 1993 , 7 : 225 —228
[56] Gray W R. Protein Sci . , 1993 , 2 : 1749 —1755
[57] Li F , Liang S P. Peptides , 1999 , 20 : 1027 —1034
[58] 赵听友(Zhao T Y) , 曹瑛(Cao Y) , 范崇旭(Fan C X) . 化学学报(Acta Chimica Sinica) , 2005 , 63(2) : 163 —168
[59] Gray W R , Creighton T E. Protein Structure : A Practical Approach. Oxford : IRL Press , 1997. 165 —186
[60] Wu J , Watson J T. Anal . Biochem. , 1998 , 258 : 268 —276
[61] Van den Hooven H W, van den Burg H A , Vossen P , et al .Biochemistry , 2001 , 40 : 3458 —3466
[62] Katsumi A , Tuley E A , Bodo I. J . Biol . Chem. , 2000 , 275 :25585 —25594
[63] Bures E J , Hui J O , Young Y, et al . Biochemistry , 1998 , 37 :12172 —12177
[64] Schutte C G, Lemm T , Glombitza G J , Sandhoff K. Protein Sci . ,1998 , 7 : 1039 —1045
[65] Li J , Yen T Y, Allende ML Jr. J . Biol . Chem. , 2000 , 275 :41476 —41486
[66] Wu J , Watson J T. Methods Mol . Biol . , 2002 , 194 : 1 —22
[67] Qi J , Wu J , Watson J T , et al . Biochemistry , 2001 , 40 : 4531 —4538
[68] Andrews P C , Dixon J E. Anal . Biochem. , 1987 , 161 : 524 —528
[69] Burns J A , Butler J C , Moran J , Whitesides G M. J . Org.Chem. , 1991 , 56 : 2648 —2650
[70] Han J C , Han G Y. Anal . Biochem. , 1994 , 220 : 5 —10
[71] Getz E B , Xiao M, Chakrabarty T , Cooke R , Selvin P R. Anal .Biochem. , 1999 , 273 : 73 —80
[72] Gorman J J , Ferguson B L , Nguyen T N. Rapid Commun. Mass Spectrom. , 1996 , 10 : 529 —536
[73] Thomson J J . Rays of Positive Electricity and Their Application to Chemical Analysis. London : Longmans Green , 1913
[74] Barber M, Bordoli R S , Sedgwick R D , Tyler A N. J . Chem.Soc. Chem. Commun. , 1981 , 325 —327
[75] Torgerson D F , Skowronski R P , Macfarlane R D. Biochem.Biophys. Res. Commun. , 1974 , 60 : 616 —621
[76] H? kansson P , Kamensky I , Sundqvist B , Fohlman J , Petersen P ,McNeal C J , Macfarlane R D. J . Am. Chem. Soc. , 1982 , 104 :2948 —2949
[77] Sundqvist B , Roepstorff P , Fohlman J , et al . Science , 1984 ,696 —698
[78] Chait B T , Field F H. J . Am. Chem. Soc. , 1985 , 107 : 6743 —6744
[79] Chait B T , Field F H. Biochem. Biophys. Res. Commun. ,1986 , 134 : 420 —426
[80] Takao T , Yoshida M, Hong Y M, Aimoto S , Shimonishi Y.Biomed. Mass Spectrom. , 1984 , 11 : 549 —556
[81] Yazdanparast R , Andrews P , Smith D L , Dixon J E. Anal .Biochem. , 1986 , 153 : 348 —353
[82] Fenn J B , Mann M, Meng C K, Wong S F , Whitehouse C M.Science , 1989 , 246 : 64 —71
[83] Fenn J B , Mann M, Meng C K, Wong S F , Whitehouse C M.Mass Spectrom. Rev. , 1990 , 9 : 37 —41
[84] Karas M, Bachmann D , Bahr U , Hillenkamp F. Int . J . Mass Spectrom. Ion. Process. , 1987 , 78 : 53 —68
[85] Karas M, Hillenkamp F. Anal . Chem. , 1988 , 60 : 2299 —2301
[86] Hillenkamp F , Karas M, Beavis R C. Anal . Chem. , 1991 , 63 :1193A —1203A
[87] Tanaka K, Waki H , Ido Y, Akita S , Yoshida Y, Yoshida T.Rapid Commun. Mass Spectrom. , 1988 , 2 : 151 —153
[88] Vestal M L , Juhasz P , Martin S A. Rapid Commun. Mass Spectrom. , 1995 , 9 : 1044 —1050
[89] Burlingame A L , Boyd R K, Gaskell S J . Anal . Chem. , 1998 ,70 : 647R —716R
[90] Tetsuya S , Kazuo M, Toshikatsu O. FEBS Journal , 2000 , 267 :2380 —2389
[91] Bean M F , Carr S A. Anal . Biochem. , 1992 , 201 : 216 —226
[92] Gorman J J , Ferguson B L , Speelman D , Mills J . Protein Sci . ,1997 , 6 : 1308 —1315
[93] Mhatre R , Woodard J , Zeng C. Rapid Commun. Mass Spectrom. , 1999 , 13 : 2503 —2510
[94] Zhang W, Marzilli L A , Jason C , et al . Analytical Biochemistry ,2002 , 311 : 1 —9
[95] Yen T Y, Macher B A. Method Enzymol . , 2006 , 415 : 103 —113
[96] Yen T Y, Yan H , Macher B A. J . Mass Spectrom. , 2002 , 37 :15 —30
[97] Schnolzer M, Jedrzejewski P , Lehmann W D. Electrophoresis ,1996 , 17 : 945 —953
[98] Rao K C S , Carruth R T , Miyagi M. J . Proteome Res. , 2005 ,4 : 507 —514
[99] Rao K C S , Palamalai V , Miyagi M. Molecular & Cellular Proteomics , 2005 , 4 : 1550 —1557
[100] Wallis T P , Pitt J J , Gorman J J . Protein Sci . , 2001 , 10 :2251 —2271
[101] Traub W, Piez KA. Adv. Protein Chem. , 1971 , 25 : 243 —352
[102] Folk J E , Finlayson J S. Adv. Protein Chem. , 1977 , 31 : 1 —133
[103] Wold F. Methods Enzymol . , 1972 , 25 : 623 —651
[104] Peters K, Richards F M. Annu. Rev. Biochem. , 1977 , 46 :523 —551
[105] Zubarev R A , Kruger N A , Fridriksson E K. J . Am. Chem.Soc. , 1999 , 121 : 2857 —2862
[106] Ge Y, Lawhorn B G, ElNaggar M, et al . J . Am. Chem. Soc. ,2002 , 124 : 672 —678
[107] Kelleher N L , Lin H Y, Valaskovic GA , et al . J . Am. Chem.Soc. , 1999 , 121 : 806 —812
[108] McLafferty F W, Fridriksson E K, Horn D M. Science , 1999 ,284 : 1289 —1290
[109] Kelleher N L. Chem. Biol . , 2000 , 7 : R37 —R45
[110] Meng F , Cargile B J , Miller L M. Nat . Biotechnol . , 19 : 952 —957
[111] Patterson S D , Katta V. Anal . Chem. , 1994 , 66 : 3727 —3732
[112] Fukuyama Y, Iwamoto S , Tanaka K. J . Mass Spectrom. , 2006 ,41 : 191 —201
[113] Qiu X Y, Cui M, Liu S Y, et al . Rapid Commun. Mass Spectrom. , 2007 , 21(21) : 3520 —3525
[114] Qi J , Wu W, Watson J T , et al . J . Am. Soc. Mass Spectrom. ,2003 , 14 : 1032 —1038
[115] Fagerquist C K. Rapid Commun. Mass Spectrom. , 2004 , 18 :685 —700
[116] Happersberger H P , Bantscheff M, Barbirz S , Glocker M O.Methods Mol . Biol . , 2000 , 146 : 167 —184
[117] Qin J , Chait B T. Anal . Chem. , 1997 , 69 : 4002 —4009
[118] FenyêD. Comput . Appl . Biosci . , 1997 , 13 : 617 —618
[119] Thevis M, Loo R R O , Loo J A. J . Am. Soc. Mass Spectrom. ,2003 , 14 : 635 —647
[120] Clauser K R , Baker P R , Burlingame A L. Anal . Chem. , 1999 ,71 : 2871 —2882
[121] Aebersold R , Goodlett D R. Chem. Rev. , 2001 , 101 : 269 —295
[122] Chalkley R J , Baker P R , Hansen K C. Molecular and Cellular Proteomics , 2005 , 4 : 1189 —1193
[123] Chalkley R J , Baker P R , Huang L. Molecular and Cellular Proteomics , 2005 , 4 : 1194 —1204
[124] Schnaible V , Wefing S , Resemann A , et al . Anal . Chem. , 2002 , 74 : 4980 —4988
[125] Schnaible V , Wefing S , Bücker A , et al . Anal . Chem. , 2002 ,74 : 2386 —2393
[126] Wefing S , Schnaible V , Hoffmann D. Anal . Chem. , 2006 , 78 :1235 —1241
[127] De Koning L J , Kasper P T , de Jong L , et al . FEBS J . , 2006 ,273 : 281 —291
[128] Klose J , Wendt N , Rothemund S , et al . Protein Sci . , 2004 , 13 :2470 —2475
[129] Lowe E K, Anema S G, Bienvenue A , et al . J . Agric. Food Chem. , 2004 , 52 : 7669 —7680
[130] Schilling B , Row R H , Gibson B W, et al . J . Am. Soc. Mass Spectrom. , 2003 , 14 : 834 —850
[131] Back J W, Notenboom V , de Koning L J , et al . Anal . Chem. ,2002 , 74 : 4417 —4422
[132] Zhang D Y, Liang S P. J . Protein Chem. , 1993 , 12 : 735 —740
[133] Peng K, Shu Q , Liang S P , et al . J . Biol . Chem. , 2002 , 277 :47564 —47571
[134] Li F , Liang S P. Peptides , 1999 , 20 : 1027 —1034
[135] Shu Q , Huang R H , Liang S P. Eur. J . Biochem. , 2001 , 268 :2301 —2307
[136] 刘中华(Liu Z H) , 梁宋平(Liang S P) . 高等学校化学学报(Chemical Journal of Chinese Universities ) , 2003 , 24 ( 10 ) :1815 —1819
[137] 张鹏飞(Zhang P F) , 肖顺勇(Xiao S Y) , 梁宋平(Liang S P) .生物化学与生物物理进展( Prog. Biochem. Biophys. ) ,2004 , 31 (6) : 550 —555
[138] Gorman J J , Wallis T P , Pitt J J . J . Mass Spectrom. Rev. ,2002 , 21 : 183 —216
[139] Poerio E , Caporale C , Carrano L , Pucci P , Buonocore V. Eur.J . Biochem. , 1991 , 99 : 595 —600
[140] Robertson J G, Adams G W, Medzihradszky K F , et al .Biochem. , 1994 , 33 : 11563 —11575
[141] Vaccaro A M, Salvioli R , Barca A , et al . J . Biol . Chem. ,1995 , 270 : 9953 —9960
[142] Gehrig P M, Biemann K. Pept . Res. , 1996 , 9 : 308 —314
[143] Hodder A N , Crewther P E , Matthew M L , et al . J . Biol .Chem. , 1996 , 271 : 29446 —29452
[144] Calvete J J , Schrader M, Raida M, et al . FEBS Lett . , 1997 ,416 : 197 —202
[145] Sparrow L G, McKern N M, Gorman J J , et al . J . Biol . Chem. ,1997 , 272 : 29460 —29467
[146] Haniu M, Arakawa T , Bures EJ , et al . J . Biol . Chem. , 1998 ,273 : 28691 —28699
[147] Cole A R , Hall N E , Treutlein H R , et al . J . Biol . Chem. ,1999 , 274 : 7207 —7215
[148] Moritz R L , Hall N E , Connolly L M, Simpson R J . J . Biol .Chem. , 2001 , 276 : 8244 —8253
[149] Chong J M, Bren A , Speicher D W. J . Biol . Chem. , 2002 ,277 : 5134 —5144
[150] Lansmann S , Schuette C G, Sandhoff K, et al . Eur. J .Biochem. , 2003 , 270 : 1076 —1088
[151] Tie J K, Mutucumarana V P , Stafford D W, et al . J . Biol .Chem. , 2003 , 278 : 45468 —45475
[152] Barrientos L G, Martin A M, Sanchez A , et al . Biochem.Biophys. Res. Commun. , 2004 , 323 : 696 —702
[153] Wallis T P , Huang C Y, Gorman J J , et al . J . Biol . Chem. ,2004 , 279 : 20729 —20741
[154] Wagner L A , Ohnuki L E , Parsawar K, et al . Protein Journal ,2007 ,26 : 13 —18

[1] 赵超, 蔡宗苇. 基于质谱成像和组学分析的环境毒理研究[J]. 化学进展, 2021, 33(4): 503-511.
[2] 王子璇, 厉欣, 再帕尔·阿不力孜. 化学衍生用于代谢物异构体质谱分析[J]. 化学进展, 2021, 33(3): 406-416.
[3] 杨笑宇, 贾珊珊, 张娟, 亓英华, 胡雪雯, 沈宝洁, 钟鸿英. 质谱光电离/解离技术和生物分子结构鉴定[J]. 化学进展, 2021, 33(12): 2316-2333.
[4] 蔡乐斯, 夏梦婵, 李展平, 张四纯, 张新荣. 二次离子质谱生物成像[J]. 化学进展, 2021, 33(1): 97-110.
[5] 李瑜玲, 赵君博, 郭寅龙. 常压电喷雾离子化的机理及应用[J]. 化学进展, 2019, 31(1): 94-109.
[6] 任娟, 边申, 王奕允, 孔祥蕾. 幻数团簇丝氨酸八聚体:结构和手性特征[J]. 化学进展, 2018, 30(4): 383-397.
[7] 顾芳婷, 胡敏*, 郑竞, 郭松. 大气颗粒物中有机硝酸酯的研究进展[J]. 化学进展, 2017, 29(9): 962-969.
[8] 刘婧靖, 何晓伟, 何燕, 喻目千, 蒋乐, 陈波. 纸喷雾敞开式质谱法的发展和应用[J]. 化学进展, 2017, 29(6): 659-666.
[9] 王方丽, 洪敏, 许丽丹, 耿志荣. 基于纳米材料的表面辅助激光解吸离子化质谱研究[J]. 化学进展, 2015, 27(5): 571-584.
[10] 田志美, 刘汪丹, 程龙玖. 硫醇保护金团簇的实验和理论研究现状[J]. 化学进展, 2015, 27(12): 1743-1753.
[11] 徐冲, 范艳璇, 范琳媛, 曹洁*, 胡长文*. 质谱在多金属氧簇化学中的应用[J]. 化学进展, 2013, 25(05): 809-820.
[12] 储根柏, 陈军, 刘付轶*, 盛六四* . 气相自由基反应动力学的光电离质谱研究[J]. 化学进展, 2012, 24(11): 2097-2105.
[13] 彭晓敏, 张金超, 高愈希, 柴之芳. 金属蛋白的提取分离技术[J]. 化学进展, 2012, 24(05): 834-843.
[14] 张佳玲, 霍飞凤, 周志贵, 白玉, 刘虎威. 实时直接分析质谱的原理及应用[J]. 化学进展, 2012, 24(01): 101-109.
[15] 石磊, 刘淑莹, Zubarev Roman. 电子捕获解离技术在生物质谱中的作用[J]. 化学进展, 2011, 23(8): 1710-1718.