生物模拟转氨反应在蛋白质修饰中的应用
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  • 英文篇名:Applications of Biomimetic Transamination Reaction to Protein Modifications
  • 作者:王志鹏 ; 李娟 ; 李宜明
  • 英文作者:Wang Zhipeng;Li Juan;Li Yiming;Department of Chemistry, Tsinghua University;School of Medical Engineering, Hefei University of Technology;
  • 关键词:生物模拟转氨反应 ; 磷酸吡哆醛 ; 生物正交反应 ; 蛋白质N末端修饰
  • 英文关键词:biomimetic transamination reaction;;pyridoxal phosphate;;bio-orthogonal reaction;;protein N-terminal modification
  • 中文刊名:YJHU
  • 英文刊名:Chinese Journal of Organic Chemistry
  • 机构:清华大学化学系;合肥工业大学医学工程学院;
  • 出版日期:2013-09-15
  • 出版单位:有机化学
  • 年:2013
  • 期:v.33;No.298
  • 基金:国家自然科学基金(Nos.21102083,21002056)资助项目~~
  • 语种:中文;
  • 页:YJHU201309002
  • 页数:10
  • CN:09
  • ISSN:31-1321/O6
  • 分类号:35-44
摘要
作为化学生物学研究的重要方向,生物正交反应的发展与应用为生命科学研究提供了有力武器.利用生物正交反应,人们可以将合成分子与目标天然大分子在特定位点上实现特异性连接,进而达成诸如标记、定位、功能化、固定等一系列目标.生物模拟转氨反应及其衍生反应是一类特异性蛋白质N端修饰的生物正交反应,与天然蛋白侧链、C端的连接反应相互补充.由于该反应具有高效性、通用性、温和性及不需要引入突变或非天然氨基酸等优点,从发现以来已较为广泛地运用于蛋白质化学生物学的多个相关领域.在介绍其基本原理及反应优化的基础上,综述该类反应的发展及应用情况.
        Bio-orthogonal reactions provide powerful tools for the life science research, and their discovery as well as development is important in chemical biology. Synthetic molecules can be covalently ligated to natural biomacromolecules at specific sites with high selectivity to achieve diverse goals such as labeling, localization, functionalization and immobilization.Biomimetic transamination reaction is a special protein N-terminal modification orthogonal reaction, which can serve as a supplement to the ligation methods at amino acid residue side chains or protein C-terminus. With several advantages including high efficiency, adaptable applicability, mild operation conditions, and no need for mutation, biomimetic transamination reaction has been broadly utilized in several related realms of protein chemical biology. This review summarizes the development and application of biomimetic transamination reaction for protein modifications.
引文
[1]Sletten,E.M.;Bertozzi,C.R.Angew.Chem.,Int.Ed.2009,48,6974.
    [2](a)Lim,R.K.;Lin,Q.Sci.China Chem.2010,53,61.(b)Liu,Q.;Zhang,Q.;Chen,S.;Zhou,J.;Lei,X.Chin.J.Org.Chem.2012,32,1846(in Chinese).(刘清,张秋禹,陈少杰,周健,雷星锋,有机化学,2012,32,1846.)
    [3]Joo,C.;Balci,H.;Ishitsuka,Y.;Buranachai,C.;Ha,T.Annu.Rev.Biochem.2008,77,51.
    [4]Vriezema,D.M.;Aragonès,M.C.;Elemans,J.A.A.W.;Cornelissen,J.J.L.M.;Rowan,A.E.;Nolte,R.J.M.Chem.Rev.2005,105,1445.
    [5]Pasut,G.;Veronese,F.M.Prog.Polym.Sci.2007,32,933.
    [6](a)Jiang,Z.-Y.;Gao,R.;Xu,S.-W.;Wang,Y.-Q.;Gao,Y.Chin.J.Biochem.Pharm.2002,23,102(in Chinese).(姜忠义,高蓉,许松伟,王艳强,高岩,中国生化药物杂志,2002,23,102.)(b)Qie,J.;Ma,J.;Wang,L.;Xu,X.;Zhou,W.;Qi,C.;Zhao,X.;Zhang,Y.;Liu,K.Chin.J.Chem.2009,27,805.(c)Lu,J.;Liu,Q.;Luo,G.;Wang,Y.Chin.J.Org.Chem.2009,29,1167(in Chinese).(路娟,刘清飞,罗国安,王义明,有机化学,2009,29,1167.)
    [7]Tsien,R.Y.Annu.Rev.Biochem.1998,67,509.
    [8]Yao,J.Z.;Uttamapinant,C.;Poloukhtine,A.;Baskin,J.M.;Codelli,J.A.;Sletten,E.M.;Bertozzi,C.R.;Popik,V.V.;Ting,A.Y.J.Am.Chem.Soc.2012,134,3720.
    [9]Ling,J.J.;Policarpo,R.L.;Rabideau,A.E.;Liao,X.;Pentelute,B.L.J.Am.Chem.Soc.2012,134,10749.
    [10]Noren,C.J.;Anthonycahill,S.J.;Grifth,M.C.;Schultz,P.G.Science 1989,244,182.
    [11]Hao,Z.;Hong,S.;Chen,X.;Chen,P.R.Acc.Chem.Res.2011,44,742.
    [12]Li,Y.M.;Yang,M.Y.;Huang,Y.C.;Song,X.D.;Liu,L.;Chen,P.R.Chem.Sci.2012,3,2766.
    [13]Wang,Y.;Ye,X.-S.Acta Chim.Sinica 2012,70,2208(in Chinese).(王玥,叶新山,化学学报,2012,70,2208.)
    [14]Li,J.;Wang,J.;Chen,P.R.Acta Chim.Sinica 2012,70,1439(in Chinese).(李劼,王杰,陈鹏,化学学报,2012,70,1439.)
    [15]Gauthier,M.A.;Klok,H.Chem.Commun.2008,44,2591.
    [16]Kovacs,E.W.;Hooker,J.M.;Romanini,D.W.;Holder,P.G.;Berry,K.E.;Francis,M.B.Bioconjugate Chem.2007,18,1140 1147.
    [17]Li,Y.M.;Pan,M.;Li,Y.T.;Huang,Y.C.;Guo,Q.X.Org.Biomol.Chem.2013,11,2624.
    [18]Bernardes,G.J.L.;Grayson,E.J.;Thompson,S.;Chalker,J.M.;Errey,J.C.;F.El Oualid,Timothy D.W.C.;Benjamin,G.D.Angew.Chem.,Int.Ed.2008,47,2244.
    [19]Kent,S.B.H.Chem.Soc.Rev.2009,38,338.
    [20]Tong,G.J.;Hsiao,S.C.;Carrico,Z.M.;Francis,M.B.J.Am.Chem.Soc.2009,131,11174.
    [21]Esser-Kahn,A.P.;Iavarone,A.T.;Francis,M.B.J.Am.Chem.Soc.2008,130,15820.
    [22]Stephanopoulos,N.;Francis,M.B.Nat.Chem.Biol.2011,7,876.
    [23](a)Dawson,P.E.;Muir,T.W.;Clark-Lewis,I.;Kent,S.B.H.Science 1994,266,776.(b)Dai,X.;Fan,C.;Cao,Y.;Liu,S.;Jiang,H.;Chen,J.Acta Chim.Sinica 2010,68,667(in Chinese).(代先东,范崇旭,曹瑛,刘尚义,蒋辉,陈冀胜,化学学报,2010,68,667.)(c)Zheng,J.S.;Chang,H.N.;Wang,F.L.;Liu,L.J.Am.Chem.Soc.2011,133,11080.
    [24]Fang,G.M.;Li,Y.M.;Shen,F.;Huang,Y.C.;Li,J.B.;Lin,Y.;Cui,H.K.;Liu,L.Angew.Chem.,Int.Ed.2011,50,7645.
    [25](a)Li,Y.M.;Yang,M.Y.;Huang,Y.C.;Li,Y.T.;Chen,P.R.;Liu,L.ACS Chem.Biol.2012,7,1015.(b)Fang,G.M.;Wang,J.X.;Liu,L.Angew.Chem.,Int.Ed.2012,51,10347.(c)Zheng,J.S.;Tang,S.;Guo,Y.;Chang,H.N.;Liu,L.ChemBioChem 2012,13,542.
    [26](a)Li,X.;Zhang,L.;Hall,S.E.;Tam,J.P.Tetrahedron Lett.2000,41,4069.(b)Li,X.;Zhang,L.;Zhang,W.;Hall,S.E.;Tam,J.P.Org.Lett.2000,2,3075.
    [27]Dirksen,A.;Dirksen,S.;Hackeng,T.M.;Dawson,P.E.J.Am.Chem.Soc.2006,128,15602.
    [28]Dirksen,A.;Dawson,P.E.Bioconjugate Chem.2008,19,2543.
    [29]Dirksen,A.;Hackeng,T.M.;Dawson,P.E.Angew.Chem.,Int.Ed.2006,45,7581.
    [30]Geoghegan,K.F.;Stroh,J.G.Bioconjugate Chem.1992,3,138.
    [31](a)Liu,L.;Breslow,R.J.Am.Chem.Soc.2002,124,4978.(b)Liu,L.;Rozenman,M.;Breslow,R.J.Am.Chem.Soc.2002,124,12660.
    [32]Toney,M.D.Arch.Biochem.Biophys.2005,433,279.
    [33]Cook,P.D.;Thoden,J.B.;Holden,H.M.Protein Sci.2006,15,2093.
    [34]Gilmore,J.M.;Scheck,R.A.;Esser-Kahn,A.P.;Joshi,N.S.;Francis,M.B.Angew.Chem.,Int.Ed.2006,45,5307.
    [35]Dixon,H.B.F.J.Protein Chem.1984,3,99.
    [36](a)Vázquez,M.A.;Mu oz,F.;Donoso,J.;García Blanco,F.Amino Acids 1992,3,81.(b)Liu,L.;Zhou,W.;Chruma,J.;Breslow,R.J.Am.Chem.Soc.2004,126,8136.
    [37]Scheck,R.A.;Dedeo,M.T.;Iavarone,A.T.;Francis,M.B.J.Am.Chem.Soc.2008,130,11762.
    [38]Witus,L.S.;Moore,T.;Thuronyi,B.W.;Esser-Kahn,A.P.;Scheck,R.A.;Iavarone,A.T.;Francis,M.B.J.Am.Chem.Soc.2010,132,16812.
    [39]Zhang,M.;Li,J.;Guo,Q.Chin.J.Chem.2011,29,1715.
    [40]Liu,L.;Breslow,R.J.Am.Chem.Soc.2003,125,12110.
    [41]Lee,S.H.;Goto,T.;Oe,T.Chem.Res.Toxicol.2008,21,2237.
    [42]Kalia,J.;Raines,R.T.Angew.Chem.,Int.Ed.2008,47,7523.
    [43]Ning,X.;Temming,R.P.;Dommerholt,J.;Guo,J.;Ania,D.B.;Debets,M.F.;Wolfert,M.A.;Boons,G.;van Delft,F.L.Angew.Chem.,Int.Ed.2010,122,3129.
    [44]Debets,M.F.;van Berkel,S.S.;Dommerholt,J.;Dirks,A.J.;Rutjes,F.P.J.T.;van Delft,F.L.Acc.Chem.Res.2011,44,805.
    [45]Alam,J.;Keller,T.H.;Loh,T.-P.J.Am.Chem.Soc.2010,132,9546.
    [46]Mukaiyama,T.;Narasaka,K.;Banno,K.Chem.Lett.1973,2,1011.
    [47]Sasaki,T.;Kodama,K.;Suzuki,H.;Fukuzawa,S.;Tachibana,K.Bioorg.Med.Chem.Lett.2008,18,4550.
    [48]Antos,J.M.;Francis,M.B.Curr.Opin.Chem.Biol.2006,10,253.
    [49]Alam,J.;Keller,T.H.;Loh,T.-P.Chem.Commun.2011,47,9066.
    [50]Kung,K.K.Y.;Li,G.L.;Zou,L.;Chong,H.C.;Leung,Y.C.;Wong,K.H.;Lo,V.K.Y.;Che,C.M.;Wong,M.K.Org.Biomol.Chem.2012,10,925.
    [51]Crocheta,A.P.;Kabirc,M.M.;Francisa,M.B.;Paavola,C.D.Biosens.Bioelectron.2010,26,55.
    [52]Esser-Kahn,A.P.;Francis,M.B.Angew.Chem.,Int.Ed.2008,120,3811.
    [53]Gao,W.;Liu,W.;Mackaya,J.A.;Zalutskyd,M.R.;Toonec,E.J.;Chilkoti,A.Proc.Natl.Acad.Sci.U.S.A.2009,106,15231.
    [54]Lempens,E.H.M.;Merkx,M.;Tirrell,M.;Meijer,E.W.Bioconjugate Chem.2011,22,397
    [55]Carrico,Z.M.;Farkas,M.E.;Zhou,Y.;Hsiao,S.C.;Marks,J.D.;Chokhawala,H.;Clark,D.S.;Francis M.B.ACS Nano.2012,6,6675.
    [56]Scheck,R.A.;Francis,M.B.ACS Chem.Biol.2007,2,247.
    [57]Netirojjanakul,C.;Witus,L.S.;Behrens,C.R.;Weng,C.H.;Iavaroneab,A.T.;Francis,M.B.Chem.Sci.2013,4,266.
    [58]Min,D.;Mrksich,M.Curr.Opin.Chem.Biol.2004,8,554.
    [59]Rusmini,F.;Zhong,Z.;Jan,F.Biomacromolecules 2007,8,1775.
    [60]Jonkheijm,P.;Weinrich,D.;Schr der,H.;Niemeyer,C.M.;Waldmann,H.Angew.Chem.,Int.Ed.2008,47,9618.
    [61]Kausaite-Minkstimiene,A.;Ramanaviciene,A.;Kirlyte,J.;Ramanavicius,A.Anal.Chem.2010,82,6401.
    [62]Liu,L.;Hong,Z.Y.;Wong,C.H.ChemBioChem 2006,7,429.
    [63]Watzke,A.;K hn,M.;Gutierrez-Rodriguez,M.;Wacker,R.;Schr der,H.;Breinbauer,R.;Kuhlmann,J.;Alexandrov,K.;Niemeyer,C.M.;Goody,R.S.;Waldmann,H.Angew.Chem.,Int.Ed.2006,45,1408.
    [64]Park,S.;Yousaf,M.N.Langmuir 2008,24,6201.
    [65]Lempens,E.H.M.;Helms,B.A.;Merkx,M.;Meijer,E.W.ChemBioChem 2009,10,658.
    [66]Broyer,R.M.;Schopf,E.;Kolodziej,C.M.;Chen,Y.;Maynard,H.D.Soft Matter 2011,7,9972.
    [67]Christman,K.L.;Broyer,R.M.;Tolstyka,Z.P.;Maynard,H.D.J.Mater.Chem.2007,17,2021.
    [68]Christman,K.L.;Broyer,R.M.;Schopf,E.;Kolodziej,C.M.;Chen,Y.;Maynard,H.D.Langmuir 2011,27,1415.
    [69]Richa,R.L.;Myszka,D.G.J.Mol.Recognit.2010,23,1.
    [70]Dettin,M.;Muncan,N.;Bugatti,A.;Grezzo,F.;Danesin,R.;Rusnati,M.Bioconjugate Chem.2011,22,1753.
    [71]Wang,X.;Canary,J.W.Bioconjugate Chem.2012,23,2329.
    [72]Dedeo,M.T.;Duderstadt,K.E.;Berger,J.M.;Francis M.B.Nano Lett.2010,10,181.
    [73]Onodera,T.;Niikura,K.;Iwasaki,N.;Nagahori,N.;Shimaoka,H.;Kamitani,R.;Majima,T.;Minami,A.;Nishimura,S.Biomacromolecules 2006,7,2949.
    [74]Dendane,N.;Hoang,A.;Defrancq,E.;Vinet,F.;Dumy,P.Bioorg.Med.Chem.Lett.2008,18,2540.
    [75]Witus,L.S.;Francis M.B.Acc.Chem.Res.2011,44,774.
    [76]Krishna,O.D.;Kiick,K.L.Peptide Sci.2009,94,32.
    [77]Baslé,E.;Joubert,N.;Pucheault,M.Cell 2010,17,213.

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