메뉴 건너뛰기




Volumn 24, Issue 4, 2013, Pages 265-269

Review Design of thiol-containing amino acids for native chemical ligation at non-Cys sites

Author keywords

Desulfurization; Native chemical ligation; Protein chemical synthesis

Indexed keywords


EID: 84876563894     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2013.03.013     Document Type: Article
Times cited : (24)

References (46)
  • 1
    • 0027944205 scopus 로고
    • Synthesis of proteins by native chemical ligation
    • P.E. Dawson, T.W. Muir, L.C. Lewis, and S.B.H. Kent Synthesis of proteins by native chemical ligation Science 266 1994 776 779
    • (1994) Science , vol.266 , pp. 776-779
    • Dawson, P.E.1    Muir, T.W.2    Lewis, L.C.3    Kent, S.B.H.4
  • 2
    • 34247569910 scopus 로고    scopus 로고
    • Convergent chemical synthesis and high-resolution X-ray structure of human lysozyme
    • T. Durek, V.Y. Torbeev, and S.B.H. Kent Convergent chemical synthesis and high-resolution X-ray structure of human lysozyme Proc. Natl. Acad. Sci. U.S.A. 104 2007 4846 4851
    • (2007) Proc. Natl. Acad. Sci. U.S.A. , vol.104 , pp. 4846-4851
    • Durek, T.1    Torbeev, V.Y.2    Kent, S.B.H.3
  • 3
    • 34248230589 scopus 로고    scopus 로고
    • Convergent chemical synthesis and crystal structure of a 203 amino acid 'covalent dimer' HIV-1 protease enzyme molecule
    • V.Y. Torbeev, and S.B.H. Kent Convergent chemical synthesis and crystal structure of a 203 amino acid 'covalent dimer' HIV-1 protease enzyme molecule Angew. Chem. Int. Ed. 46 2007 1667 1670
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 1667-1670
    • Torbeev, V.Y.1    Kent, S.B.H.2
  • 4
    • 44849100496 scopus 로고    scopus 로고
    • Chemically ubiquitylated histone H2B stimulates hDot1L-mediated intranucleosomal methylation
    • R.K. McGinty, J. Kim, C. Chatterjee, R.G. Roeder, and T.W. Muir Chemically ubiquitylated histone H2B stimulates hDot1L-mediated intranucleosomal methylation Nature 453 2008 812 816
    • (2008) Nature , vol.453 , pp. 812-816
    • McGinty, R.K.1    Kim, J.2    Chatterjee, C.3    Roeder, R.G.4    Muir, T.W.5
  • 5
    • 84867057855 scopus 로고    scopus 로고
    • Convergent chemical synthesis of proteins by ligation of peptide hydrazides
    • G.M. Fang, J.X. Wang, and L. Liu Convergent chemical synthesis of proteins by ligation of peptide hydrazides Angew. Chem. Int. Ed. 51 2012 10347 10350
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 10347-10350
    • Fang, G.M.1    Wang, J.X.2    Liu, L.3
  • 6
    • 79961241515 scopus 로고    scopus 로고
    • Protein chemical synthesis by ligation of peptide hydrazides
    • G.M. Fang, Y.M. Li, and F. Shen Protein chemical synthesis by ligation of peptide hydrazides Angew. Chem. Int. Ed. 50 2011 7645 7649
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 7645-7649
    • Fang, G.M.1    Li, Y.M.2    Shen, F.3
  • 7
    • 79960594926 scopus 로고    scopus 로고
    • Fmoc synthesis of peptide thioesters without post-chain-assembly manipulation
    • J.S. Zheng, H.N. Chang, F.L. Wang, and L. Liu Fmoc synthesis of peptide thioesters without post-chain-assembly manipulation J. Am. Chem. Soc. 133 2011 11080 11083
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 11080-11083
    • Zheng, J.S.1    Chang, H.N.2    Wang, F.L.3    Liu, L.4
  • 9
    • 0033791223 scopus 로고    scopus 로고
    • Synthesis of native protein by chemical ligation
    • P.E. Dawson, and S.B.H. Kent Synthesis of native protein by chemical ligation Annu. Rev. Biochem. 69 2000 923 960
    • (2000) Annu. Rev. Biochem. , vol.69 , pp. 923-960
    • Dawson, P.E.1    Kent, S.B.H.2
  • 10
    • 0030037155 scopus 로고    scopus 로고
    • Extending the applicability of native chemical ligation
    • L.E. Canne, S.J. Bark, and S.B.H. Kent Extending the applicability of native chemical ligation J. Am. Chem. Soc. 118 1996 5891 5896
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 5891-5896
    • Canne, L.E.1    Bark, S.J.2    Kent, S.B.H.3
  • 11
    • 0036570182 scopus 로고    scopus 로고
    • Extending synthetic access to proteins with a removable acyl transfer auxiliary
    • J. Offer, C.N.C. Boddy, and P.E. Dawson Extending synthetic access to proteins with a removable acyl transfer auxiliary J. Am. Chem. Soc. 124 2002 4642 4646
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 4642-4646
    • Offer, J.1    Boddy, C.N.C.2    Dawson, P.E.3
  • 12
    • 0034808792 scopus 로고    scopus 로고
    • Selenocysteine in native chemical ligation and expressed protein ligation
    • R.J. Hondal, B.L. Nilsson, and R.T. Raines Selenocysteine in native chemical ligation and expressed protein ligation J. Am. Chem. Soc. 123 2001 5140 5141
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 5140-5141
    • Hondal, R.J.1    Nilsson, B.L.2    Raines, R.T.3
  • 13
    • 77956909658 scopus 로고    scopus 로고
    • Traceless ligation of cysteine peptides using selective deselenization
    • N. Metanis, E. Keinan, and P.E. Dawson Traceless ligation of cysteine peptides using selective deselenization Angew. Chem. Int. Ed. 49 2010 7049 7053
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 7049-7053
    • Metanis, N.1    Keinan, E.2    Dawson, P.E.3
  • 14
    • 51449087558 scopus 로고    scopus 로고
    • Chemoselective peptide cyclization by traceless staudinger ligation
    • R. Kleineweischede, and C.P.R. Hackenberger Chemoselective peptide cyclization by traceless staudinger ligation Angew. Chem. Int. Ed. 47 2008 5984 5988
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5984-5988
    • Kleineweischede, R.1    Hackenberger, C.P.R.2
  • 15
    • 33746190644 scopus 로고    scopus 로고
    • Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and α-ketoacids
    • J.W. Bode, R.M. Fox, and K.D. Baucom Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and α-ketoacids Angew. Chem. Int. Ed. 45 2006 1248 1252
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 1248-1252
    • Bode, J.W.1    Fox, R.M.2    Baucom, K.D.3
  • 16
    • 33644888786 scopus 로고    scopus 로고
    • Convergent glycopeptide synthesis by traceless staudinger ligation and enzymatic coupling
    • L. Liu, Z.Y. Hong, and C.H. Wong Convergent glycopeptide synthesis by traceless staudinger ligation and enzymatic coupling ChemBioChem 7 2006 429 432
    • (2006) ChemBioChem , vol.7 , pp. 429-432
    • Liu, L.1    Hong, Z.Y.2    Wong, C.H.3
  • 17
    • 0035977638 scopus 로고    scopus 로고
    • Synthesis of peptides and proteins without cysteine residues by native chemical ligation combined with desulfurization
    • L.Z. Yan, and P.E. Dawson Synthesis of peptides and proteins without cysteine residues by native chemical ligation combined with desulfurization J. Am. Chem. Soc. 123 2001 526 533
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 526-533
    • Yan, L.Z.1    Dawson, P.E.2
  • 18
    • 33847791752 scopus 로고    scopus 로고
    • Selective desulfurization of cysteine in the presence of Cys(Acm) in polypeptides obtained by native chemical ligation
    • B.L. Pentelute, and S.B.H. Kent Selective desulfurization of cysteine in the presence of Cys(Acm) in polypeptides obtained by native chemical ligation Org. Lett. 9 2007 687 690
    • (2007) Org. Lett. , vol.9 , pp. 687-690
    • Pentelute, B.L.1    Kent, S.B.H.2
  • 19
    • 21244494055 scopus 로고    scopus 로고
    • Total chemical synthesis and X-ray crystal structure of a protein diastereomer: [D-Gln35]Ubiquitin
    • D. Bang, G.I. Makhatadze, V. Tereshko, A.A. Kossiakoff, and S.B. Kent Total chemical synthesis and X-ray crystal structure of a protein diastereomer: [D-Gln35]Ubiquitin Angew. Chem. Int. Ed. 44 2005 3852 3856
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 3852-3856
    • Bang, D.1    Makhatadze, G.I.2    Tereshko, V.3    Kossiakoff, A.A.4    Kent, S.B.5
  • 20
    • 37349094422 scopus 로고    scopus 로고
    • Free-radical-based, specific desulfurization of cysteine: A powerful advance in the synthesis of polypeptides and glycopolypeptides
    • Q. Wan, and S.J. Danishefsky Free-radical-based, specific desulfurization of cysteine: a powerful advance in the synthesis of polypeptides and glycopolypeptides Angew. Chem. Int. Ed. 46 2007 9248 9252
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 9248-9252
    • Wan, Q.1    Danishefsky, S.J.2
  • 21
    • 79954987530 scopus 로고    scopus 로고
    • Chemical synthesis and expression of the HIV-1 Rev protein
    • P. Siman, O. Blatt, and T. Moyal Chemical synthesis and expression of the HIV-1 Rev protein ChemBioChem 12 2011 1097 1104
    • (2011) ChemBioChem , vol.12 , pp. 1097-1104
    • Siman, P.1    Blatt, O.2    Moyal, T.3
  • 22
  • 23
    • 84866427431 scopus 로고    scopus 로고
    • Engineering of therapeutic polypeptides through chemical synthesis: Early lessons from human parathyroid hormone and analogues
    • S.W. Dong, S.Y. Shang, and J.F. Li Engineering of therapeutic polypeptides through chemical synthesis: early lessons from human parathyroid hormone and analogues J. Am. Chem. Soc. 134 2012 15122 15129
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 15122-15129
    • Dong, S.W.1    Shang, S.Y.2    Li, J.F.3
  • 24
    • 79951662569 scopus 로고    scopus 로고
    • Hydrazine-sensitive thiol protecting group for peptide and protein chemistry
    • F. Shen, Z.P. Zhang, J.B. Li, Y. Lin, and L. Liu Hydrazine-sensitive thiol protecting group for peptide and protein chemistry Org. Lett. 13 2011 568 571
    • (2011) Org. Lett. , vol.13 , pp. 568-571
    • Shen, F.1    Zhang, Z.P.2    Li, J.B.3    Lin, Y.4    Liu, L.5
  • 25
    • 79251547705 scopus 로고    scopus 로고
    • Hexafluoro-2-propanol as a potent cosolvent for chemical ligation of membrane proteins
    • F. Shen, S. Tang, and L. Liu Hexafluoro-2-propanol as a potent cosolvent for chemical ligation of membrane proteins Sci. China Chem. 54 2011 110 116
    • (2011) Sci. China Chem. , vol.54 , pp. 110-116
    • Shen, F.1    Tang, S.2    Liu, L.3
  • 26
    • 84856330144 scopus 로고    scopus 로고
    • Chemical synthesis of a cyclotide via intramolecular cyclization of peptide O-esters
    • J.S. Zheng, H.N. Chang, J. Shi, and L. Liu Chemical synthesis of a cyclotide via intramolecular cyclization of peptide O-esters Sci. China Chem. 55 2012 64 69
    • (2012) Sci. China Chem. , vol.55 , pp. 64-69
    • Zheng, J.S.1    Chang, H.N.2    Shi, J.3    Liu, L.4
  • 27
    • 84876554020 scopus 로고    scopus 로고
    • Synthesis of cyclic tetrapeptides via ligation of peptide hydrazides
    • S. Tang, J. Zheng, K. Yang, and L. Liu Synthesis of cyclic tetrapeptides via ligation of peptide hydrazides Acta Chim. Sinica 70 2012 1471 1476
    • (2012) Acta Chim. Sinica , vol.70 , pp. 1471-1476
    • Tang, S.1    Zheng, J.2    Yang, K.3    Liu, L.4
  • 28
    • 84863229328 scopus 로고    scopus 로고
    • Synthesis of cyclic peptides and cyclic proteins via ligation of peptide hydrazides
    • J.S. Zheng, S. Tang, Y. Guo, H.N. Chang, and L. Liu Synthesis of cyclic peptides and cyclic proteins via ligation of peptide hydrazides Chembiochem 13 2012 542 546
    • (2012) Chembiochem , vol.13 , pp. 542-546
    • Zheng, J.S.1    Tang, S.2    Guo, Y.3    Chang, H.N.4    Liu, L.5
  • 29
    • 34548153495 scopus 로고    scopus 로고
    • Native chemical ligation at phenylalanine
    • D. Crich, and A. Banerjee Native chemical ligation at phenylalanine J. Am. Chem. Soc. 129 2007 10064 10065
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 10064-10065
    • Crich, D.1    Banerjee, A.2
  • 31
    • 54249149331 scopus 로고    scopus 로고
    • Native chemical ligation at valine: A contribution to peptide and glycopeptide synthesis
    • J. Chen, Q. Wan, Y. Yuan, J.L. Zhu, and S.J. Danishefsky Native chemical ligation at valine: a contribution to peptide and glycopeptide synthesis Angew. Chem. Int. Ed. 47 2008 8521 8524
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 8521-8524
    • Chen, J.1    Wan, Q.2    Yuan, Y.3    Zhu, J.L.4    Danishefsky, S.J.5
  • 32
    • 71049127491 scopus 로고    scopus 로고
    • Synthesis of 4-mercapto-l-lysine derivatives: Potential building blocks for sequential native chemical ligation
    • K.K. Pasunooti, R.L. Yang, S. Vedachalam, B.K. Gorityala, C.F. Liu, and X.W. Liu Synthesis of 4-mercapto-l-lysine derivatives: potential building blocks for sequential native chemical ligation Bioorg. Med. Chem. Lett. 19 2009 6268 6271
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 6268-6271
    • Pasunooti, K.K.1    Yang, R.L.2    Vedachalam, S.3    Gorityala, B.K.4    Liu, C.F.5    Liu, X.W.6
  • 34
    • 77956841522 scopus 로고    scopus 로고
    • Synthesis of K48-linked diubiquitin using dual native chemical ligation at lysine
    • R.L. Yang, K.K. Pasunooti, F.P. Li, X.W. Liu, and C.F. Liu Synthesis of K48-linked diubiquitin using dual native chemical ligation at lysine Chem. Commun. 46 2010 7199 7201
    • (2010) Chem. Commun. , vol.46 , pp. 7199-7201
    • Yang, R.L.1    Pasunooti, K.K.2    Li, F.P.3    Liu, X.W.4    Liu, C.F.5
  • 36
    • 77649190705 scopus 로고    scopus 로고
    • A program for ligation at threonine sites: Application to the controlled total synthesis of glycopeptides
    • J. Chen, P. Wang, J.L. Zhu, Q. Wan, and S.J. Danishefsky A program for ligation at threonine sites: application to the controlled total synthesis of glycopeptides Tetrahedron 66 2010 2277 2283
    • (2010) Tetrahedron , vol.66 , pp. 2277-2283
    • Chen, J.1    Wang, P.2    Zhu, J.L.3    Wan, Q.4    Danishefsky, S.J.5
  • 37
    • 77953463939 scopus 로고    scopus 로고
    • Protein synthesis assisted by native chemical ligation at leucine
    • Z. Harpaz, P. Siman, S.A. Kumar, and A. Brik Protein synthesis assisted by native chemical ligation at leucine Chembiochem 11 2010 1232 1235
    • (2010) Chembiochem , vol.11 , pp. 1232-1235
    • Harpaz, Z.1    Siman, P.2    Kumar, S.A.3    Brik, A.4
  • 38
    • 78650159619 scopus 로고    scopus 로고
    • Insights into the finer issues of native chemical ligation: An approach to cascade ligations
    • Z.P. Tan, S.Y. Shang, and S.J. Danishefsky Insights into the finer issues of native chemical ligation: an approach to cascade ligations Angew. Chem. Int. Ed. 49 2010 9500 9503
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 9500-9503
    • Tan, Z.P.1    Shang, S.Y.2    Danishefsky, S.J.3
  • 39
    • 79955027300 scopus 로고    scopus 로고
    • Application of the logic of cysteine-free native chemical ligation to the synthesis of human parathyroid hormone (hPTH), Dawson
    • S.Y. Shang, Z.P. Tan, and S.J. Danishefsky Application of the logic of cysteine-free native chemical ligation to the synthesis of human parathyroid hormone (hPTH), Dawson Proc. Natl. Acad. Sci. USA 108 2011 5986 5989
    • (2011) Proc. Natl. Acad. Sci. USA , vol.108 , pp. 5986-5989
    • Shang, S.Y.1    Tan, Z.P.2    Danishefsky, S.J.3
  • 42
    • 80054694198 scopus 로고    scopus 로고
    • Dual kinetically controlled native chemical ligation using a combination of sulfanylproline and sulfanylethylanilide peptide
    • H. Ding, A. Shigenaga, K. Sato, K. Morishita, and A. Otaka Dual kinetically controlled native chemical ligation using a combination of sulfanylproline and sulfanylethylanilide peptide Org. Lett. 13 2011 5588 5591
    • (2011) Org. Lett. , vol.13 , pp. 5588-5591
    • Ding, H.1    Shigenaga, A.2    Sato, K.3    Morishita, K.4    Otaka, A.5
  • 43
    • 84858691858 scopus 로고    scopus 로고
    • Native chemical ligation at glutamine
    • P. Siman, S.V. Karthikeyan, and A. Brik Native chemical ligation at glutamine Org. Lett. 14 2012 1520 1523
    • (2012) Org. Lett. , vol.14 , pp. 1520-1523
    • Siman, P.1    Karthikeyan, S.V.2    Brik, A.3
  • 45
    • 76949107715 scopus 로고    scopus 로고
    • Peptide ligation assisted by an auxiliary attached to amidyl nitrogen
    • J. Li, H.K. Cui, and L. Liu Peptide ligation assisted by an auxiliary attached to amidyl nitrogen Tetrahedron Lett. 51 2010 1793 1796
    • (2010) Tetrahedron Lett. , vol.51 , pp. 1793-1796
    • Li, J.1    Cui, H.K.2    Liu, L.3
  • 46
    • 84875002264 scopus 로고    scopus 로고
    • Peptide ligation-desulfurization chemistry at arginine
    • L.R. Malins, K.M. Cergol, and R.J. Payne Peptide ligation-desulfurization chemistry at arginine ChemBioChem 14 2013 559 563
    • (2013) ChemBioChem , vol.14 , pp. 559-563
    • Malins, L.R.1    Cergol, K.M.2    Payne, R.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.