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Angewandte Chemie - International Edition

Volumn 52, Issue 52, 2013, Pages 14001-14005

Enzymatic "click" ligation: Selective cysteine modification in polypeptides enabled by promiscuous glutathione S-transferase

(5) Zhang, Chi a Spokoyny, Alexander M a Zou, Yekui a Simon, Mark D a Pentelute, Bradley L a

a MASSACHUSETTS INSTITUTE OF TECHNOLOGY (United States)

Author keywords

bioconjugation; click chemistry; cysteine arylation; enzyme catalysis; peptide macrocyclization

Indexed keywords

ARYLATIONS; BIO-CONJUGATION; CLICK CHEMISTRY; ENZYME CATALYSIS; MACRO-CYCLIZATION;

AROMATIC COMPOUNDS; FUNCTIONAL GROUPS; PEPTIDES;

AMINO ACIDS;

CYSTEINE; GLUTATHIONE TRANSFERASE; PEPTIDE;

ARTICLE; BIOCONJUGATION; CATALYSIS; CHEMISTRY; CLICK CHEMISTRY; CYSTEINE ARYLATION; ENZYME CATALYSIS; HUMAN; PEPTIDE MACROCYCLIZATION; PROTEIN PROCESSING;

BIOCONJUGATION; CLICK CHEMISTRY; CYSTEINE ARYLATION; ENZYME CATALYSIS; PEPTIDE MACROCYCLIZATION;

CATALYSIS; CLICK CHEMISTRY; CYSTEINE; GLUTATHIONE TRANSFERASE; HUMANS; PEPTIDES; PROTEIN PROCESSING, POST-TRANSLATIONAL;

EID: 84890748670 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201306430 Document Type: Article

Times cited : (51)

References (67)

1
- 34547557995
- C. T. Walsh, S. Garneau-Tsodikova, G. J. Gatto, Angew. Chem. 2005, 117, 7508
- (2005) Angew. Chem. , vol.117 , pp. 7508
- Walsh, C.T.¹ Garneau-Tsodikova, S.² Gatto, G.J.³

2
- 28044433451
- Angew. Chem. Int. Ed. 2005, 44, 7342.
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 7342

3
- 1642434197
- B. G. Davis, Science 2004, 303, 480
- (2004) Science , vol.303 , pp. 480
- Davis, B.G.¹

4
- 80052516431
- L. Marchetti, M. Levine, ACS Catal. 2011, 1, 1090.
- (2011) ACS Catal. , vol.1 , pp. 1090
- Marchetti, L.¹ Levine, M.²

5
- 0000749443
- H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056
- (2001) Angew. Chem. , vol.113 , pp. 2056
- Kolb, H.C.¹ Finn, M.G.² Sharpless, K.B.³

6
- 0000096835
- Angew. Chem. Int. Ed. 2001, 40, 2004
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2004

7
- 77949863611
- J. C. Jewett, C. R. Bertozzi, Chem. Soc. Rev. 2010, 39, 1272-1279
- (2010) Chem. Soc. Rev. , vol.39 , pp. 1272-1279
- Jewett, J.C.¹ Bertozzi, C.R.²

8
- 34547272503
- J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249
- (2007) Chem. Soc. Rev. , vol.36 , pp. 1249
- Moses, J.E.¹ Moorhouse, A.D.²

9
- 70349973611
- C. R. Becer, R. Hoogenboom, U. S. Schubert, Angew. Chem. 2009, 121, 4998
- (2009) Angew. Chem. , vol.121 , pp. 4998
- Becer, C.R.¹ Hoogenboom, R.² Schubert, U.S.³

10
- 70349769688
- Angew. Chem. Int. Ed. 2009, 48, 4900
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 4900

11
- 53849105464
- M. L. Blackman, M. Royzen, J. M. Fox, J. Am. Chem. Soc. 2008, 130, 13518
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 13518
- Blackman, M.L.¹ Royzen, M.² Fox, J.M.³

12
- 77951214859
- C. E. Hoyle, C. N. Bowman, Angew. Chem. 2010, 122, 1584
- (2010) Angew. Chem. , vol.122 , pp. 1584
- Hoyle, C.E.¹ Bowman, C.N.²

13
- 77649122695
- Angew. Chem. Int. Ed. 2010, 49, 1540.
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 1540

14
- 84873292926
- C.-H. Wong, S. C. Zimmerman, Chem. Commun. 2013, 49, 1679.
- (2013) Chem. Commun. , vol.49 , pp. 1679
- Wong, C.-H.¹ Zimmerman, S.C.²

15
- 48049092838
- G. V. Los, L. P. Encell, M. G. McDougall, D. D. Hartzell, N. Karassina, C. Zimprich, M. G. Wood, R. Learish, R. F. Ohana, M. Urh, D. Simpson, J. Mendez, K. Zimmerman, P. Otto, G. Vidugiris, J. Zhu, A. Darzins, D. H. Klaubert, R. F. Bulleit, K. V. Wood, ACS Chem. Biol. 2008, 3, 373
- (2008) ACS Chem. Biol. , vol.3 , pp. 373
- Los, G.V.¹ Encell, L.P.² McDougall, M.G.³ Hartzell, D.D.⁴ Karassina, N.⁵ Zimprich, C.⁶ Wood, M.G.⁷ Learish, R.⁸ Ohana, R.F.⁹ Urh, M.¹⁰ Simpson, D.¹¹ Mendez, J.¹² Zimmerman, K.¹³ Otto, P.¹⁴ Vidugiris, G.¹⁵ Zhu, J.¹⁶ Darzins, A.¹⁷ Klaubert, D.H.¹⁸ Bulleit, R.F.¹⁹ Wood, K.V.²⁰ more..

16
- 78650350119
- S. Watanabe, S. Mizukami, Y. Hori, K. Kikuchi, Bioconjugate Chem. 2010, 21, 2320
- (2010) Bioconjugate Chem. , vol.21 , pp. 2320
- Watanabe, S.¹ Mizukami, S.² Hori, Y.³ Kikuchi, K.⁴

17
- 3242754218
- N. George, H. Pick, H. Vogel, N. Johnsson, K. Johnsson, J. Am. Chem. Soc. 2004, 126, 8896
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 8896
- George, N.¹ Pick, H.² Vogel, H.³ Johnsson, N.⁴ Johnsson, K.⁵

18
- 18744401100
- I. Chen, M. Howarth, W. Lin, A. Y. Ting, Nat. Methods 2005, 2, 99
- (2005) Nat. Methods , vol.2 , pp. 99
- Chen, I.¹ Howarth, M.² Lin, W.³ Ting, A.Y.⁴

19
- 77954633083
- C. Uttamapinant, K. A. White, H. Baruah, S. Thompson, M. Fernández-Suárez, S. Puthenveetil, A. Y. Ting, Proc. Natl. Acad. Sci. USA 2010, 107, 10914
- (2010) Proc. Natl. Acad. Sci. USA , vol.107 , pp. 10914
- Uttamapinant, C.¹ White, K.A.² Baruah, H.³ Thompson, S.⁴ Fernández- Suárez, M.⁵ Puthenveetil, S.⁶ Ting, A.Y.⁷

20
- 0037225952
- A. Keppler, S. Gendreizig, T. Gronemeyer, H. Pick, H. Vogel, K. Johnsson, Nat. Biotechnol. 2003, 21, 86
- (2003) Nat. Biotechnol. , vol.21 , pp. 86
- Keppler, A.¹ Gendreizig, S.² Gronemeyer, T.³ Pick, H.⁴ Vogel, H.⁵ Johnsson, K.⁶

21
- 84875213206
- L. S. Witus, M. Francis, Curr. Protoc. Chem. Biol. 2010, 2, 125
- (2010) Curr. Protoc. Chem. Biol. , vol.2 , pp. 125
- Witus, L.S.¹ Francis, M.²

22
- 35349018481
- M. W. Popp, J. M. Antos, G. M. Grotenbreg, E. Spooner, H. L. Ploegh, Nat. Chem. Biol. 2007, 3, 707.
- (2007) Nat. Chem. Biol. , vol.3 , pp. 707
- Popp, M.W.¹ Antos, J.M.² Grotenbreg, G.M.³ Spooner, E.⁴ Ploegh, H.L.⁵

23
- 77949880028
- A. Babtie, N. Tokuriki, F. Hollfelder, Curr. Opin. Chem. Biol. 2010, 14, 200
- (2010) Curr. Opin. Chem. Biol. , vol.14 , pp. 200
- Babtie, A.¹ Tokuriki, N.² Hollfelder, F.³

24
- 79959757238
- M. S. Humble, P. Berglund, Eur. J. Org. Chem. 2011, 3391
- (2011) Eur. J. Org. Chem. , pp. 3391
- Humble, M.S.¹ Berglund, P.²

25
- 77953623874
- O. Khersonsky, D. S. Tawfik, Annu. Rev. Biochem. 2010, 79, 471-505
- (2010) Annu. Rev. Biochem. , vol.79 , pp. 471-505
- Khersonsky, O.¹ Tawfik, D.S.²

26
- 79955594060
- M. T. Reetz, Angew. Chem. 2011, 123, 144
- (2011) Angew. Chem. , vol.123 , pp. 144
- Reetz, M.T.¹

27
- 78149432825
- Angew. Chem. Int. Ed. 2011, 50, 138
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 138

28
- 84872495336
- P. S. Coelho, E. M. Brustad, A. Kannan, F. H. Arnold, Science 2013, 339, 307.
- (2013) Science , vol.339 , pp. 307
- Coelho, P.S.¹ Brustad, E.M.² Kannan, A.³ Arnold, F.H.⁴

29
- 85013795111
- 2 nd ed., Elsevier, Amsterdam
- G. T. Hermanson, Bioconjugate Techniques, 2 nd ed., Elsevier, Amsterdam, 2008
- (2008) Bioconjugate Techniques
- Hermanson, G.T.¹

30
- 45749151511
- I. S. Carrico, Chem. Soc. Rev. 2008, 37, 1423
- (2008) Chem. Soc. Rev. , vol.37 , pp. 1423
- Carrico, I.S.¹

31
- 33744544685
- J. M. Antos, M. B. Francis, Curr. Opin. Chem. Biol. 2006, 10, 253
- (2006) Curr. Opin. Chem. Biol. , vol.10 , pp. 253
- Antos, J.M.¹ Francis, M.B.²

32
- 70349965066
- C. P. R. Hackenberger, D. Schwarzer, Angew. Chem. 2008, 120, 10182
- (2008) Angew. Chem. , vol.120 , pp. 10182
- Hackenberger, C.P.R.¹ Schwarzer, D.²

33
- 57749121492
- Angew. Chem. Int. Ed. 2008, 47, 10030
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 10030

34
- 77949546659
- E. Baslé, N. Joubert, M. Pucheault, Chem. Biol. 2010, 17, 213
- (2010) Chem. Biol. , vol.17 , pp. 213
- Baslé, E.¹ Joubert, N.² Pucheault, M.³

35
- 0027944205
- P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. H. Kent, Science 1994, 266, 776
- (1994) Science , vol.266 , pp. 776
- Dawson, P.E.¹ Muir, T.W.² Clark-Lewis, I.³ Kent, S.B.H.⁴

36
- 84890613293
- S. Sato, H. Nakamura, Angew. Chem. 2013, 125, 8843
- (2013) Angew. Chem. , vol.125 , pp. 8843
- Sato, S.¹ Nakamura, H.²

37
- 84882363599
- Angew. Chem. Int. Ed. 2013, 52, 8681
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 8681

38
- 84863533870
- J. J. Ling, R. L. Policarpo, A. E. Rabideau, X. Liao, B. L. Pentelute, J. Am. Chem. Soc. 2012, 134, 10749.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 10749
- Ling, J.J.¹ Policarpo, R.L.² Rabideau, A.E.³ Liao, X.⁴ Pentelute, B.L.⁵

39
- 67649130281
- J. M. Chalker, G. J. L. Bernardes, Y. A. Lin, B. G. Davis, Chem. Asian J. 2009, 4, 630
- (2009) Chem. Asian J. , vol.4 , pp. 630
- Chalker, J.M.¹ Bernardes, G.J.L.² Lin, Y.A.³ Davis, B.G.⁴

40
- 79957949748
- Wiley, New York
- "Modification of Cysteine": M. W. Crankshaw, G. A. Grant, Current Protocols in Protein Science, Wiley, New York, 1996.
- (1996) Current Protocols in Protein Science
- Cranksha, O.C.M.W.¹ Grant, G.A.²

41
- 0036276409
- M. N. Fodje, S. Al-Karadaghi, Protein Eng. 2002, 15, 353.
- (2002) Protein Eng. , vol.15 , pp. 353
- Fodje, M.N.¹ Al-Karadaghi, S.²

42
- 45549108466
- E. Weerapana, G. M. Simon, B. F. Cravatt, Nat. Chem. Biol. 2008, 4, 405.
- (2008) Nat. Chem. Biol. , vol.4 , pp. 405
- Weerapana, E.¹ Simon, G.M.² Cravatt, B.F.³

43
- 34247622775
- S. I. van Kasteren, H. B. Kramer, H. H. Jensen, S. J. Campbell, J. Kirkpatrick, N. J. Oldham, D. C. Anthony, B. G. Davis, Nature 2007, 446, 1105.
- (2007) Nature , vol.446 , pp. 1105
- Van Kasteren, S.I.¹ Kramer, H.B.² Jensen, H.H.³ Campbell, S.J.⁴ Kirkpatrick, J.⁵ Oldham, N.J.⁶ Anthony, D.C.⁷ Davis, B.G.⁸

44
- 0035977638
- L. Z. Yan, P. E. Dawson, J. Am. Chem. Soc. 2001, 123, 526
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 526
- Yan, L.Z.¹ Dawson, P.E.²

45
- 34548153495
- D. Crich, A. Banerjee, J. Am. Chem. Soc. 2007, 129, 10064
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 10064
- Crich, D.¹ Banerjee, A.²

46
- 53249109031
- Q. Wan, S. J. Danishefsky, Angew. Chem. 2007, 119, 9408
- (2007) Angew. Chem. , vol.119 , pp. 9408
- Wan, Q.¹ Danishefsky, S.J.²

47
- 37349094422
- Angew. Chem. Int. Ed. 2007, 46, 9248
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 9248

48
- 54249165628
- C. Haase, H. Rohde, O. Seitz, Angew. Chem. 2008, 120, 6912
- (2008) Angew. Chem. , vol.120 , pp. 6912
- Haase, C.¹ Rohde, H.² Seitz, O.³

49
- 52449084906
- Angew. Chem. Int. Ed. 2008, 47, 6807
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6807

50
- 57749113105
- J. Chen, Q. Wan, Y. Yuan, J. Zhu, S. J. Danishefsky, Angew. Chem. 2008, 120, 8649
- (2008) Angew. Chem. , vol.120 , pp. 8649
- Chen, J.¹ Wan, Q.² Yuan, Y.³ Zhu, J.⁴ Danishefsky, S.J.⁵

51
- 54249149331
- Angew. Chem. Int. Ed. 2008, 47, 8521
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 8521

52
- 42149123238
- G. J. Bernardes, J. M. Chalker, J. C. Errey, B. G. Davis, J. Am. Chem. Soc. 2008, 130, 5052
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 5052
- Bernardes, G.J.¹ Chalker, J.M.² Errey, J.C.³ Davis, B.G.⁴

53
- 33847791752
- B. L. Pentelute, S. B. H. Kent, Org. Lett. 2007, 9, 687.
- (2007) Org. Lett. , vol.9 , pp. 687
- Pentelute, B.L.¹ Kent, S.B.H.²

54
- 84876702107
- A. M. Spokoyny, Y. Zou, J. J. Ling, H. Yu, Y.-S. Lin, B. L. Pentelute, J. Am. Chem. Soc. 2013, 135, 5946.
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 5946
- Spokoyny, A.M.¹ Zou, Y.² Ling, J.J.³ Yu, H.⁴ Lin, Y.-S.⁵ Pentelute, B.L.⁶

55
- 66649091795
- C. R. Becer, K. Babiuch, D. Pilz, S. Hornig, T. Heinze, M. Gottschaldt, U. S. Schubert, Macromolecules 2009, 42, 2387.
- (2009) Macromolecules , vol.42 , pp. 2387
- Becer, C.R.¹ Babiuch, K.² Pilz, D.³ Hornig, S.⁴ Heinze, T.⁵ Gottschaldt, M.⁶ Schubert, U.S.⁷

56
- 12844268268
- J. D. Hayes, J. U. Flanagan, I. R. Jowsey, Annu. Rev. Pharmacol. Toxicol. 2005, 45, 51
- (2005) Annu. Rev. Pharmacol. Toxicol. , vol.45 , pp. 51
- Hayes, J.D.¹ Flanagan, J.U.² Jowsey, I.R.³

57
- 0031021397
- R. N. Armstrong, Chem. Res. Toxicol. 1997, 10, 2.
- (1997) Chem. Res. Toxicol. , vol.10 , pp. 2
- Armstrong, R.N.¹

58
- 84888995031
- T. Suzuki, Y. Ota, Y. Kasuya, M. Mutsuga, Y. Kawamura, H. Tsumoto, H. Nakagawa, M. G. Finn, N. Miyata, Angew. Chem. 2010, 122, 6969
- (2010) Angew. Chem. , vol.122 , pp. 6969
- Suzuki, T.¹ Ota, Y.² Kasuya, Y.³ Mutsuga, M.⁴ Kawamura, Y.⁵ Tsumoto, H.⁶ Nakagawa, H.⁷ Finn, M.G.⁸ Miyata, N.⁹

59
- 77956609618
- Angew. Chem. Int. Ed. 2010, 49, 6817.
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 6817

60
- 58149099860
- A. Dirksen, P. E. Dawson, Bioconjugate Chem. 2008, 19, 2543.
- (2008) Bioconjugate Chem. , vol.19 , pp. 2543
- Dirksen, A.¹ Dawson, P.E.²

61
- 61349194032
- T. Kurpiers, H. D. Mootz, Angew. Chem. 2007, 119, 5327
- (2007) Angew. Chem. , vol.119 , pp. 5327
- Kurpiers, T.¹ Mootz, H.D.²

62
- 34447329908
- Angew. Chem. Int. Ed. 2007, 46, 5234
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5234

63
- 84886858982
- R. I. Nathani, P. Moody, V. Chudasama, M. E. B. Smith, R. J. Fitzmaurice, S. Caddick, Chem. Sci. 2013, 4, 3455.
- (2013) Chem. Sci. , vol.4 , pp. 3455
- Nathani, R.I.¹ Moody, P.² Chudasama, V.³ Smith, M.E.B.⁴ Fitzmaurice, R.J.⁵ Caddick, S.⁶

64
- 46449115901
- E. M. Driggers, S. P. Hale, J. Lee, N. K. Terrett, Nat. Rev. Drug Discovery 2008, 7, 608.
- (2008) Nat. Rev. Drug Discovery , vol.7 , pp. 608
- Driggers, E.M.¹ Hale, S.P.² Lee, J.³ Terrett, N.K.⁴

65
- 79959580534
- C. J. White, A. K. Yudin, Nat. Chem. 2011, 3, 509.
- (2011) Nat. Chem. , vol.3 , pp. 509
- White, C.J.¹ Yudin, A.K.²

66
- 0023687171
- A. E. Adang, J. Brussee, D. J. Meyer, B. Coles, B. Ketterer, A. van der Gen, G. J. Mulder, Biochem. J. 1988, 255, 721
- (1988) Biochem. J. , vol.255 , pp. 721
- Adang, A.E.¹ Brussee, J.² Meyer, D.J.³ Coles, B.⁴ Ketterer, B.⁵ Van Der Gen, A.⁶ Mulder, G.J.⁷

67
- 0025340142
- A. E. Adang, J. Brussee, A. van der Gen, G. J. Mulder, Biochem. J. 1990, 269, 47.
- (1990) Biochem. J. , vol.269 , pp. 47
- Adang, A.E.¹ Brussee, J.² Van Der Gen, A.³ Mulder, G.J.⁴

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