Skip to main content
SpringerLink
Log in

Thioamide-Containing Peptides and Proteins

  • Chapter
  • First Online:
Chemistry of Thioamides

Abstract

Thioamidation of the peptide backbone can have both subtle and profound effects on peptide and protein properties. Oxoamide-to-thioamide substitutions can alter hydrogen bonding networks, metal interactions, peptide folding, and photophysical properties. Thioamides are found in a small number of natural products with intriguing antibiotic and anticancer activities. A thioamide residue is also found in a natural protein that is essential to biological methane metabolism. Recent genetic scanning has shed light on the biosynthesis of these molecules and indicated that many other thioamide-containing peptides and proteins exist. Thioamide modifications have been installed synthetically to investigate the biosynthesis and biological activity of these thioamide natural products, as well as to serve as biophysical probes or to enhance the stability and activity of medicinally relevant peptides. The synthesis of these molecules has required the development of methods for the incorporation of thioamides by solid-phase peptide synthesis and through native chemical ligation of protein fragments. The expanding number of known thioamide natural products, the ability to gain detailed insights into protein folding mechanisms, and recent demonstrations of valuable in vivo activity for thioamide-modified peptides highlight the impact of thioamides in peptide and protein chemistry.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. A. Choudhary, R.T. Raines, ChemBioChem 12, 1801 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Nomenclature and symbolism for amino acids and peptides. Eur. J. Biochem. 138, 9 (1984)

    Google Scholar 

  3. T. Sifferlen, M. Rueping, K. Gademann, B. Jaun, D. Seebach, Helv. Chim. Acta 82, 2067 (1999)

    Article  CAS  Google Scholar 

  4. F.G. Bordwell, D.J. Algrim, J.A. Harrelson, J. Am. Chem. Soc. 110, 5903 (1988)

    Article  CAS  Google Scholar 

  5. K.B. Wiberg, D.J. Rush, J. Am. Chem. Soc. 123, 2038 (2001)

    Article  CAS  PubMed  Google Scholar 

  6. M. Hollósi, Z. Majer, M. Zewdu, F. Ruff, M. Kajtár, K.E. Kövér, Tetrahedron 44, 195 (1988)

    Article  Google Scholar 

  7. E.P. Dudek, G.O. Dudek, J. Org. Chem. 32, 823 (1967)

    Article  CAS  Google Scholar 

  8. H.-J. Lee, Y.-S. Choi, K.-B. Lee, J. Park, C.-J. Yoon, J. Phys. Chem. A 106, 7010 (2002)

    Article  CAS  Google Scholar 

  9. T.S. Jagodzinski, Chem. Rev. 103, 197 (2003)

    Article  PubMed  CAS  Google Scholar 

  10. T.F.M. La Cour, H.a.S. Hansen, K.I.M. Clausen, S.O. Lawesson, Int. J. Pept. Protein Sci. 22, 509 (1983)

    Google Scholar 

  11. S.K. Misra, U.C. Tewari, Transition Met. Chem. 27, 120 (2002)

    Article  CAS  Google Scholar 

  12. J. Helbing et al., J. Am. Chem. Soc. 126, 8823 (2004)

    Article  CAS  PubMed  Google Scholar 

  13. E.J. Petersson, J.M. Goldberg, R.F. Wissner, Phys. Chem. Chem. Phys. 16, 6827 (2014)

    Article  CAS  PubMed  Google Scholar 

  14. M. Pan, T.J. Mabry, J.M. Beale, B.M. Mamiyat, Phytochemistry 45, 517 (1997)

    Article  CAS  PubMed  Google Scholar 

  15. N. Yutin, M.Y. Galperin, Environ. Microbiol. 15, 2631 (2013)

    CAS  PubMed  PubMed Central  Google Scholar 

  16. T. Lincke, S. Behnken, K. Ishida, M. Roth, C. Hertweck, Angew. Chem. Int. Ed. 49, 2011 (2010)

    Google Scholar 

  17. S. Behnken, T. Lincke, F. Kloss, K. Ishida, C. Hertweck, Angew. Chem. Int. Ed. 51, 2425 (2012)

    Article  CAS  PubMed  Google Scholar 

  18. K.L. Dunbar, H. Büttner, E.M. Molloy, M. Dell, J. Kumpfmüller, C. Hertweck, Angew. Chem. Int. Ed. 57, 14080 (2018)

    Article  CAS  PubMed  Google Scholar 

  19. P.G. Arnison et al., Nat. Prod. Rep. 30, 108 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. J.D. Semrau et al., Environ. Microbiol. 15, 3077 (2013)

    CAS  PubMed  Google Scholar 

  21. H.J. Kim et al., Science 305, 1612 (2004)

    Article  CAS  PubMed  Google Scholar 

  22. Y. Hayakawa, K. Sasaki, H. Adachi, K. Furihata, K. Shin-Ya, K. Nagai, J. Antibiot. 59, 1 (2006)

    Article  CAS  Google Scholar 

  23. Y. Hayakawa, K. Sasaki, K. Nagai, K. Shin-Ya, K. Furihata, J. Antibiot. 59, 6 (2006)

    Article  CAS  Google Scholar 

  24. M. Izumikawa et al., J. Antibiot. 68, 533 (2015)

    Article  CAS  Google Scholar 

  25. L. Kjaerulff, A. Sikandar, N. Zaburannyi, S. Adam, J. Herrmann, J. Koehnke, R. Müller, ACS Chem. Biol. 12, 2837 (2017)

    Article  CAS  PubMed  Google Scholar 

  26. L. Frattaruolo, R. Lacret, A.R. Cappello, A.W. Truman, ACS Chem. Biol. 12, 2815 (2017)

    Article  CAS  PubMed  Google Scholar 

  27. T. Kawahara et al., J. Nat. Prod. 81, 264 (2018)

    Article  CAS  PubMed  Google Scholar 

  28. U. Ermler, W. Grabarse, S. Shima, M. Goubeaud, R.K. Thauer, Science 278, 1457 (1997)

    Google Scholar 

  29. J. Kahnt, B. Buchenau, F. Mahlert, M. Krüger, S. Shima, R.K. Thauer, FEBS J. 274, 4913 (2007)

    Article  CAS  PubMed  Google Scholar 

  30. W. Grabarse, F. Mahlert, S. Shima, R.K. Thauer, U. Ermler, J. Mol. Biol. 303, 329 (2000)

    Article  CAS  PubMed  Google Scholar 

  31. D.D. Nayak, N. Mahanta, D.A. Mitchell, W.W. Metcalf, eLIFE (2017)

    Google Scholar 

  32. B.J. Burkhart, C.J. Schwalen, G. Mann, J.H. Naismith, D.A. Mitchell, Chem. Rev. 117, 5389 (2017)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. M. Izawa, T. Kawasaki, Y. Hayakawa, Appl. Environ. Microbiol. 79, 7110 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. B.T. Breil, J. Borneman, E.W. Triplett, J. Bacteriol. 178, 4150 (1996)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  35. K.L. Dunbar, J.R. Chekan, C.L. Cox, B.J. Burkhart, S.K. Nair, D.A. Mitchell, Nat. Chem. Biol. 10, 823 (2014)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  36. N. Mahanta, A. Liu, S. Dong, S.K. Nair, D.A. Mitchell, Proc. Natl. Acad. Sci. USA 115, 3030 (2018)

    Google Scholar 

  37. C.J. Schwalen, G.A. Hudson, B. Kille, D.A. Mitchell, J. Am. Chem. Soc. 140, 9494 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. G.E. Kenney, A.C. Rosenzweig, BMC Biol. 11 (2013)

    Google Scholar 

  39. G.E. Kenney et al., Science 359, 1411 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. V.V. Richter, in Chemistry of the Carbon Compounds (P. Blakiston, son & co., Philadelphia, 1886)

    Google Scholar 

  41. R.N. Hurd, G. Delamater, Chem. Rev. 61, 45 (1961)

    Article  CAS  Google Scholar 

  42. J.W. Scheeren, P.H.J. Ooms, R.J.F. Nivard, Synthesis 149 (1973)

    Google Scholar 

  43. S. Scheibye, B.S. Pedersen, S.O. Lawesson, B. Soc. Chim. Belg. 87, 229 (1978)

    Google Scholar 

  44. T. Guntreddi, R. Vanjari, K.N. Singh, Tetrahedron 70, 3887 (2014)

    Article  CAS  Google Scholar 

  45. B. Kaboudin, V. Yarahmadi, J. Kato, T. Yokomatsu, RSC Adv. 3, 6435 (2013)

    Article  CAS  Google Scholar 

  46. M. Muhlberg, K.D. Siebertz, B. Schlegel, P. Schmieder, C.P.R. Hackenberger, Chem. Commun. 50, 4603 (2014)

    Article  PubMed  CAS  Google Scholar 

  47. A. Pourvali, J.R. Cochrane, C.A. Hutton, Chem. Commun. 50, 15963 (2014)

    Article  CAS  Google Scholar 

  48. Y.D. Sun, H.F. Jiang, W.Q. Wu, W. Zeng, J.X. Li, Org. Biomol. Chem. 12, 700 (2014)

    Article  CAS  PubMed  Google Scholar 

  49. X. Wang, M. Ji, S. Lim, H.Y. Jang, J. Org. Chem. 79, 7256 (2014)

    Article  CAS  PubMed  Google Scholar 

  50. A.K. Yadav, V.P. Srivastava, L.D.S. Yadav, Tetrahedron Lett. 53, 7113 (2012)

    Article  CAS  Google Scholar 

  51. U. Pathak, S. Bhattacharyya, S. Mathur, RSC Adv. 5, 4484 (2015)

    Article  CAS  Google Scholar 

  52. B.V. Varun, A. Sood, K.R. Prabhu, RSC Adv. 4, 60798 (2014)

    Article  CAS  Google Scholar 

  53. H.L. Xu, H. Deng, Z.K. Li, H.F. Xiang, X.G. Zhou, Eur. J. Biochem. 2013, 7054 (2013)

    CAS  Google Scholar 

  54. J. Bergman, B. Pettersson, V. Hasimbegovic, P.H. Svensson, J. Org. Chem. 76, 1546 (2011)

    Article  CAS  PubMed  Google Scholar 

  55. S.V. Ley, A.G. Leach, R.I. Storer, J. Chem. Soc. Perkin 1, 358 (2001)

    Google Scholar 

  56. Z. Kaleta, B.T. Makowski, T. Soos, R. Dembinski, Org. Lett. 8, 1625 (2006)

    Article  CAS  PubMed  Google Scholar 

  57. Z. Kaleta, G. Tarkanyi, A. Gomory, F. Kalman, T. Nagy, T. Soos, Org. Lett. 8, 1093 (2006)

    Article  CAS  PubMed  Google Scholar 

  58. E.S. Gatewood, T.P. Johnson, J. Am. Chem. Soc. 48, 2900 (1926)

    Article  CAS  Google Scholar 

  59. W.C. Jones, J.J. Nestor, V. Du Vigneaud, J. Am. Chem. Soc. 95, 5677 (1973)

    Article  CAS  PubMed  Google Scholar 

  60. O.E. Jensen, S.O. Lawesson, R. Bardi, A.M. Piazzesi, C. Toniolo, Tetrahedron 41, 5595 (1985)

    Article  CAS  Google Scholar 

  61. J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 54, 8721 (1998)

    Article  CAS  Google Scholar 

  62. J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 55, 5359 (1999)

    Article  CAS  Google Scholar 

  63. N. Shangguan, S. Katukojvala, R. Greenberg, L.J. Williams, J. Am. Chem. Soc. 125, 7754 (2003)

    Article  CAS  PubMed  Google Scholar 

  64. M. Mühlberg, K.D. Siebertz, B. Schlegel, P. Schmieder, C.P.R. Hackenberger, Chem. Commun. 50, 4603 (2014)

    Article  PubMed  CAS  Google Scholar 

  65. T. Hoegjensen, M.H. Jakobsen, C.E. Olsen, A. Holm, Tetrahedron Lett. 32, 7617 (1991)

    Article  CAS  Google Scholar 

  66. H.T. Le, J.F. Gallard, M. Mayer, E. Guittet, R. Michelot, Bioorg. Med. Chem. 4, 2201 (1996)

    Article  CAS  PubMed  Google Scholar 

  67. B. Zacharie, R. Martel, G. Sauve, B. Belleau, Bioorg. Med. Chem. Lett. 3, 619 (1993)

    Article  CAS  Google Scholar 

  68. B. Zacharie, M. Lagraoui, M. Dimarco, C.L. Penney, L. Gagnon, J. Med. Chem. 42, 2046 (1999)

    Article  CAS  PubMed  Google Scholar 

  69. C.T. Brain, A. Hallett, S.Y. Ko, J. Org. Chem. 62, 3808 (1997)

    Article  CAS  Google Scholar 

  70. S. Batjargal, Y. Huang, Y.J. Wang, E.J. Petersson, J. Pept. Sci. 20, 87 (2014)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  71. S. Batjargal, Y.J. Wang, J.M. Goldberg, R.F. Wissner, E.J. Petersson, J. Am. Chem. Soc. 134, 9172 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  72. J.M. Goldberg, S. Batjargal, B.S. Chen, E.J. Petersson, J. Am. Chem. Soc. 135, 18651 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  73. J.M. Goldberg, S. Batjargal, E.J. Petersson, J. Am. Chem. Soc. 132, 14718 (2010)

    Article  CAS  PubMed  Google Scholar 

  74. J.M. Goldberg, X. Chen, N. Meinhardt, D.C. Greenbaum, E.J. Petersson, J. Am. Chem. Soc. 136, 2086 (2014)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  75. J.M. Goldberg, L.C. Speight, M.W. Fegley, E.J. Petersson, J. Am. Chem. Soc. 134, 6088 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  76. J.M. Goldberg, R.F. Wissner, A.M. Klein, E.J. Petersson, Chem. Commun. 48, 1550 (2012)

    Article  CAS  Google Scholar 

  77. R.F. Wissner, S. Batjargal, C.M. Fadzen, E.J. Petersson, J. Am. Chem. Soc. 135, 6529 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  78. R.F. Wissner, A.M. Wagner, J.B. Warner, E.J. Petersson, Synlett 24, 2454 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  79. S. Mukherjee, J. Chatterjee, J. Pept. Sci. 22, 664 (2016)

    Article  CAS  PubMed  Google Scholar 

  80. S. Mukherjee, H. Verma, J. Chatterjee, Org. Lett. 17, 3150 (2015)

    Article  CAS  PubMed  Google Scholar 

  81. H. Verma, B. Khatri, S. Chakraborti, J. Chatterjee, Chem. Sci. 9, 2443 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  82. J.H. Miwa, L. Pallivathucal, S. Gowda, K.E. Lee, Org. Lett. 4, 4655 (2002)

    Article  CAS  PubMed  Google Scholar 

  83. J.H. Miwa, A.K. Patel, N. Vivatrat, S.M. Popek, A.M. Meyer, Org. Lett. 3, 3373 (2001)

    Article  CAS  PubMed  Google Scholar 

  84. X. Chen et al., J. Am. Chem. Soc. 139, 16688 (2017)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  85. C.R. Walters, D.M. Szantai-Kis, Y. Zhang, Z.E. Reinert, W.S. Horne, D.M. Chenoweth, E.J. Petersson, Chem. Sci. 8, 2868 (2017)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  86. D.M. Szantai-Kis, C.R. Walters, T.M. Barrett, E.M. Hoang, E.J. Petersson, Synlett 28, 1789 (2017)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  87. C. Unverzagt, A. Geyer, H. Kessler, Angew. Chem. Int. Ed. 31, 1229 (1992)

    Google Scholar 

  88. K.L. Dunbar, D.A. Mitchell, J. Am. Chem. Soc. 135, 8692 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  89. S. Kent, Y. Sohma, S. Liu, D. Bang, B. Pentelute, K. Mandal, J. Pept. Sci. 18, 428 (2012)

    Article  CAS  PubMed  Google Scholar 

  90. C.T.T. Wong, C.L. Tung, X. Li, Mol. Biosyst. 9, 826–833 (2013)

    Article  CAS  PubMed  Google Scholar 

  91. D. Wildemann, C. Schiene-Fischer, T. Aumüller, A. Bachmann, T. Kiefhaber, C. Lücke, G. Fischer, J. Am. Chem. Soc. 129, 4910 (2007)

    Article  CAS  PubMed  Google Scholar 

  92. J. Kang, D. Macmillan, Org. Biomol. Chem. 8, 1993 (2010)

    Article  CAS  PubMed  Google Scholar 

  93. T. Kawakami, S. Shimizu, S. Aimoto, J. Pept. Sci. 16, 50 (2010)

    Google Scholar 

  94. J.B. Blanco-Canosa, P.E. Dawson, Angew. Chem. Int. Ed. 47, 6851 (2008)

    Article  CAS  PubMed  Google Scholar 

  95. P. Grieco, P.M. Gitu, V.J. Hruby, J. Pept. Res. 57, 250 (2001)

    Google Scholar 

  96. S.K. Mahto, C.J. Howard, J.C. Shimko, J.J. Ottesen, ChemBioChem 12, 2488 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  97. P. Botti, M. Villain, S. Manganiello, H. Gaertner, Org. Lett. 6, 4861 (2004)

    Article  CAS  PubMed  Google Scholar 

  98. E.A. George, R.P. Novick, T.W. Muir, J. Am. Chem. Soc. 130, 4914 (2008)

    Article  CAS  PubMed  Google Scholar 

  99. Y.J. Wang, in Chemical Modification Methods for Protein Misfolding Studies (University of Pennsylvania, Pennsylvania, 2015)

    Google Scholar 

  100. J.-S. Zheng, S. Tang, Y.-K. Qi, Z.-P. Wang, L. Liu, Nat. Protoc. 8, 2483 (2013)

    Article  CAS  PubMed  Google Scholar 

  101. D. Bang, B.L. Pentelute, S.B. Kent, Angew. Chem. Int. Ed. 45, 3985 (2006)

    Article  CAS  PubMed  Google Scholar 

  102. V. Muralidharan, T.W. Muir, Nat. Methods 3, 429 (2006)

    Article  CAS  PubMed  Google Scholar 

  103. C.R. Walters, J.J. Ferrie, E.J. Petersson, Chem. Commun. 54, 1766 (2018)

    Article  CAS  Google Scholar 

  104. L.R. Malins, R.J. Payne, Curr. Opin. Chem. Biol. 22, 70 (2014)

    Google Scholar 

  105. Y.J. Wang, D.M. Szantai-Kis, E.J. Petersson, Org. Biomol. Chem. 14, 6262 (2016)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  106. J. Chen, Q. Wan, Y. Yuan, J. Zhu, S.J. Danishefsky, Angew. Chem. Int. Ed. 47, 8521 (2008)

    Article  CAS  PubMed  Google Scholar 

  107. M.A. Raftery, R.D. Cole, J. Biol. Chem. 241, 3457 (1966)

    CAS  PubMed  Google Scholar 

  108. S. Marincean, M. Rabago Smith, L. Beltz, B. Borhan, J. Mol. Model 18, 4547 (2012)

    Google Scholar 

  109. A. Aitken, M. Learmonth, Carboxymethylation of cysteine using iodoacetamide/iodoacetic acid, in The Protein Protocols Handbook, ed. by J.M. Walker (Humana Press, Totowa, NJ, 2002), p. 455. https://doi.org/10.1385/1-59259-169-8:455

  110. Q.-Q. He, G.-M. Fang, L. Liu, Chin. Chem. Lett. 24, 265 (2013)

    Article  CAS  Google Scholar 

  111. T. Tanaka, A.M. Wagner, J.B. Warner, Y.J. Wang, E.J. Petersson, Angew. Chem. Int. Ed. 52, 6210 (2013)

    Google Scholar 

  112. R.E. Connor, K. Piatkov, A. Varshavsky, D.A. Tirrell, ChemBioChem 9, 366 (2008)

    Article  CAS  PubMed  Google Scholar 

  113. E. Graciet, R.G. Hu, K. Piatkov, J.H. Rhee, E.M. Schwarz, A. Varshavsky, Proc. Natl. Acad. Sci. USA 103, 3078 (2006)

    Google Scholar 

  114. A. Varshavsky, Nat. Struct. Mol. Biol. 15, 1238 (2008)

    Google Scholar 

  115. S. Dery, P.S. Reddy, L. Dery, R. Mousa, R.N. Dardashti, N. Metanis, Chem. Sci. 6, 6207 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  116. J. Liu, F. Zheng, R. Cheng, S. Li, S. Rozovsky, Q. Wang, L. Wang, J. Am. Chem. Soc. 140, 8807 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  117. H. Xiong, N.M. Reynolds, C.G. Fan, M. Englert, D. Hoyer, S.J. Miller, D. Soll, Angew. Chem. Int. Ed. 55, 4083 (2016)

    Article  CAS  PubMed  Google Scholar 

  118. F. Kloss, S. Pidot, H. Goerls, T. Friedrich, C. Hertweck, Angew. Chem. Int. Ed. 52, 10745 (2013)

    Article  CAS  PubMed  Google Scholar 

  119. F. Kloss, A.I. Chiriac, C. Hertweck, Chem. Eur. J. 20, 15451 (2014)

    Article  CAS  PubMed  Google Scholar 

  120. A.I. Chiriac, F. Kloss, J. Krämer, C. Vuong, C. Hertweck, H.-G. Sahl, J. Antimicrob. Chemother. 70, 2576 (2015)

    Article  CAS  PubMed  Google Scholar 

  121. K. Manzor, K.Ó. Proinsias, F. Kelleher, Tetrahedron Lett. 58, 2959 (2017)

    Article  CAS  Google Scholar 

  122. M. De Zotti et al., Beilstein J. Org. Chem. 8, 1161 (2012)

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  123. K.R. Wang, B.Z. Zhang, W. Zhang, J.X. Yan, J. Li, R. Wang, Peptides 29, 963 (2008)

    Article  CAS  PubMed  Google Scholar 

  124. W. Zhang, J. Li, L.W. Liu, K.R. Wang, J.J. Song, J.X. Yan, Peptides 31, 1832 (2010)

    Article  CAS  PubMed  Google Scholar 

  125. A. Chevalier, C. Massif, P.Y. Renard, A. Romieu, Chem. Eur. J. 19, 1686 (2013)

    Article  CAS  PubMed  Google Scholar 

  126. M.-M. Carlos, R. Florian, A. Horst, Anti-Cancer Agents Med. Chem. 10, 753 (2010)

    Article  Google Scholar 

  127. J.-P. Xiong, T. Stehle, R. Zhang, A. Joachimiak, M. Frech, S.L. Goodman, M.A. Arnaout, Science 296, 151 (2002)

    Article  CAS  PubMed  Google Scholar 

  128. J.E. Bock, J. Gavenonis, J.A. Kritzer, ACS Chem. Biol. 8, 488 (2013)

    Article  CAS  PubMed  Google Scholar 

  129. J.S. Laursen, J. Engel-Andreasen, P. Fristrup, P. Harris, C.A. Olsen, J. Am. Chem. Soc. 135, 2835 (2013)

    Article  CAS  PubMed  Google Scholar 

  130. R.W. Newberry, B. Vanveller, I.A. Guzei, R.T. Raines, J. Am. Chem. Soc. 135, 7843 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  131. R.W. Newberry, B. Vanveller, R.T. Raines, Chem. Commun. 51, 9624 (2015)

    Article  CAS  Google Scholar 

  132. B.C. Gorske, R.C. Nelson, Z.S. Bowden, T.A. Kufe, A.M. Childs, J. Org. Chem. 78, 11172 (2013)

    Article  CAS  PubMed  Google Scholar 

  133. A. Okano, R.C. James, J.G. Pierce, J. Xie, D.L. Boger, J. Am. Chem. Soc. 134, 8790 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  134. B.M. Crowley, D.L. Boger, J. Am. Chem. Soc. 128, 2885 (2006)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  135. A. Okano, A. Nakayama, A.W. Schammel, D.L. Boger, J. Am. Chem. Soc. 136, 13522 (2014)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  136. J. Xie, A. Okano, J.G. Pierce, R.C. James, S. Stamm, C.M. Crane, D.L. Boger, J. Am. Chem. Soc. 134, 1284 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  137. A. Okano, N.A. Isley, D.L. Boger, Proc. Natl. Acad. Sci. USA 114, E5052 (2017)

    Google Scholar 

  138. K.C. Nicolaou et al., J. Am. Chem. Soc. 127, 11159 (2005)

    Article  CAS  PubMed  Google Scholar 

  139. C.R. Walters, J.J. Ferrie, E.J. Petersson, Thioamide labeling of proteins through a combination of semisynthetic methods, in Chemical Ligation: Tools for Biomolecule Synthesis and Modification, ed. by L.D. D’Andrea, A. Romanelli, 2nd edn. (Wiley, Hoboken, 2017), p. 355

    Chapter  Google Scholar 

  140. M. Hollósi, E. Kollát, J. Kajtár, M. Kajtár, G.D. Fasman, Biopolymers 30, 1061 (1990)

    Article  Google Scholar 

  141. R. Frank, M. Jakob, F. Thunecke, G. Fischer, M. Schutkowski, Angew. Chem. Int. Ed. 39, 1120 (2000)

    Article  CAS  PubMed  Google Scholar 

  142. J. Zhao, J.-C. Micheau, C. Vargas, C. Schiene-Fischer, Chem. Eur. J. 10, 6093 (2004)

    Article  CAS  PubMed  Google Scholar 

  143. Y. Huang, Z. Cong, L. Yang, S. Dong, J. Pept. Sci. 14, 1062 (2008)

    Article  CAS  PubMed  Google Scholar 

  144. W.M. Wiczk, I. Gryczynski, H. Szmacinski, M.L. Johnson, M. Kruszynski, J. Zboinska, J. Biophys. Chem. 32, 43 (1988)

    Article  CAS  Google Scholar 

  145. Y. Huang, J.J. Ferrie, X. Chen, Y. Zhang, D.M. Szantai-Kis, D.M. Chenoweth, E.J. Petersson, Chem. Commun. 52, 7798 (2016)

    Article  CAS  Google Scholar 

  146. S.H.L. Verhelst, FEBS J. 284, 1489 (2017)

    Article  CAS  PubMed  Google Scholar 

  147. M. Drag, G.S. Salvesen, Nat. Rev. Drug Discov. 9, 690 (2010)

    Google Scholar 

  148. P.A. Bartlett, K.L. Spear, N.E. Jacobsen, Biochemistry 21, 1608 (1982)

    Article  CAS  PubMed  Google Scholar 

  149. P. Campbell, N.T. Nashed, J. Am. Chem. Soc. 104, 5221 (1982)

    Article  CAS  Google Scholar 

  150. M.D. Bond, B. Holmquist, B.L. Vallee, J. Inorg. Biochem. 28, 97 (1986)

    Article  CAS  PubMed  Google Scholar 

  151. W.L. Mock, J.-T. Chen, J.W. Tsang, Biochem. Biophys. Res. Commun. 102, 389 (1981)

    Google Scholar 

  152. K. Cho, Anal. Biochem. 164, 248 (1987)

    Google Scholar 

  153. M. Roberts, D. Guthrie, C. Williams, S. Martin, in The Effects of Several Aminopeptidases Towards Thionopeptides (Portland Press Limited, 1994)

    Google Scholar 

  154. K.L. Foje, R.P. Hanzlik, Biochim. Biophys. Acta Gen. Subj. 1201, 447 (1994)

    Google Scholar 

  155. M. Schutkowski, K. Neubert, G. Fischer, Eur. J. Biochem. 221, 455 (1994)

    Article  CAS  PubMed  Google Scholar 

  156. A. Kathleen et al., Protein Sci. 13, 412 (2004)

    Article  CAS  Google Scholar 

  157. G. Lowe, Y. Yuthavong, Biochem. J. 124, 107 (1971)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  158. S.A. Thompson, P.R. Andrews, R.P. Hanzlik, J. Med. Chem. 29, 104 (1986)

    Article  CAS  PubMed  Google Scholar 

  159. J.C. Kelly, D. Cuerrier, L.A. Graham, R.L. Campbell, P.L. Davies, Biochim. Biophys. Acta Proteins Proteomics 1794, 1505 (2009)

    Google Scholar 

  160. R.E. Beattie, C.H. Williams, D.T. Elmore, in L-Leucine Thioamide as an Inhibitor of Leucine Aminopeptidase (Portland Press Limited, 1988)

    Google Scholar 

  161. J. Mcelroy, D.J. Guthrie, N.M. Hooper, C.H. Williams, in 40 gly-(csnh)-phe Resists Hydrolysis by Membrane Dipeptidase (Portland Press Limited, 1998)

    Google Scholar 

  162. A. Stöckel-Maschek, C. Mrestani-Klaus, B. Stiebitz, H.-U. Demuth, K. Neubert, Biochim. Biophys. Acta Protein Struct. 1479, 15 (2000)

    Google Scholar 

  163. S. Yao, R. Zutshi, J. Chmielewski, Bioorg. Med. Chem. Lett. 8, 699 (1998)

    Article  CAS  PubMed  Google Scholar 

  164. M. Schutkowski, M. Jakob, G. Landgraf, I. Born, K. Neubert, G. Fischer, Eur. J. Biochem. 245, 381 (1997)

    Article  CAS  PubMed  Google Scholar 

  165. A.A. Kaspar, J.M. Reichert, Drug. Discov. Today 18, 807 (2013)

    Article  CAS  PubMed  Google Scholar 

  166. K. Fosgerau, T. Hoffmann, Drug. Discov. Today 20, 122 (2015)

    Article  CAS  PubMed  Google Scholar 

  167. L. Gentilucci, R. De Marco, L. Cerisoli, Curr. Pharm. Design 16, 3185 (2010)

    Article  CAS  Google Scholar 

  168. J.H. Weiss, D.W. Choi, Science 241, 973 (1988)

    Article  CAS  PubMed  Google Scholar 

  169. G. Pasut, F.M. Veronese, J. Control. Release 161, 461 (2012)

    Article  CAS  PubMed  Google Scholar 

  170. J.K. Dozier, M.D. Distefano, Int. J. Mol. Sci. 16, 25831 (2015)

    Google Scholar 

  171. B.D. Larsen, in Pharmacologically Active Peptide Conjugates Having a Reduced Tendency Towards Enzymatic Hydrolysis (Google Patents, 2008)

    Google Scholar 

  172. M.E. Houston, A.P. Campbell, B. Lix, C.M. Kay, B.D. Sykes, R.S. Hodges, Biochemistry 35, 10041 (1996)

    Article  CAS  PubMed  Google Scholar 

  173. P. Timmerman et al., Open Vaccine J. 2, 56 (2009)

    Article  CAS  Google Scholar 

  174. S. Sim, Y. Kim, T. Kim, S. Lim, M. Lee, J. Am. Chem. Soc. 134, 20270 (2012)

    Article  CAS  PubMed  Google Scholar 

  175. A.O. Subtelny, M.C. Hartman, J.W. Szostak, J. Am. Chem. Soc. 130, 6131 (2008)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  176. J.-K. Bang, Y.-H. Nan, E.-K. Lee, S.-Y. Shin, Bull. Korean Chem. Soc. 31, 2509 (2010)

    Google Scholar 

  177. P. Claudon et al., Angew. Chem. Int. Ed. 49, 333 (2010)

    Article  CAS  Google Scholar 

  178. R.C. Elgersma, T. Meijneke, R. De Jong, A.J. Brouwer, G. Posthuma, D.T. Rijkers, R.M. Liskamp, Org. Biomol. Chem. 4, 3587 (2006)

    Article  CAS  PubMed  Google Scholar 

  179. R. Maini, L.M. Dedkova, R. Paul, M.M. Madathil, S.R. Chowdhury, S. Chen, S.M. Hecht, J. Am. Chem. Soc. 137, 11206 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  180. L.S. Victorova, V.V. Kotusov, A.V. Azhaev, A.A. Krayevsky, M.K. Kukhanova, B.P. Gottikh, FEBS Lett. 68, 215 (1976)

    Google Scholar 

  181. K.L. Dunbar, D.H. Scharf, A. Litomska, C. Hertweck, Chem. Rev. 117, 5521 (2017)

    Article  CAS  PubMed  Google Scholar 

  182. A. Bondi, J. Phys. Chem. 68, 441 (1964)

    Article  CAS  Google Scholar 

  183. L. Pauling, in The Nature of the Chemical Bond and the Structure of Molecules and Crystals: An Introduction to Modern Structural Chemistry (Cornell University Press, Ithaca, 1960)

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Pennsylvania, 213 South 34th Street, Philadelphia, PA, 19104, USA

    Taylor M. Barrett, Kristen E. Fiore, Chunxiao Liu & E. James Petersson

  2. Department of Applied Chemistry, China Agricultural University, Yuanmingyuan West Road 2, Beijing, 100193, China

    Chunxiao Liu

Authors
  1. Taylor M. Barrett
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kristen E. Fiore
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chunxiao Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. James Petersson
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. James Petersson .

Editor information

Editors and Affiliations

  1. Gifu University, Gifu, Japan

    Toshiaki Murai

Rights and permissions

Reprints and permissions

Copyright information

© 2019 Springer Nature Singapore Pte Ltd.

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Barrett, T.M., Fiore, K.E., Liu, C., James Petersson, E. (2019). Thioamide-Containing Peptides and Proteins. In: Murai, T. (eds) Chemistry of Thioamides. Springer, Singapore. https://doi.org/10.1007/978-981-13-7828-7_8

Download citation

Publish with us

Policies and ethics

Search

Navigation