Synthesis 2019; 51(09): 1913-1922
DOI: 10.1055/s-0037-1612418
short review
© Georg Thieme Verlag Stuttgart · New York

Advanced Approaches to Post-Assembly Modification of Peptides by Transition-Metal-Catalyzed Reactions

Sambasivarao Kotha*
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400 076, India   Email: srk@chem.iitb.ac.in
,
Milind Meshram
,
Nageswara Rao Panguluri
› Author Affiliations
We thank the Council of Scientific and Industrial Research (CSIR), New Delhi [02(0272)/16/EMRII] and the Department of Science and Technology (DST), New Delhi (EMR/2015/002053, SR/S2/JCB-33/2010) for financial support. S.K. thanks the Department of Science and Technology (DST) for the award of a J. C. Bose fellowship (SR/S2/JCB-33/2010) and Praj Industries, Pune for the Pramod Chaudhari Chair Professorship (Green Chemistry).
Further Information

Publication History

Received: 11 December 2018

Accepted after revision: 13 February 2019

Publication Date:
25 March 2019 (eFirst)

Abstract

We have summarized diverse synthetic approaches for the modification of peptides by employing transition-metal-catalyzed reactions. These methods can deliver unusual peptides suitable for peptidomimetics. To this end, several popular reactions such as Diels–Alder, 1,3-dipolar cycloaddition, [2+2+2] cyclotrimerization, metathesis, Suzuki­–Miyaura cross-coupling, and Negishi coupling have been used to assemble modified peptides by post-assembly chemical modification strategies.

1 Introduction

2 Synthesis of a Cyclic α-Amino Acid Derivative via a Ring-Closing Metathesis Protocol

3 Peptide Modification Using a Ring-Closing Metathesis Strategy

4 Peptide Modification via a [2+2+2] Cyclotrimerization Reaction

5 Peptide Modification by Using [2+2+2] Cyclotrimerization and Suzuki Coupling

6 Peptide Modification via a Suzuki–Miyaura Cross-Coupling

7 Peptide Modification via Cross-Enyne Metathesis and a Diels–Alder­ Reaction as Key Steps

8 Peptide Modification via 1,3-Dipolar Cycloaddition Reactions

9 Modified Peptides via Negishi Coupling

10 A Modified Dipeptide via Ethyl Isocyanoacetate

11 Conclusions

 
  • References

    • 1a Gante J. Angew. Chem., Int. Ed. Engl. 1994; 33: 1699
    • 1b Liskamp RM. J. Angew. Chem., Int. Ed. Engl. 1994; 33: 633
    • 1c Schiller PW. Conformational Analysis of Enkephalin and Confirmation–Activity Relationships. In The Peptides: Analysis, Synthesis, Biology, Vol. 6. Udenfriend S, Meienhofer J. Academic Press; Orlando: 1984. Chap. 7, 219-268
    • 2a Liskamp RM. J. Recl. Trav. Chim. Pays-Bas 1994; 113: 1
    • 2b Gibson SE, Guillo N, Tozer MJ. Tetrahedron 1999; 55: 585
    • 3a Kotha S. Acc. Chem. Res. 2003; 36: 342
    • 3b Balaram P. Curr. Opin. Struct. Biol. 1992; 2: 845
    • 3c Casabona D, Cativiela C. Synthesis 2006; 2440
    • 3d Kazmaier U, Deska J. Curr. Org. Chem. 2008; 12: 355
    • 3e Kazmaier U, Maier S, Zumpe FL. Synlett 2000; 1523
    • 4a Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 36: 3437
    • 4b Miyaura N, Suzuki A. J. Chem. Soc., Chem. Commun. 1979; 866
    • 4c Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
    • 4d Kotha S, Lahiri K, Kashinath D. Tetrahedron 2002; 58: 9633
    • 4e Kotha S, Lahiri K. Eur. J. Org. Chem. 2007; 1221
    • 4f Kotha S, Mandal K. Chem. Asian. J. 2009; 4: 354
    • 4g Kotha S, Meshram M, Chakkapalli C. Beilstein J. Org. Chem. 2018; 14: 2468
    • 5a Kotha S, Lahiri K. Synlett 2007; 2767
    • 5b Kotha S, Meshram M, Tiwari A. Chem. Soc. Rev. 2009; 38: 2065
    • 5c Kotha S, Krishna NG, Halder S, Misra S. Org. Biomol. Chem. 2011; 9: 5597
    • 5d Kotha S, Dipak MK. Tetrahedron 2012; 68: 397
    • 5e Kotha S, Meshram M, Khedkar P, Banerjee S, Deodhar D. Beilstein J. Org. Chem. 2015; 11: 1833
    • 5f Kotha S, Meshram M, Dommaraju Y. Chem. Rec. 2018; 18: 1613
    • 5g Kotha S, Meshram M. Chem. Asian J. 2018; 13: 1758
  • 6 Räder AF. B, Weinmüller M, Reichart F, Schumacher-Klinger A, Merzbach S, Gilon C, Hoffman A, Kessler H. Angew. Chem. Int. Ed. 2018; 57: 14414
    • 7a Willemse T, Schepens W, van Vlijmen HW. T, Maes BU. W, Ballet S. Catalysts 2017; 7: 74
    • 7b Willemse T, Van Imp K, Goss RJ. M, Van Vlijmen HW. T, Schepens W, Maes BU. W, Ballet S. ChemCatChem 2015; 7: 2055
  • 8 Gao Z, Gouverneur V, Davis BG. J. Am. Chem. Soc. 2013; 135: 13612
  • 9 Nam HY, Seo J. Biopolymers: Pept. Sci. 2016; 106: 82
  • 10 Webster AM, Cobb SL. Tetrahedron Lett. 2017; 58: 1010
  • 11 Lin YA, Chalker JM, Davis BG. ChemBioChem 2009; 10: 959
  • 12 Kotha S, Meshram M. J. Organomet. Chem. 2018; 874: 13
  • 13 Kotha S, Sreenivasachary N. Bioorg. Med. Chem. Lett. 1998; 8: 257
    • 14a Kotha S, Brahmachary E. Bioorg. Med. Chem. Lett. 1997; 7: 2719
    • 14b Kotha S, Brahmachary E. J. Org. Chem. 2000; 65: 1359
    • 14c Kotha S, Halder S. Synlett 2010; 337
    • 14d Kotha S, Goyal D, Chavan AS. J. Org. Chem. 2013; 78: 12288
  • 15 Kotha S, Sreenivasachary N, Mohanraja K, Durani S. Bioorg. Med. Chem. Lett. 2001; 11: 1421
    • 16a Kotha S, Mohanraja K, Durani S. Chem. Commun. 2000; 1909
    • 16b Kotha S, Brachmachary E. Bioorg. Med. Chem. 2002; 10: 2291
  • 17 Sreevani G. Ph.D. Thesis. IIT-Bombay; India: 2018
  • 18 Kotha S, Lahiri K. Bioorg. Med. Chem. Lett. 2001; 11: 2887
  • 19 Kotha S, Lahiri K. Biopolymers 2003; 69: 517
  • 20 Yoburn JC, Van Vranken DL. Org. Lett. 2003; 5: 2817
  • 21 Espuña G, Arsequell G, Valencia G, Barluenga J, Alvarez-Gutiérrez JM, Ballesteros A, González JM. Angew. Chem. Int. Ed. 2004; 43: 325
  • 22 Vilaró M, Arsequell G, Valencia G, Ballesteros A, Barluenga J. Org. Lett. 2008; 10: 3243
  • 23 Limbach M, Löweneck M, Schreiber JV, Frackenpohl J, Seebach D, Billich A. Helv. Chim. Acta 2006; 89: 1427
  • 24 Meyer F.-M, Liras S, Guzman-Perez A, Perreault C, Bian J, James K. Org. Lett. 2010; 12: 3870
  • 25 Kotha S, Goyal D, Thota N, Srinivas V. Eur. J. Org. Chem. 2012; 1843
  • 26 Kotha S, Goyal D, Banerjee S, Datta A. Analyst 2012; 137: 2871
  • 27 Kotha S, Goyal D, Bitra A, Thota N, Kruger G, Anand R. RSC Adv. 2013; 3: 24447
  • 28 King AO, Okukado N, Negishi EI. J. Chem. Soc., Chem. Commun. 1977; 683
  • 29 Kotha S, Todeti S. Beilstein. J. Org. Chem. 2019; 15: 371
  • 30 Kotha S, Behera M. Indian J. Chem. 2004; 43B: 922
    • 31a Kinsinger S, Kazmaier U. Org. Lett. 2018; 20: 7726
    • 31b Barbie P, Kazmaier U. Org. Lett. 2016; 18: 204
    • 31c Lee HG, Lautrette G, Pentelute BL, Buchwald SL. Angew. Chem. Int. Ed. 2017; 56: 3177
    • 31d Hopkins BA, Smith GF. Sciammetta N. Org. Lett. 2016; 18: 4072
    • 31e Ohata J, Minus MB, Abernathy ME, Ball ZT. J. Am. Chem. Soc. 2016; 138: 7472
    • 31f Lawson KV, Rose TE, Harran PG. Proc. Natl. Acad. Sci. U.S.A. 2013; 110: E3753