Subscribe to RSS
DOI: 10.1055/s-0036-1588860
Ynamide: A New Coupling Reagent for Amide and Peptide Synthesis
This work was supported by National Science Foundation of China (21462023) and the Nature Science Foundation of Jiangxi Province (20143ACB20007, 20153BCB23018).Publication History
Received: 21 April 2017
Accepted after revision: 11 May 2017
Publication Date:
29 June 2017 (online)
Abstract
The discovery and application of ynamide coupling reagents is highlighted with a brief summary of the development history of coupling reagents in amide and peptide synthesis. As novel coupling reagents, ynamides are not only effective for simple amide and dipeptide synthesis but also can be used for peptide fragment condensation. More importantly, no racemization was detected during the activation of α-chiral carboxylic acids by employing ynamide coupling reagents.
1 Introduction
2 Carbodiimide Coupling Reagents
3 Uronium/Guanidinium Salt Coupling Reagents
4 Phosphonium Salt Coupling Reagents
5 Ethoxyacetylene as a Coupling Reagent
6 Ynamine Coupling Reagents
7 Ynamide Coupling Reagents
8 Summary and Outlook
-
References
- 1 Pattabiraman VR. Bode JW. Nature (London, U.K.) 2011; 480: 471
- 2 Jursic BS. Zdravkovski Z. Synth. Commun. 1993; 23: 2761
- 3 Sheehan JC. Hess GP. J. Am. Chem. Soc. 1955; 77: 1067
- 4 Gawne G. Kenner GW. Sheppard RC. J. Am. Chem. Soc. 1969; 91: 5669
- 5 Carpino LA. Henklein P. Foxman BM. Abdelmoty I. Costisella B. Wray V. Domke T. El-Faham A. Mügge C. J. Org. Chem. 2001; 66: 5245
- 6 El-Faham A. Albericio F. Chem. Rev. 2011; 111: 6557
- 7a Kamiński ZJ. Kolesińska B. Kolesińska J. Sabatino G. Chelli M. Rovero P. Błaszczyk M. Główka ML. Papini AM. J. Am. Chem. Soc. 2005; 127: 16912
- 7b Li H. Jiang X. Ye Y.-H. Fan C. Romoff T. Goodman M. Org. Lett. 1999; 1: 91
- 7c Tian J. Gao W.-C. Zhou D.-M. Zhang C. Org. Lett. 2012; 14: 3020
- 7d Orliac A. Gomez Pardo D. Bombrun A. Cossy J. Org. Lett. 2013; 15: 902
- 7e Subirós-Funosas R. Prohens R. Barbas R. El-Faham A. Albericio F. Chem. Eur. J. 2009; 15: 9394
- 8 Hu L. Xu S. Zhao Z. Yang Y. Peng Z. Yang M. Wang C. Zhao J. J. Am. Chem. Soc. 2016; 138: 13135
- 9 Anderson GW. Callahan FM. J. Am. Chem. Soc. 1958; 80: 2902
- 10 König W. Geiger R. Chem. Ber. 1970; 103: 2024
- 11 Carpino LA. Philbin M. J. Org. Chem. 1999; 64: 4315
- 12 König W. Geiger R. Chem. Ber. 1970; 103: 788
- 13 Spetzler C. Meldal J. Felding M. Vedso J. Begtrup PM. J. Chem. Soc., Perkin Trans. 1 1998; 1727
- 14a Benoiton NL. Chen FM. F. J. Chem. Soc., Chem. Commun. 1981; 543
- 14b Izdebski J. Kunce D. J. Pept. Sci. 1997; 3: 141
- 14c Carpino LA. El-Faham A. Tetrahedron 1999; 55: 6813
- 15 Dourtoglou V. Ziegler J.-C. Gross B. Tetrahedron Lett. 1978; 19: 1269
- 16a Hood CA. Fuentes G. Patel H. Page K. Menakuru M. Park JH. J. Pept. Sci. 2008; 14: 97
- 16b Abdelmoty I. Albericio F. Carpino LA. Foxman BM. Kates SA. Lett. Pept. Sci. 1994; 1: 57
- 16c El-Faham A. Org. Prep. Proced. Int. 1998; 30: 477
- 16d Li P. Xu J.-C. Tetrahedron 2000; 56: 4437
- 16e del Fresno M. El-Faham A. Carpino LA. Royo M. Albericio F. Org. Lett. 2000; 2: 3539
- 16f Carpino LA. El-Faham A. Albericio F. J. Org. Chem. 1995; 60: 3561
- 16g Knorr R. Trzeciak A. Bannwarth W. Gillessen D. Tetrahedron Lett. 1989; 30: 1927
- 16h Dourtoglou V. Gross B. Lambropoulou V. Zioudrou C. Synthesis 1984; 572
- 17 Carpino LA. Imazumi H. El-Faham A. Ferrer FJ. Zhang C. Lee Y. Foxman BM. Henklein P. Hanay C. Mügge C. Wenschuh H. Klose J. Beyermann M. Bienert M. Angew. Chem. Int. Ed. 2002; 41: 441
- 18a El-Faham A. Albericio F. Org. Lett. 2007; 9: 4475
- 18b El-Faham A. Albericio F. J. Org. Chem. 2008; 73: 2731
- 19 Kraatz U. Tetrahedron Lett. 1973; 14: 1219
- 20a Coste J. Frerot E. Jouin P. J. Org. Chem. 1994; 59: 2437
- 20b Jou G. González I. Albericio F. Lloyd-Williams P. Giralt E. J. Org. Chem. 1997; 62: 354
- 21 Coste J. Le-Nguyen D. Castro B. Tetrahedron Lett. 1990; 31: 205
- 22 Arens JF. Recl. Trav. Chim. Pays-Bas 1955; 74: 769
- 23a Ruppin C. Dixneuf PH. Lecolier S. Tetrahedron Lett. 1988; 29: 5365
- 23b Bruneau C. Neveux M. Kabouche Z. Ruppin C. Dixneuf PH. Synlett 1991; 755
- 23c Kabouche Z. Bruneau C. Dixneuf PH. Tetrahedron Lett. 1991; 32: 5359
- 23d Ishino Y. Nishiguchi I. Nakao S. Hirashima T. Chem. Lett. 1981; 10: 641
- 23e Kita Y. Maeda H. Omori K. Okuno T. Tamura Y. J. Chem. Soc., Perkin Trans. 1 1993; 2999
- 23f Krause T. Baader S. Erb B. Gooßen LJ. Nat. Commun. 2016; 7: 11732
- 24 Buijle R. Viehe HG. Angew. Chem., Int. Ed. Engl. 1964; 3: 582
- 25a van Mourik AS. Harryvan E. Arens JF. Recl. Trav. Chim. Pays-Bas 1965; 84: 1344
- 25b Weygand F. König W. Buyle R. Viehe HG. Chem. Ber. 1965; 98: 3632
- 26 Gais HJ. Hafner K. Neuenschwander M. Helv. Chim. Acta 1969; 52: 2641
- 27 Gais H.-J. Angew. Chem., Int. Ed. Engl. 1978; 17: 597
- 28a Neuenschwander M. Fahrni H.-P. Lienhard U. Helv. Chim. Acta 1978; 61: 2437
- 28b Neuenschwander M. Lienhard U. Fahrni H.-P. Hurni B. Helv. Chim. Acta 1978; 61: 2428
- 28c Neuenschwander M. Helv. Chim. Acta 2015; 98: 881
- 29 Gais H.-J. Lied T. Angew. Chem., Int. Ed. Engl. 1978; 17: 267
- 30a Wang T. Yuan L. Zhao Z. Shao A. Gao M. Huang Y. Xiong F. Zhang H. Zhao J. Green Chem. 2015; 17: 2741
- 30b Zhao Z. Wang T. Yuan L. Hu X. Xiong F. Zhao J. Adv. Synth. Catal. 2015; 357: 2566
- 30c Zhao Z. Wang T. Yuan L. Jia X. Zhao J. RSC Adv. 2015; 5: 75386
- 31a DeKorver KA. Li H. Lohse AG. Hayashi R. Lu Z. Zhang Y. Hsung RP. Chem. Rev. 2010; 110: 5064
- 31b Evano G. Coste A. Jouvin K. Angew. Chem. Int. Ed. 2010; 49: 2840
- 31c Gwilherm E. Nicolas B. Guillaume C. Alexis CS. D. C. Wafa G. Céline G. Jérémy H. Nicolas H. Kévin J. Ganesan K. Anouar L. Morgan L. Agnès M.-M. Benoît M. Bastien M. Antoine N. Cédric T. Sébastien T. Jianjun W. Maxence Z. Chunyang Z. Chem. Lett. 2016; 45: 574
- 32 Smith DL. Goundry WR. F. Lam HW. Chem. Commun. 2012; 48: 1505
- 33 Xu S. Liu J. Hu D. Bi X. Green Chem. 2015; 17: 184