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Synthesis 2020; 52(21): 3189-3210
DOI: 10.1055/s-0040-1706296
DOI: 10.1055/s-0040-1706296
special topic
Recent Advances in Amide Bond Formation
OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis
We are grateful to the American Chemical Society (ACS) Green Chemistry Institute (GCI) (Pharmaceutical Roundtable Ignition Grant) for funding S.R.M. In addition, the work in laboratory of the authors was funded in part by the following: the South African Agency for Science and Technology Advancement, The National Research Foundation (NRF) (Blue Sky’s Research Programme, Grant No. 120386) and the University of KwaZulu-Natal (South Africa); the Ministerio de Ciencia e Innovación (Spanish Ministry of Science, Innovation) (RTI2018-093831-B-100), the Departament d’Innovació, Universitats i Empresa, Generalitat de Catalunya (2017 SGR 1439) and the Ministerio de Economía y Competitividad; and the International Scientific Partnership Program ISPP at King Saud University, Saudi Arabia, Riyadh (ISPP# 0061).
Abstract
OxymaPure [ethyl 2-cyano-2-(hydroxyimino)acetate] is an exceptional reagent with which to suppress racemization and enhance coupling efficiency during amide bond formation. The tremendous popularity of OxymaPure has led to the development of several Oxyma-based reagents. OxymaPure and its derived reagents are widely used in solid- and solution-phase peptide chemistry. This review summarizes the recent developments and applications of OxymaPure and Oxyma-based reagents in peptide chemistry, in particular in solution-phase chemistry. Moreover, the side reaction associated with OxymaPure is also discussed.
1 Introduction
2 Oxyma-Based Coupling Reagents
2.1 Aminium/Uronium Salts of OxymaPure
2.2 Phosphonium Salts of OxymaPure
2.3 Oxyma-Based Phosphates
2.4 Sulfonate Esters of OxymaPure
2.5 Benzoate Esters of OxymaPure
2.6 Carbonates of OxymaPure Derivatives
3 OxymaPure Derivatives
4 Other Oxime-Based Additives and Coupling Reagents
5 Side Reactions Using OxymaPure Derivatives
6 Conclusion
7 List of Abbreviations
Publication History
Received: 15 July 2020
Accepted after revision: 27 August 2020
Article published online:
30 September 2020
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References
- 1 Scarso A, Pellizzaro L, De Lucchi O, Linden A, Fabris F. Angew. Chem. Int. Ed. 2007; 46: 4972
- 2 Collins J, Xiao Z, Müllner M, Connal LA. Polym. Chem. 2016; 7: 3812
- 3 Bednarczyk-Cwynar B, Zaprutko L. Phytochem. Rev. 2015; 14: 203
- 4 Bergström MA, Andersson SI, Broo K, Luthman K, Karlberg A.-T. J. Med. Chem. 2008; 51: 2541
- 5 Li J, Hu Y, Zhang D, Liu Q, Dong Y, Liu H. Adv. Synth. Catal. 2017; 359: 710
- 6 Nikitjuka A, Jirgensons A. Chem. Heterocycl. Compd. 2014; 49: 1544
- 7 Sahyoun T, Arrault A, Schneider R. Molecules 2019; 24: 2470
- 8 Bednarczyk-Cwynar B. Nat. Prod. Commun. 2011; 6: 1813
- 9 Zhou X.-T, Yuan Q.-L, Ji H.-B. Tetrahedron Lett. 2010; 51: 613
- 10 Ramón RS, Bosson J, Díez-González S, Marion N, Nolan SP. J. Org. Chem. 2010; 75: 1197
- 11 Lemercier BC, Pierce JG. J. Org. Chem. 2014; 79: 2321
- 12 Ding R, Liu Y, Han M, Jiao W, Li J, Tian H, Sun B. J. Org. Chem. 2018; 83: 12939
- 13 Li Y.-T, Liao B.-S, Chen H.-P, Liu S.-T. Synthesis 2011; 2639
- 14 Santosh Kumar SC, Vijendra Kumar N, Srinivas P, Bettadaiah BK. Synthesis 2014; 46: 1847
- 15 Kumar R, Chowdhury B. Ind. Eng. Chem. Res. 2014; 53: 16587
- 16 Bruton EA, Brammer L, Pigge FC, Aakeröy CB, Leinen DS. New J. Chem. 2003; 27: 1084
- 17 Aakeröy CB, Sinha AS, Epa KN, Chopade PD, Smith MM, Desper J. Cryst. Growth Des. 2013; 13: 2687
- 18 Subirós-Funosas R, Prohens R, Barbas R, El-Faham A, Albericio F. Chem. Eur. J. 2009; 15: 9394
- 19 Subiros-Funosas R, Khattab SN, Nieto-Rodriguez L, El-Faham A, Albericio F. Aldrichimica Acta 2013; 46: 21
- 20 Isidro-Llobet A, Kenworthy MN, Mukherjee S, Kopach ME, Wegner K, Gallou F, Smith AG, Roschangar F. J. Org. Chem. 2019; 84: 4615
- 21 Reszka P, Methling K, Lalk M, Xiao Z, Weisz K, Bednarski PJ. Tetrahedron: Asymmetry 2008; 19: 49
- 22 Abdelmoty I, Albericio F, Carpino LA, Foxman BM, Kates SA. Lett. Pept. Sci. 1994; 1: 57
- 23 Marder O, Shvo Y, Albericio F. Chim. Oggi 2002; 20: 37
- 24 Hood CA, Fuentes G, Patel H, Page K, Menakuru M, Park JH. J. Pept. Sci. 2008; 14: 97
- 25 Speicher A, Klaus T, Eicher T. J. Prakt. Chem./Chem. Ztg. 1998; 340: 581
- 26 Sureshbabu VV, Lalithamba HS, Narendra N, Hemantha HP. Org. Biomol. Chem. 2010; 8: 835
- 27 McKnelly KJ, Sokol W, Nowick JS. J. Org. Chem. 2020; 85: 1764
- 28 Wehrstedt KD, Wandrey PA, Heitkamp D. J. Hazard. Mater. 2005; 126: 1
- 29 El-Faham A, Subirós Funosas R, Prohens R, Albericio F. Chem. Eur. J. 2009; 15: 9404
- 30 El-Faham A, Albericio F. J. Pept. Sci. 2010; 16: 6
- 31 Hjelmgaard T, Faure S, Staerk D, Taillefumier C, Nielsen J. Org. Biomol. Chem. 2011; 9: 6832
- 32 Hjørringgaard CU, Brust A, Alewood PF. J. Pept. Sci. 2012; 18: 199
- 33 Samarasimhareddy M, Hosahalli PH, Kuppanna A, Vommina VS. Protein Pept. Lett. 2012; 19: 406
- 34 Subiros-Funosas R, Acosta GA, El-Faham A, Albericio F. Tetrahedron Lett. 2009; 50: 6200
- 35 Tyrrell E, Brawn P, Carew M, Greenwood I. Tetrahedron Lett. 2011; 52: 369
- 36 El-Faham A, Funosas RS, Prohens R, Albericio F. Chem. Eur. J. 2009; 15: 9404
- 37 Subirós-Funosas R, Nieto-Rodriguez L, Jensen KJ, Albericio F. J. Pept. Sci. 2013; 19: 408
- 38 Kumar A, Jad YE, de la Torre BG, El-Faham A, Albericio F. J. Pept. Sci. 2017; 23: 763
- 39 Gabriel CM, Keener M, Gallou F, Lipshutz BH. Org. Lett. 2015; 17: 3968
- 40 Cortes-Clerget M, Berthon J.-Y, Krolikiewicz-Renimel I, Chaisemartin L, Lipshutz BH. Green Chem. 2017; 19: 4263
- 41 Twibanire J.-dA. K, Grindley TB. Org. Lett. 2011; 13: 2988
- 42 Panguluri NR, Basavaprabhu, Sureshbabu VV. Int. J. Pept. Res. Ther. 2014; 20: 377
- 43 Junker A, Schepmann D, Yamaguchi J, Itami K, Faust A, Kopka K, Wagner S, Wünsch B. Org. Biomol. Chem. 2014; 12: 177
- 44 Miao Y, Djedaïni-Pilard F, Bonnet V. Beilstein J. Org. Chem. 2014; 10: 2654
- 45 Manabe S, Ito Y. Beilstein J. Org. Chem. 2016; 12: 328
- 46 Withey JM, Bajic A. J. Chem. Educ. 2015; 92: 175
- 47 Scholz MS, Wingen LM. Inorg. Chem. 2017; 56: 5510
- 48 Poock C, Kalesse M. Org. Lett. 2017; 19: 4536
- 49 Albericio F, Bofill JM, El-Faham A, Kates SA. J. Org. Chem. 1998; 63: 9678
- 50 Story SC, Aldrich JV. Int. J. Pept. Protein Res. 1994; 43: 292
- 51 Albericio F, Cases M, Alsina J, Triolo SA, Carpino LA, Kates SA. Tetrahedron Lett. 1997; 38: 4853
- 52 Subirós-Funosas R, El-Faham A, Albericio F. Org. Biomol. Chem. 2010; 8: 3665
- 53 Dettin M, Silvestri D, Danesin R, Cretaio E, Picariello G, Casarin E, Sonato A, Romanato F, Morpurgo M. Molecules 2012; 17: 11026
- 54 El-Faham A, Khattab SN, Subirós-Funosas R, Albericio F. J. Pept. Sci. 2014; 20: 1
- 55 Mitachi K, Kurosu YE, Hazlett BT, Kurosu M. J. Pept. Sci. 2016; 22: 186
- 56 Khattab SN. Chem. Pharm. Bull. 2010; 58: 501
- 57 Palakurthy NB, Dev D, Rana S, Nadimpally KC, Mandal B. Eur. J. Org. Chem. 2013; 2627
- 58 Dev D, Palakurthy NB, Kumar N, Mandal B. Tetrahedron Lett. 2013; 54: 4397
- 59 Dev D, Palakurthy NB, Thalluri K, Chandra J, Mandal B. J. Org. Chem. 2014; 79: 5420
- 60 Manne SR, Chandra J, Giri RS, Kalita T, Mandal B. ChemistrySelect 2018; 3: 992
- 61 Dev D, Chandra J, Palakurthy NB, Thalluri K, Kalita T, Mandal B. Asian J. Org. Chem. 2016; 5: 663
- 62 Crescenzi O, Tomaselli S, Guerrini R, Salvadori S, D’Ursi AM, Temussi PA, Picone D. Eur. J. Biochem. 2002; 269: 5642
- 63 Thalluri K, Manne SR, Dev D, Mandal B. J. Org. Chem. 2014; 79: 3765
- 64 Chandra J, Manne SR, Mondal S, Mandal B. ACS Omega 2018; 3: 6120
- 65 Burugupalli S, Shah S, van der Peet PL, Arora S, White JM, Williams SJ. Org. Biomol. Chem. 2016; 14: 97
- 66 Thalluri K, Nadimpally KC, Chakravarty MP, Paul A, Mandal B. Adv. Synth. Catal. 2013; 355: 448
- 67 Manne SR, Thalluri K, Giri RS, Paul A, Mandal B. Tetrahedron Lett. 2015; 56: 6108
- 68 Marks PA. Oncogene 2007; 26: 1351
- 69 Grant S, Easley C, Kirkpatrick P. Nat. Rev. Drug Discovery 2007; 6: 21
- 70 Salmi-Smail C, Fabre A, Dequiedt F, Restouin A, Castellano R, Garbit S, Roche P, Morelli X, Brunel JM, Collette Y. J. Med. Chem. 2010; 53: 3038
- 71 Manne SR, Thalluri K, Giri RS, Chandra J, Mandal B. Adv. Synth. Catal. 2017; 359: 168
- 72 Khattab SN, Subirós-Funosas R, El-Faham A, Albericio F. Eur. J. Org. Chem. 2010; 3275
- 73 Carpino LA. Acc. Chem. Res. 1987; 20: 401
- 74 Carpino LA, Han GY. J. Org. Chem. 1972; 37: 3404
- 75 Lozanov V, Petrov S, Mitev V. J. Chromatogr. A 2004; 1025: 201
- 76 Paquet A. Can. J. Biochem. 1982; 60: 976
- 77 Tessier M, Albericio F, Pedroso E, Grandas A, Eritja R, Giralt E, Granier C, van Rietschoten J. Int. J. Pept. Protein Res. 1983; 22: 125
- 78 Sigler GF, Fuller WD, Chaturvedi NC, Goodman M, Verlander M. Biopolymers 1983; 22: 2157
- 79 Hlebowicz E, Andersen AJ, Andersson L, Moss BA. J. Pept. Res. 2005; 65: 90
- 80 Kumar A, Sharma A, Haimov E, El-Faham A, de la Torre BG, Albericio F. Org. Process Res. Dev. 2017; 21: 1533
- 81 Masumi I. Bull. Chem. Soc. Jpn. 1973; 46: 2219
- 82 Spengler J, Fernandez-Llamazares A.-I, Albericio F. ACS Comb. Sci. 2013; 15: 229
- 83 Subirós-Funosas R, El-Faham A, Albericio F. Biopolymers 2012; 98: 89
- 84 Cherkupally P, Acosta GA, Nieto-Rodriguez L, Spengler J, Rodriguez H, Khattab SN, El-Faham A, Shamis M, Luxembourg Y, Prohens R, Subiros-Funosas R, Albericio F. Eur. J. Org. Chem. 2013; 6372
- 85 Eylar E, Brostoff S, Hashim G, Caccam J, Burnett P. J. Biol. Chem. 1971; 246: 5770
- 86 Khattab SN, Subirós-Funosas R, El-Faham A, Albericio F. ChemistryOpen 2012; 1: 147
- 87 Wang Q, Wang Y, Kurosu M. Org. Lett. 2012; 14: 3372
- 88 Wang Y, Aleiwi BA, Wang Q, Kurosu M. Org. Lett. 2012; 14: 4910
- 89 Al-Warhi TI, Al-Hazimi H, El-Faham A, Albericio F. Molecules 2010; 15: 9403
- 90 El-Faham A, Al Marhoon Z, Abdel-Megeed A, Khattab SN, Bekhit AA, Albericio F. Bioorg. Med. Chem. Lett. 2015; 25: 70
- 91 Wang D, Li J, Salazar-Alvarez G, McKee LS, Srivastava V, Sellberg JA, Bulone V, Hsieh YS. Y. Green Chem. 2018; 20: 2091
- 92 Abd Alhameed R, Almarhoon Z, Bukhari SI, El-Faham A, de la Torre BG, Albericio F. Molecules 2020; 25: 105
- 93 El-Faham A, Subirós-Funosas R, Albericio F. Eur. J. Org. Chem. 2010; 3641
- 94 Jad YE, Khattab SN, de la Torre BG, Govender T, Kruger HG, El-Faham A, Albericio F. Org. Biomol. Chem. 2014; 12: 8379
- 95 Jad YE, Khattab SN, De la Torre BG, Govender T, Kruger HG, El-Faham A, Albericio F. Molecules 2014; 19: 18953
- 96 Jad YE, de la Torre BG, Govender T, Kruger HG, El-Faham A, Albericio F. Tetrahedron Lett. 2016; 57: 3523
- 97 Kumar A, Jad YE, El-Faham A, de la Torre BG, Albericio F. Lett. Org. Chem. 2019; 16: 30
- 98 Ben Haj Salah K, Inguimbert N. Org. Lett. 2014; 16: 1783
- 99 McFarland AD, Buser JY, Embry MC, Held CB, Kolis SP. Org. Process Res. Dev. 2019; 23: 2099
- 100 Erny M, Lundqvist M, Rasmussen JH, Ludemann-Hombourger O, Bihel F, Pawlas J. Org. Process Res. Dev. 2020; 24: 1341