Controlled solid phase peptide bond formation using N-carboxyanhydrides and PEG resins in water

ACS Sustainable Chemistry and Engineering

Volumn 1, Issue 6, 2013, Pages 566-569

  De Marco, Rossella ^a   Tolomelli, Alessandra ^a   Greco, Arianna ^a   Gentilucci, Luca ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Aqueous; Microwave irradiation; N carboxyanhydride; PEG resin; Peptide amide; Solid phase peptide synthesis; Unprotected amino acids

Indexed keywords

AQUEOUS; BIOLOGICALLY ACTIVE PEPTIDES; CONTROLLED CONDITIONS; ENVIRONMENTAL SUSTAINABILITY; N-CARBOXYANHYDRIDES; PEPTIDE AMIDES; SOLID PHASE PEPTIDE SYNTHESIS; SOLID-PHASE PEPTIDES;

AMIDES; AMINO ACIDS; MICROWAVE IRRADIATION; RESINS;

PEPTIDES;

EID: 84884211651     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc400058r     Document Type: Article

References (38)

1. Hruby, V. J. Designing peptide receptor agonists and antagonists Nat. Rev. Drug Discovery 2002, 1 (11) 847-858
2. Gentilucci, L.; Tolomelli, A.; Squassabia, F. Peptides and peptidomimetics in medicine, surgery and biotechnology Curr. Med. Chem. 2006, 13 (20) 2449-2466
3. Zhang, L.; Falla, T. J. Cosmeceuticals and peptides Clin. Dermatol. 2009, 27 (5) 485-494
4. Stevenson, C. L. Advances in peptide pharmaceuticals Curr. Pharm. Biotechnol. 2009, 10 (1) 122-137
5. Scott, E.; Peter, F.; Sanders, J. Biomass in the manufacture of industrial products-the use of proteins and amino acids Appl. Microbiol. Biotechnol. 2007, 75 (4) 751-762
6. Williams, P. J. le B.; Laurens, L. M. L. Microalgae as biodiesel & biomass feedstocks: Review & analysis of the biochemistry, energetics & economics Energy Environ. Sci. 2010, 3, 554-590
7. Lammens, T. M.; Franssen, M. C. R.; Scott, E. L.; Sanders, J. P. M. Availability of protein-derived amino acids as feedstock for the production of bio-based chemicals Biomass Bioenergy 2012, 44, 168-181
8. Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C., Eds.; Synthesis of Peptides and Peptidomimetics; Thieme: Stuttgart, 2002; Vol. E22.
9. Anastas, P. T.; Williamson, T. C., Eds.; Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes; Oxford University Press: New York, 1999.
10. Dunn, P. J.; Wells, A. S.; Williams, M. T., Eds.; Green Chemistry in the Pharmaceutical industry; Wiley-VCH Verlag GmbH & Co.: Weinheim, 2010.
11. Silpi, D.; Abha, S.; Torok, M. Steps toward green peptide synthesis Curr. Org. Synth. 2011, 8 (2) 262-280
12. Declerck, V.; Nun, P.; Martinez, J.; Lamaty, L. Solvent-free synthesis of peptides Angew. Chem., Int. Ed. 2009, 48 (49) 9318-9321
13. Štrukil, V.; Bartolec, B.; Portada, T.; Crossed D signilović, I.; Halaszc, I.; Margetić, D. One-pot mechanosynthesis of aromatic amides and dipeptides from carboxylic acids and amines Chem. Commun. 2012, 48, 12100-12102
14. Bonnamour, J.; Métro, T.-X.; Martinez, J.; Lamaty, F. Environmentally benign peptide synthesis using liquid-assisted ballmilling: Application to the synthesis of Leu-enkephalin Green Chem. 2013, 10.1039/C3GC40302E
15. Hojo, K.; Ichikawa, H.; Onishi, M.; Fukumori, Y.; Kawasaki, K. Peptide synthesis 'in water' by a solution-phase method using water-dispersible nanoparticle Boc-amino acid J. Pept. Sci. 2011, 17 (7) 487-492 and references herein.
16. Athanassios, S.; Albericio, F.; Grøtli, M. Solid-phase peptide synthesis in water using microwave-assisted heating Org. Lett. 2009, 11 (20) 4488-4491
17. Hojo, K.; Maeda, M.; Tanakamaru, N.; Mochida, K.; Kawasaki, K. Solid phase peptide synthesis in water VI: Evaluation of water-soluble coupling reagents for solid phase peptide synthesis in aqueous media Protein Pept. Lett. 2006, 13 (2) 189-192 and references herein.
18. Schellenberger, V.; Jakubke, H. D. Protease-catalyzed kinetically controlled peptide synthesis Angew. Chem., Int. Ed. Engl. 1991, 30 (11) 1437-1449
19. Wong, C. H. Enzymatic catalysts in organic synthesis Science 1989, 244 (4909) 1145-1152
20. Góngora-Benítez, M.; Basso, A.; Bruckdorfer, T.; Royo, M.; Tulla-Puche, J.; Albericio, F. Eco-friendly combination of the immobilized PGA enzyme and the S-Phacm protecting group for the synthesis of Cys-containing peptides Chem.-Eur. J. 2012, 18 (50) 16166-16176
21. Katritzky, A. R.; Zhang, Y.; Singh, S. K. Efficient conversion of carboxylic acids into N-acylbenzotriazoles Synthesis 2003, 48 (18) 2795-2798
22. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. Synthesis of proteins by native chemical ligation Science 1994, 266 (5186) 776-779
23. Johnson, E. C. B.; Durek, T.; Kent, S. B. H. Total chemical synthesis, folding, and assay of a small protein on a water-compatible solid support Angew. Chem., Int. Ed. 2006, 45 (20) 3283-3287
24. Denkewalter, R. G.; Schwam, H.; Strachan, R. G.; Beesley, T. E.; veber, D. F.; Schoenwaldt, E. F.; Barkemeyer, H.; Paleveda, W. J., Jr.; Jacob, T. A.; Hirschmann, R. The controlled synthesis of peptides in aqueous medium. I. The use of α-amino acid N -carboxyanhydrides J. Am. Chem. Soc. 1966, 83 (11) 3163-3164
25. Montalbetti, C. A. G. N.; Falque, V. Amide bond formation and peptide coupling Tetrahedron 2005, 61 (5) 10827-10852
26. Spina, R.; Colacino, E.; Gabriele, B.; Salerno, G.; Martinez, J.; Lamaty, F. Synthesis of pyrrolin-4-ones by Pt-catalyzed cycloisomerization in PEG under microwaves J. Org. Chem. 2013, 78 (6) 2698-2702
27. Zadina, J. E.; Hackler, L.; Lin-Jun, G.; Kastin, A. J. A potent and selective endogenous agonist for the μ-opiate receptor Nature 1997, 386 (6624) 499-502
28. Keresztes, A.; Borics, A.; Tóth, G. Recent advances in endomorphin engineering Chem. Med. Chem. 2010, 5 (8) 1176-1196
29. Gentilucci, L. Addressing the Interactions between Opioid Ligands and Their Receptors. Classic and Nonclassic Cases. In Neuropeptides in Neuroprotection and Neuroregeneration; Nyberg, F., Ed.; CRC Press: Boca Raton, FL, 2012; pp 229-252.
30. De Marco, R.; Tolomelli, A.; Spampinato, S.; Bedini, A.; Gentilucci, L. Opioid activity profiles of oversimplified peptides lacking in the protonable N -terminus J. Med. Chem. 2012, 55 (22) 10292-10296
31. Trotzki, R.; Nüchter, M.; Ondruschka, B. Microwave assisted phosgenation-alcoholysis using triphosgene Green Chem. 2003, 5 (3) 285-290
32. Fuse, S.; Tanabe, N.; Takahashi, T. Continuous in situ generation and reaction of phosgene in a microflow system Chem. Commun. 2011, 47 (44) 12661-12663
33. Wilder, R.; Mobashery, S. The use of triphosgene in preparation of N -carboxy α-amino acid anhydrides J. Org. Chem. 1992, 57 (9) 2755-2756
34. Gulin, P. O.; Rabanal, F.; Giralt, E. Efficient preparation of proline N-carboxyanhydride using polymer-supported bases Org. Lett. 2006, 8 (23) 5385-5388
35. Kramer, J. R.; Deming, T. J. General method for purification of α-amino acid- N -carboxyanhydrides using flash chromatography Biomacromolecules 2010, 11 (12) 3668-3672
36. Palacios, P.; Bussat, P.; Bichon, D. Synthesis of a thiol-terminated poly(L-glutamic acid) by polymerization of N-carboxyanhydrides on solid supports Angew. Chem., Int. Ed. 1991, 193 (1) 77-88
37. García-Ramos, Y.; Paradís-Bas, M.; Tulla-Puche, J.; Albericio, F. ChemMatrix® for complex peptides and combinatorial chemistry J. Pept. Sci. 2010, 16 (12) 675-678
38. Webster, R.; Elliott, V.; Park, B. K.; Walker, D.; Hankin, M.; Taupin, P. PEG and PEG Conjugates toxicity: Towards an Understanding of the Toxicity of PEG and Its Relevance to PEGylated Biologicals. In PEGylated Protein Drugs: Basic Science and Clinical Applications. Milestones in Drug Therapy; Veronese, F. M., Ed.; Birkhäuser: Basel, Switzerland, 2009.