The evolution of peptide synthesis: From early days to small molecular machines

Current Bioactive Compounds

Volumn 9, Issue 3, 2013, Pages 184-202

  Mollica, Adriano ^a   Pinnen, Francesco ^a   Stefanucci, Azzurra ^b   Costante, Roberto ^a,c  

^a UNIVERSITY OF CHIETI   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

Fmoc chemistry; LPPS; Molecular machine; Native chemical ligation; SPPS

Indexed keywords

MACROGOL; RESIN; SYNTHETIC PEPTIDE;

AFFINITY CHROMATOGRAPHY; ATMOSPHERIC PRESSURE; CAPILLARY ELECTROPHORESIS; CAPILLARY ISOELECTRIC FOCUSING; COUNTER CURRENT CHROMATOGRAPHY; ELECTROSPRAY; FLUORESCENCE; GEL PERMEATION CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBIC INTERACTION CHROMATOGRAPHY; ION EXCHANGE CHROMATOGRAPHY; LIGHT SCATTERING; MICROFILTRATION; NANOFILTRATION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN ISOLATION; PROTEIN PURIFICATION; REVERSE OSMOSIS; REVIEW; SOLID PHASE SYNTHESIS; ULTRAFILTRATION; ULTRAVIOLET RADIATION;

EID: 84893092108     PISSN: 15734072     EISSN: 18756646     Source Type: Journal    
DOI: 10.2174/157340720903140119151919     Document Type: Review

References (85)

1. du Vigneaud, V.; Ressler, C.; Swan, C.J.M.; Carleton, Roberts, C.W.; Katsoyannis, P.G.; Gordon, S. The Synthesis of an Octapeptide amide with the Hormonal Activity of Oxytocin. J. Am. Chem. Soc. 1953, 75, 4879-4880.
2. Merrifield, R.B. Solid Phase Peptide Synthesis. I. The Synthesis of a Tetrapeptide. J. Am. Chem. Soc. 1963, 85, 2149-2154.
3. Horvath, C.G.; Lipsky, S.R. Column design in high-pressure liquid chromatography. J. Chromatogr. Sci. 1969, 7, 109-116.
4. Locatelli, M.; Governatori, L.; Carlucci, G.; Genovese, S.; Mollica, A.; Epifano, F. Recent application of analytical methods to phase I and phase II drugs development: a review. Biomed. Chromatogr. 2012, 26, 283-300.
5. Hruby, V.J. Peptide science: Exploring the use of chemical principles and interdisciplinary collaboration for understanding life processes. J. Med. Chem. 2003, 46, 4215-4231.
6. Carpino, L.A.; Han, G.Y. 9-Fluorenylmethoxycarbonyl aminoprotecting group. J. Org. Chem. 1972, 37, 3404-3409.
7. Fields, G.B.; Noble, R.L. Solid phase peptide synthesis utilizing 9fluorenylmethoxycarbonyl amino acids. Int. J. Pept. Protein Res. 1990, 35, 161-214.
8. Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiu, G.; Sotiriu, P.; Wenqing, Y.; Schfer, W. Applicability of substituted triphenylmethyl resins for the synthesis of protected peptide fragments. Tetrahedron Lett. 1989, 30, 3943-3946.
9. Fischer, E.; Fourneau, E. Ueber einige Derivate des Glykokolls, Ber. Dtsch. Chem. Ges. 1901, 34, 2868-2879.
10. Curtius, T. Ueber einige neue der Hippursäure analog constituirte, synthetisch dargestellte Amidosäuren. J. prakt. Chem. 1882, 26, 145-208.
11. Curtius, T. Verkettung von Amidosäuren. J. prak. Chem. 1904, 70, 57-108.
12. Fischer, E. Synthese von Polypeptiden. IX. Chloride der Aminosäuren und ihrer Acylderivate. Ber. Dtsch. Chem. Ges. 1905, 38, 605-619.
13. Harington, C.R.; Mead, T.H. Synthesis of glutathione. Biochem. J. 1935, 29, 1602-1611.
14. Sifferd, R.H.; du Vigneaud, V. A new synthesis of carnosine, with some observations on the splitting of the benzyl group from carbobenzoxy derivatives and from benzylthio ethers. J. Biol. Chem. 1935, 108, 753-761.
15. Sheehan, J.C.; Hess, G.P. A new method of forming peptide bonds. J. Am. Chem. Soc. 1955, 77, 1067-1068.
16. Khorana, H. G. The use of dicyclohexylcarbodiimide in the synthesis of peptides. Chem. Ind. (London, United Kingdom), 1955, 33, 1087-1088.
17. Goodman, M.; McGahren, W.J. Mechanistic studies of peptide oxazolone racemization. Tetrahedron, 1967, 23, 2031-2050.
18. König, W.; Geiger, R. N-Hydroxyverbindungen als Katalysatoren für die Aminolyse aktivierter Ester. Chem. Ber. 1973, 106, 3626-3635.
19. Subiros-Funosas, R.; El-Faham, A.; Albericio, F. PyOxP and PyOxB: the Oxyma-based novel family of phosphonium salts. Org. Biomol. Chem. 2010, 8, 3665-3673.
20. Hetnarski, B.; Merrifield, R.B. Kinetics of coupling reactions in solid-phase peptide synthesis. Peptides: Chemistry and Biology, Proceedings of the 10th American Peptide Symposium, 1988, 220-222.
21. Miranda, L.P.; Alewood, P.F. Accelerated chemical synthesis of peptides and small proteins. Proceedings of the National Academy of Sciences of the United States of America, 1999, 96, 1181-1186.
22. Applied Biosystems. FastMoc Chemistry: HBTU Activation Chemistry in Peptide Synthesis on Model 430A, 1990.
23. Fields, C.G.; Lloyd, D.H.; Macdonald, R.L.; Otteson, K.M.; Noble, R.L. HBTU activation for automated Fmoc solid-phase peptide synthesis. Pept. Res. 1991, 4, 95-101.
24. Schnolzer, M.; Alewood, P.; Jones, A.; Alewood, D.; Kent, S.B.H. In situ neutralization in Boc-chemistry solid phase peptide synthesis rapid, high yield assembly of difficult sequences. Int. J. Pept. Res. Ther. 2007, 13, 31-44.
25. Carpino, L.A. 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive. J. Am. Chem. Soc. 1993, 115, 4397-4398.
26. Alewood, P.; Alewood, D.; Miranda, L.; Love, S.; Meutermans, W.; Wilson, D. Rapid in situ neutralization protocols for Boc and Fmoc solid-phase chemistries. Methods Enzymol. 1997, 289, 14-29.
27. Marder, O.; Shvo, Y.; Albericio, F. HCTU and TCTU. New coupling reagents: development and industrial aspects. Chim. Oggi, 2002, 20, 37-41.
28. Sabatino, G.; Mulinacci, B.; Alcaro, M.C.; Chelli, M.; Rovero, P.; Papini, A.M. Assessment of new 6-Cl-HOBt based coupling reagents for peptide synthesis. Part 1: Coupling efficiency study. Lett. Pept. Sci. 2003, 9, 119-123.
29. Sabatino, G.; Alcaro M.C.; Pozo-Carrero, M.D.L.; Chelli, M.; Rovero, P.; Papini, A.M. Assessment of 6Cl-HOBt-based coupling reagents in solid-phase cyclopeptide synthesis. Peptides-American Symposium, 2004, 18, 49-50.
30. Peptide International. 2007-2008, Catalog, 66-67.
31. Brunetti, L.; Ferrante, C.; Orlando, G.; Recinella, L.; Leone, S.; Chiavaroli, A.; Di Nisio, C.; Shohreh, R.; Manippa, F.; Ricciuti, A.; Mollica, A.; Vacca, M. Orexigenic effects of endomorphin-2 (EM2) related to decreased CRH gene expression and increased dopamine and norepinephrine activity in the hypothalamus. Peptides, 2013, 48, 83-88.
32. Mollica, A.; Costante, R.; Stefanucci, A.; Pinnen, F.; Luisi, G.; Pieretti, S.; Borsodi, A.; Bojnik, E.; Benyhe, S. Hybrid peptides endomorphin-2/DAMGO: Design, synthesis and biological evaluation. Eur. J. Med. Chem. 2013, 68, 167-177.
33. Giordano, C.; Sansone, A.; Masi, A.; Lucente, G.; Punzi, P.; Mollica, A.; Pinnen, F.; Feliciani, F.; Cacciatore, I.; Davis, P.; Lai, J.; Ma, S.W.; Porreca, F.; Hruby, V. Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2. Eur. J. Med. Chem. 2010, 45, 4594-4600.
34. Torino, D.; Mollica, A.; Pinnen, F.; Lucente, G.; Feliciani, F. Davis, P.; Lai, J.; Ma, S.W.; Porreca, F.; Hruby, V.J. Bioorg. Med. Chem. Lett., 2009, 19, 4115-4118.
35. Mollica, A.; Costante, R.; Stefanucci, A.; Pinnen, F.; Lucente, G.; Fidanza, S.; Pieretti, S. Antinociceptive profile of potent opioid peptide AM94, a fluorinated analogue of biphalin with nonhydrazine linker. J. Pept. Sci. 2013, 19, 233-239.
36. 3-peptides. J. Med. Chem. 2013, 56, 3419-3423.
37. Mollica, A.; Pinnen, F.; Feliciani, F.; Stefanucci, A.; Lucente, G. Davis, P.; Porreca, F.; Ma, S.W.; Lai, J.; Hruby, V.J. New potent biphalin analogues containing p-fluoro-L-phenylalanine at the 4,4' positions and non-hydrazine linkers. Amino acids, 2011, 40, 1503-1511.
38. Mollica, A.; Feliciani, F.; Stefanucci, A.; Costante, R.; Lucente, G.; Pinnen, F.; Notaristefano, D.; Spisani, S. Synthesis and biological evaluation of new active For-Met-Leu-Phe-OMe analogues containing para-substituted Phe residues. J. Pept. Sci. 2012, 18, 418-426.
39. Torino, D.; Mollica, A.; Pinnen, F.; Feliciani, F.; Spisani, S.; Lucente, G. Bioorg. Med. Chem., 2009, 17, 251-259.
40. Mollica, A.; Paradisi, M.P.; Varani, K.; Spisani, S.; Lucente, G. Chemotactic peptides: fMLF-OMe analogues incorporating proline-methionine chimeras as N-terminal residue. Bioorg. Med. Chem. 2006, 14, 2253-2265.
41. Mollica, A.; Davis, P.; Ma, S.W.; Porreca, F.; Lai, J.; Hruby, V.J. Synthesis and biological activity of the first cyclic biphalin analogues. Bioorg. Med. Chem. Lett. 2006, 16, 367-372.
42. Mollica, A.; Pinnen, F.; Stefanucci, A.; Feliciani, F.; Campestre, C.; Mannina, L.; Sobolev, A.P.; Lucente, G.; Davis, P.; Lai, J.; Ma, S.W.; Porreca, F.; Hruby, V.J. The cis-4-amino-L-proline residue as a scaffold for the synthesis of cyclic and linear endomorphin-2 analogues. J. Med. Chem. 2012, 55, 3027-3035.
43. Mollica, A.; Pinnen, F.; Stefanucci, A.; Mannina, L.; Sobolev, A.P.; Lucente, G.; Davis, P.; Lai, J.; Ma, S.W.; Porreca, F.; Hruby, V.J. Cis-4-amino-l-proline residue as a scaffold for the synthesis of cyclic and linear endomorphin-2 analogues: Part 2. J. Med. Chem. 2012, 55, 8477-8482.
44. Mollica, A.; Guardiani, G.; Davis, P.; Ma, S.W.; Porreca, F.; Lai, J.; Mannina, L.; Sobolev, A.P.; Hruby, V.J. Synthesis of stable and potent/ opioid peptides: Analogues of H-Tyr-c[D-Cys-Gly-Phe-D-Cys]-OH by ring-closing metathesis. J. Med. Chem. 2007, 50, 3138-3142.
45. Okada, Y.; Fukumizu, A.; Takahashi, M.; Shimizu, Y.; Tsuda, Y.; Yokoi, T.; Bryant, S.D.; Lazarus, L.H. Synthesis of stereoisomeric analogues of endomorphin-2, H-Tyr-Pro-Phe-Phe-NH2, and examination of their opioid receptor binding activities and solution conformation. Biochem. Biophys. Res. Commun. 2000, 276, 7-11.
46. Sivanandaiah, K.M.; Gurusiddappa, S.; Gowda, D.C.; Babu, V.V.S. Improved solid phase synthesis of luteinizing hormone releasing hormone analogues using 9-fluorenylmethyloxycarbonyl amino acid active esters and catalytic transfer hydrogenation with minimal side-chain protection and their biological activities. J. Biosci. 1989, 14, 311-317.
47. Hood, C.A.; Fuentes, G.; Patel, H.; Page, K.; Menakuru, M.; Park, J.H. Fast conventional Fmoc solid-phase peptide synthesis with HCTU. J. Pept. Sci. 2008, 14, 97-101.
48. Kent, S.B.H. New aspects of solid phase peptide synthesis. In Biomed. Polym. Goldberg, E.P., Nakajima, A., Eds; Academic Press: Waltham, MA, 1980, 213-242.
49. 13C solid-state NMR: Evidence of excessive misfolding for Alzheimer's. J. Am. Chem. Soc. 2012, 134, 2848-2851.
50. Sampson, W.R.; Patsiouras, H.; Ede, N.J. J. Pept. Sci. 1999, 5, 403-409.
51. Simmonds, R.G. Use of the Hmb backbone-protecting group in the synthesis of difficult sequences. Int. J. Pept. Prot. Res. 1996, 47, 36-41.
52. Zeng, W.; Regamey, P.O.; Rose, K.; Wang, Y.; Bayer, E. Use of Fmoc-N-(2-hydroxy-4-methoxybenzyl)amino acids in peptide synthesis. J. Pept. Res. 1997, 49, 273-279.
53. Carpino, L.A.; Nasr, K.; Abdel-Maksoud, A.A.; El-Faham, A.; Ionescu, D.; Henklein, P.; Wenschuh, H.; Beyermann, M.; Krause, E.; Bienert, M. The dicyclopropylmethyl (Dcpm) peptide backbone protectant. Org. Lett. 2009, 11, 3718-3721.
54. Thakkar, A.; Trinh, T.B.; Pei, D. Global analysis of peptide cyclization efficiency. ACS Comb. Sci. 2013, 15, 120-129.
55. Malesevic, M.; Strijowski, U.; Ba chle, D.; Sewaldm, N. An improved method for the solution cyclization of peptides under pseudohigh dilution conditions. J. Biotechnol. 2004, 12, 73-77.
56. Kami ski, Z.J. Orthogonal protecting groups for N-amino and C-terminal carboxyl functions in solid-phase peptide synthesis. Biopolymers-Peptide Science Section, 2000, 55, 123-139.
57. Van den Nest, W.; Albericio, F. The choice of the solid support. In optimization of solid-phase combinatorial synthesis. Yan, B.; Czarnik, A.W. eds. Marcel Dekker, New York (NY, USA), 2001, 91-107.
58. Vaino, A.R., Janda, K.D. Solid-phase organic synthesis: a critical understanding of the resin. J. Comb. Chem. 2000, 2, 579-596.
59. Hudson, D. Matrix assisted synthetic transformations: a mosaic of diverse contributions. I. The pattern emerges. J. Comb. Chem. 1999, 1, 333-360.
60. Meldal, M. Properties of solid supports. Methods Enzymol. 1997, 289, 83-104.
61. Li, W.; Xiao, X.; Czarnik A.W. Kinetic Comparison of Amide Formation on Various Cross-Linked Polystyrene Resins. J. Comb. Chem. 1999, 1, 127-128.
62. Kamysz, W.; Okrój, M.; empicka, E.; Ossowski, T.; ukasiak, J. Fast and efficient purification of synthetic peptides by solid-phase extraction, Acta Chromatogr. 2004, 14, 180-186.
63. Rivier, J.; McClintock, R. Reversed phase high performance liquid chromatography of insulins from different species. J. Chromatogr. 1983, 268, 112-119.
64. M. Kunitani and D. Johnson, Model of Protein Conformation in the Reversed-Phase Separation of Interleukin-2 Muteins, J. Chromatogr. 1986, 371, 313-333.
65. Wang, W.; de Mejia, E.G. A new frontier in soy bioactive peptides that may prevent age-related diseases. Compr. Rev. Food Sci. Food Saf. 2005, 4, 63-78.
66. Megias, C.; Pedroche, J.; Yust, M.M.; Giron-Calle, J.; Alaiz, M.; Milan, F.; Vioque, J. Affinity purification of copper chelating peptides from sunflower protein hydrolysates. J. Agric. Food Chem. 2007, 55, 6509-6514.
67. Megias, C.; Pedroche, J.; Yust, M.M.; Alaiz, M.; Giron-Calle, J.; Millan, F.; Vioque, J. J. Agric. Food Chem. 2006, 54, 4641-4645.
68. Megias, C.; Pedroche, J.; Yust, M.M.; Alaiz, M.; Giron-Calle, J.; Millan, F.; Vioque, J. Affinity purification of angiotensin converting enzyme inhibitory peptides using immobilized ACE, J. Agric. Food Chem. 2006, 54, 7120-7124.
69. Pouliot, Y.; Gauthier, S.F.; Groleau, P.E. Nutraceutical Proteins and Peptides in Health and Disease, Y. Mine & F. Shahidi (Eds), Taylor & Francis Group, Boca Raton, FL, 2006, 639-658.
70. Srajer Gajdosika, M.; Clifton, J.; Josic, D. Sample displacement chromatography as a method for purification of proteins and peptides from complex mixtures, J. Chromatogr. A, 2012, 1239, 1-9.
71. Shahidi, F.; Zhong, Y. Bioactive peptides. J. AOAC Int. 2008, 91.
72. Ahmed, F. E. The role of capillary electrophoresis-mass spectrometry to proteome analysis and biomarker discovery. J. Chromatogr. B, 2009, 877, 1963-1981.
73. Haselberg, R.; de Jong, G.J.; Somsen, G.W. Capillary electrophoresis-mass spectrometry using noncovalently coated capillaries for the analysis of biopharmaceuticals. Anal. Chim. Acta, 2010, 678, 128-134.
74. Wojcik, R.; Dada, O.O.; Sadilek, M.; Dovichi, N.J. Simplified capillary electrophoresis nanospray sheath-flow interface for high efficiency and sensitive peptide analysis Rapid Commun. Mass Spectrom. 2010, 24, 2554-2560.
75. Tomás, R.; Koval, M.; Foret, F. Coupling of hydrodynamically closed large bore capillary isotachophoresis with electrospray mass spectrometry. J. Chromatogr. A, 2010, 1217, 4144-4149.
76. Martin, G.B.; Mansion, F.; Servais, A.C.; Debrus, B.; Rozet, E.; Hubert, P.; Crommen, J.; Fillet, M. CE-MS method development for peptides analysis, especially hepcidin, an iron metabolism marker. Electrophoresis, 2009, 30, 2624-2631.
77. Pe, O.; Preisler, J. Off-line coupling of microcolumn separations to desorption mass spectrometry. J. Chromatogr. A, 2010, 1217, 3966-3977.
78. Kasicka, V. Recent developments in CE and CEC of peptides (2009-2011). Electrophoresis, 2012, 33, 48-73.
79. van den Broeka, I.; Wilfried M.A.; van Dongena, W.D. Bioanalytical LC-MS/MS of protein-based biopharmaceuticals, J. Chromatogr. B, 2013, 929, 161-179.
80. Crawford, E.D.; Eisenberger, M.A.; McLeod, D.G.; Spaulding, J.T.; Benson, R.; Dorr, F.A.; Blumenstein, B.A.; Davis, M.A.; Goodman, P.J. A controlled trial of leuprolide with and without flutamide in prostatic carcinoma. N. Engl. J. Med. 1989, 321, 419-424.
81. Lewandowski, B.; De Bo, G.; Ward, J.W.; Papmeyer, M.; Kuschel, S.; Aldegunde, M.J.; Gramlich, P.M.E.; Heckmann, D.; Goldup, S.M.; D'Souza, D.M.; Fernandes, A.E.; Leigh, D.A. Sequence specific peptide synthesis by an artificial small-molecule machine. Science, 2013, 339, 189-193.
82. Yonath, A. Hibernating Bears, Antibiotics, and the Evolving Ribosome. Angew. Chem. Int. Ed. 2010, 49, 4340-4354.
83. Finking, R.; Marahiel, M.A. Biosynthesis of Nonribosomal Peptides. Annu. Rev. Microbiol. 2004, 58, 453-488.
84. Hackenberger, C.P.R.; Schwarzer, D. Chemoselective Ligation and Modification Strategies for Peptides and Proteins. Angew. Chem. Int. Ed. 2008, 47, 10030-10074.
85. Stefanucci, A.; Pinnen, F.; Feliciani, F.; Cacciatore, I.; Lucente, G.; Mollica, A. Conformationally Constrained Histidines in the Design of Peptidomimetics: Strategies for the Space Control. Int. J. Mol. Sci. 2011, 12, 2853-2890.