Advances in automatic, manual and microwave-assisted solid-phase peptide synthesis

Current Opinion in Drug Discovery and Development

Volumn 11, Issue 6, 2008, Pages 762-770

  Sabatino, G ^a   Papini, A M ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Active pharmaceutical ingredients; APIs; Coupling reagents; Cyclopeptides; Microwave assisted solid phase peptide synthesis; MW SPPS; Post translationally modified peptides

Indexed keywords

AMIDE; CYCLOPEPTIDE;

AMINO ACID SEQUENCE; AUTOMATION; CHEMICAL BOND; MOLECULAR MECHANICS; PEPTIDE SYNTHESIS; PROTEIN STRUCTURE; REVIEW; SOLID PHASE SYNTHESIS;

AMINO ACID SEQUENCE; MICROWAVES; PEPTIDES; PEPTIDES, CYCLIC;

EID: 54549091070     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (45)

1. Verlander M: Industrial applications of the solid-phase peptide synthesis - A status report. Int J Pept Res Ther (2007) 13(1-2):75-82. •• Because of the increased manufacture of peptides as APIs, this paper represents an important report on the SPPS method, including a historical overview and a summary of the current status of SPPS development.
2. Merrifield RB, Stewart JM: Automated peptide synthesis. Nature (1965) 207(996):522-523.
3. Albericio F, Kates SA: Coupling methods: Solid phase formation of amide and ester bonds. In: Solid-Phase Synthesis: A Practical Guide. Kates SA, Albericio F (Eds), Marcel Dekker Inc, New York, NY, USA (2000):275-330.
4. Albericio F, Bofill JM, El-Faham A, Kates SA: Use of onium salt-based coupling reagents in peptide synthesis. J Org Chem (1998) 63(26):9678-9683.
5. Yu HM, Chen ST, Wang KT: Enhanced coupling efficiency in solid-phase peptide synthesis by microwave irradiation. J Org Chem (1992) 57(18):4781-4784.
6. Albericio F: Developments in peptide and amide synthesis. Curr Opin Chem Biol (2004) 8(3):211-221. • Provides an overview of the more recent developments in peptide synthesis methodology and describes native chemical ligation and convergent strategies to produce medium to large peptides.
7. Sabatino G, Mulinacci B, Alcaro MC, Chelli M, Rovero P, Papini AM: Assessment of new 6Cl-HOBt based coupling reagents for peptide synthesis. Part 1: Coupling efficiency study. Lett Pept Sci (2002) 9(2/3):119-123.
8. Hood CA, Fuentes G, Patel H, Page K, Menakuru M, Park JH: Fast conventional Fmoc solid-phase peptide synthesis with HCTU. J Pept Sci (2008) 14(1):97-101.
9. Kamiński ZJ, Kolesińska B, Kolesińska J, Sabatino G, Chelli M, Rovero P, Błaszczyk M, Główka ML, Papini AM: N-triazinylammonium tetrafluoroborates. A new generation of efficient coupling reagents useful for peptide synthesis. J Am Chem Soc (2005) 127(48):16912-16920.
10. Jastrza̧bek K, Kolesińska B, Sabatino G, Rizzolo F, Papini AM, Kamiński ZJ: Benzyloxy derivatives of triazine-based coupling reagents designed for an efficient solid phase peptide synthesis on polystyrene resin. Int J Pept Res Ther (2007) 13(1-2):229-236.
11. Kolesińska B, Fra̧czyk J, Sabatino G, Papini AM, Kamiński ZJ: Sulfonates of N-triazinylammonium salts as highly efficient, inexpensive and environmentally friendly coupling reagents for peptide synthesis. Chem Today (2007) 25(1):10-13.
12. Schnölzer M, Alewood P, Jones A, Alewood D, Kent SBH: In situ neutralization in Boc-chemistry solid phase peptide synthesis: Rapid, high yield assembly of difficult sequences. Int J Pept Res Ther (2007) 13(1-2):31-44.
13. α-9- fluorenylmethyloxycarbonyl-solid phase peptide synthesis. Chem Pharm Bull (2007) 55(3):468-470.
14. Jubilut GN, Miranda MT, Tominaga MT, Okada Y, Miranda A, Nakaie CR: Resin selection based on the lability of peptidyl-resin linkage towards HF and TFA steps: Dependence on the C-terminal amino acid and peptide length. Chem Pharm Bull (1999) 47(11):1560-1563.
15. Palasek SA, Cox ZJ, Collins JM: Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis. J Pept Sci (2007) 13(3):143-148. • Peptides containing Cys, His and Asp residues, which are prone to racemization and aspartimide formation, were obtained by an appropriate protocol using an automatic microwave instrument.
16. Fara MA, Dìaz-Mochòn JJ, Bradley M: Microwave-assisted coupling with DIC/HOBt for the synthesis of difficult peptoids and fluorescently labelled peptides - A gentle heat goes a long way. Tetrahedron Lett (2006) 47(6):1011-1014.
17. Coantic S, Subra G, Martinez J: Microwave-assisted solid phase peptide synthesis on high loaded resins. Int J Pept Res Ther (2008) 14(2):143-147. • Demonstrates the importance of maintaining stirring during MW-SPPS with high-loaded resins.
18. Bacsa B, Desai B, Dibó G, Kappe CO: Rapid solid-phase peptide synthesis using thermal and controlled microwave irradiation. J Pept Sci (2007) 12(10):633-638.
19. Katritzky AR, Khashab NM, Yoshioka M, Haase DN, Wilson KR, Johnson JV, Chung A, Haskell-Luevano C: Microwave-assisted solid-phase peptide synthesis utilizing N-Fmoc-protected (α-aminoacyl) benzotriazoles. Chem Biol Drug Des (2007) 70(5):465-468.
20. Brandt M, Gammeltoft S, Jensen KJ: Microwave heating for solid-phase peptide synthesis: General evaluation and application to 15-mer phosphopeptides. Int J Pept Res Ther (2006) 12(4):349-357.
21. Murray JK, Gellman SH: Applications of microwave irradiation to the synthesis of 14-helical β-peptides. Org Lett (2005) 7(8):1517-1520.
22. Rahman SA, El-Kafrawy A, Hattaba A, Anwer MF: Optimization of solid-phase synthesis of difficult peptide sequences via comparison between different improved approaches. Amino Acids (2007) 33(3):531-536.
23. Čemažar M, Craik DJ: Microwave-assisted Boc-solid phase peptide synthesis of cyclic cysteine-rich peptides. J Pept Sci (2007) 14(6):683-689.
24. Alcaro MC, Lolli F, Migliorini P, Chelli M, Rovero P, Papini AM: Peptides as autoimmune diseases antigenic probes: A peptide-based reverse approach to detect biomarkers of autoimmune diseases. Chem Today (2007) 25(3):14-16.
25. Mazzucco S, Nardi E, Chelli M, Ginanneschi M, Rapi G, Papini AM, Vergelli M, Mazzanti B, Massacesi L, Amaducci L: Synthesis of lipopeptides of the immunodominant epitope hMBP(83-99) containing amide or C-C bond linked hydrophobic chains for the study of T cell response. Lett Pept Sci (1999) 6(1):51-59.
26. Paolini I, Nuti F, Pozo-Carrero MC, Barbetti F, Kolesińska B, Kamiński ZJ, Chelli M, Papini AM: A convenient microwave-assisted synthesis of N-glycosyl amino acids. Tetrahedron Lett (2007) 48(16):2901-2904.
27. Lolli F, Mulinacci B, Carotenuto A, Bonetti B, Sabatino G, Mazzanti B, D'Ursi AM, Novellino E, Pazzagli M, Lovato L, Alcaro MC et al: An N-glucosylated peptide detecting disease-specific autoantibodies, biomarkers of multiple sclerosis. Proc Natl Acad Sci USA (2005) 102(29):10273-10278.
28. Rizzolo F, Sabatino G, Chelli M, Rovero P, Papini AM: A convenient microwave-enhanced solid-phase synthesis of difficult peptide sequences: Case study of gramicidin A and CSF114(Glc). Int J Pept Res Ther (2007) 13(1-2):203-208.
29. Nagaike F, Onuma Y, Kanazawa C, Hojo H, Ueki A, Nakahara Y, Nakahara Y: Efficient microwave-assisted tandem N- to S-acyl transfer and thioester exchange for the preparation of a glycosylated peptide thiester. Org Lett (2006) 8(20):4465- 4468.
30. 1] gramicidin A. Proc Natl Acad Sci USA (1988) 85(5):1384-1388.
31. Carotenuto A, D'Addona D, Rivalta E, Chelli M, Papini AM, Rovero P, Ginanneschi M: Synthesis of a dicarba-analog of octreotide keeping the type II′ β-turn of the pharmacophore in water solution. Lett Org Chem (2005) 2(3):274-279.
32. 5-selective somatostatin dicarba-analogues: Synthesis and conformation-affinity relationships. J Med Chem (2008) 51(3):512-520.
33. Saxon E, Bertozzi CR: Cell surface engineering by a modified Staudinger reaction. Science (2000) 287(5460):2007-2010.
34. Kolb HC, Finn MG, Sharpless KB: Click chemistry: Diverse chemical function from a few good reactions. Angew Chem Int Ed (2001) 40(11):2004-2021.
35. Agard NJ, Prescher JA, Bertozzi CR: A strain-promoted [3+2]-azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J Am Chem Soc (2004) 126(46):15046-15047.
36. Huisgen R: 1,3-Dipolar Cycloaddition Chemistry. Padwa A (Ed), John Wiley & Sons Ltd, NY, USA (1984):1-176.
37. Kolb HC, Sharpless KB: The growing impact of click chemistry on drug discovery. Drug Discov Today (2003) 8(24):1128-1137.
38. Dondoni A, Giovannini PP, Massi A: Assembling heterocycle-tethered C-glycosyl and α-amino acid residues via 1,3-dipolar cycloaddition reactions. Org Lett (2004) 6(17):2929-2932.
39. Deiters A, Cropp TA, Mukherji M, Chin JW, Anderson JC, Schultz PG: Adding amino acids with novel reactivity to the genetic code of Saccharomyces cerevisiae. J Am Chem Soc (2003) 125(39):11782-11783.
40. Kuijpers BH, Groothuys S, Keereweer AR, Quaedflieg PJ, Blaauw RH, Van Delft FL, Rutjes FP: Expedient synthesis of triazole-linked glycosyl amino acids and peptides. Org Lett (2004) 6(18):3123-3126.
41. Tornøe CW, Christensen C, Meldal M: Peptidotriazoles on solid-phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem (2002) 67(9):3057-3064.
42. Zhang Y-H, Gao Z-X, Zhong C-L, Zhou H-B, Chen L, Wu W-M, Peng X-J, Yao Z-J: An inexpensive fluorescent labeling protocol for bioactive natural products utilizing Cu(I)-catalyzed Huisgen reaction. Tetrahedron (2007) 63(29):6813-6821.
43. Cantel S, Isaad Ale C, Scrima M, Levy JJ, DiMarchi RD, Rovero P, Halperin JA, D'Ursi AM, Papini AM, Chorev M: Synthesis and conformational analysis of a cyclic peptide obtained via i to i+4 intramolecular side-chain to side-chain azide-alkyne 1,3-dipolar cycloaddition. J Org Chem (2008) 73(15):5663-5674.
44. ITALVELLUTI SPA (Kamiński ZJ, Papini AM, Kolesińska B, Kolesińska J, Jastrza̧bek K, Sabatino G, Bianchini R): Process for the preparation of N-triazinylammonium salts. WO-2007051496 (2007).
45. CEM CORP (Collins JM): Microwave enhanced n-Fmoc deprotection in peptide synthesis. EP-01818339 (2007).