Microwave-assisted solid-phase peptide synthesis at 60°C: Alternative conditions with low enantiomerization

Journal of Peptide Science

Volumn 15, Issue 12, 2009, Pages 808-817

  Loffredo, Carina ^a   Assunção, Nilson A ^a   Gerhardt, Juergen ^b   Miranda, M Terêsa Machini ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b CAT GmbH and Co Chromatographie und Analysentechnik KG   (Germany)

Author keywords

Conventional heating; High temperature; Microwave technology; Peptide analysis; Peptide isomers; Racemization

Indexed keywords

CHOLECYSTOKININ; GLYCYLCYSTYLPHENYLAMINE; HISTIDINE; METHIONINE; PEPTIDE; SERINE; TOLUENE; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; ARTICLE; CAPILLARY ELECTROPHORESIS; CHIRAL CHROMATOGRAPHY; COUPLING FACTOR; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOMER; HEATING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH TEMPERATURE; HYDROLYSIS; MICROWAVE COOKING; MICROWAVE RADIATION; PEPTIDE ANALYSIS; PRIORITY JOURNAL; PROTEIN CLEAVAGE; PROTEIN SYNTHESIS; RACEMIZATION; SOLID PHASE SYNTHESIS;

AMINO ACID SEQUENCE; AMINO ACIDS; CHOLECYSTOKININ; CHROMATOGRAPHY, LIQUID; ELECTROPHORESIS, CAPILLARY; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HEATING; MICROWAVES; MOLECULAR SEQUENCE DATA; PEPTIDES; STEREOISOMERISM; TANDEM MASS SPECTROMETRY; TEMPERATURE;

EID: 73349124783     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1178     Document Type: Article

References (40)

1. Bodansky M. Racemization. In Peptides - A Practical Textbook. Bodansky M (ed.). Springer: Berlin, 1993; 117-128.
2. Merrifield RB. Solid phase synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 1963; 85: 2149-2154. DOI: 10.1021/ja00897a025.
3. Atherton E, Sheppard RC. Solid phase peptide synthesis: A Practical Approach, IRL Press: Oxford, 1989; 216.
4. Jung G, Beck-Sickinger AG. Multiple peptide synthesis methods and their applications. New synthetic methods. Angew. Chem. Int. Ed. Engl. 1992; 31: 367-383. DOI: 10.1002/anie.199203673.
5. Eichler J, Appel JR, Blondelle SE, Dooley CT, Doerner B, Ostresh JM, Perez-Paya E, Pinilla C, Houghten RA. Peptide, peptidomimetic, and organic synthetic combinatorial libraries. Med. Res. Rev. 1995; 15: 481-496. DOI: 10.1002/med.2610150603.
6. Borgia JA, Fields GB. Chemical synthesis of proteins. Trends. Biotechnol. 2000; 18: 243-251.
7. Benoiton NL. Chemistry of Peptide Synthesis. CRC Press, Taylor & Francis Group: Boca Raton, 2005; 93-124.
8. Lloyd-Williams P, Albericio F, Giralt E. Chemical Approaches to the Synthesis of Peptides and Proteins. CRC: Boca Raton, FL, 1997; 278.
9. Rabinovich AK, Rivier JE. In Peptides: Chemistry, Structure and Biology (Proc. 13th. Am. Pept. Symp.) Hodges RS, Smith JA (eds.). Escom Science Publishers BV: Leiden, The Netherlands; 1994; 71-73.
10. Varanda LM, Miranda MTM. Solid-phase peptide synthesis at elevated temperature: a search for an optimized synthesis condition of unsulfated cholecystokinin-12. J. Pept. Res. 1997; 50: 102-108.
11. Rivier JE, Miranda MTM. Solid-phase peptide synthesis at elevated temperature. In Synthesis of Peptides and Peptidomimetics. Goodman M, Felix A, Moroder L, Toniolo C (eds.). Stuttgart: Thieme: 2002; E22a, 806-813.
12. Souza MP, Tavares MFM, Miranda MTM. Racemization in stepwise solid-phase peptide synthesis at elevated temperatures. Tetrahedron 2004; 60: 4671-4681. DOI: 10.1016/j.tet.2004.03.070.
13. Remuzgo C, Andrade GFS, Temperini MLA, Miranda MTM. Synthesis at 60 °C of a novel difficult sequence. Biopolymers 2009; 92: 65-75. DOI: 10.1002/bip.21110.
14. Kappe CO. Speeding Up Solid-phase Chemistry by Microwave Irradiation. A New Tool for High-Throughput Synthesis, vol. 33, American Laboratory: Shelton, CT, 2001; 13-19.
15. Brandt M, Gammeltoft S, Jensen KJ. Microwave heating for solidphase peptide synthesis: general evaluation and application to 15-mer phosphopeptides. Int. J. Pept. Res. Ther. 2006; 12: 349-357. DOI: 10.1007/s10989-006-9038-z.
16. Palasek S, Cox ZJ, Collins JM. Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis. J. Pept. Sci. 2007; 13: 143-148. DOI: 10.1002/psc.804.
17. Bacsa B, Desai B, Gábar D, Kappe CO. Rapid solid-phase peptide synthesis using thermal and controlled microwave irradiation. J. Pept. Sci. 2006; 12: 633-638. DOI: 10.1002/psc.771.
18. Bacsa B, Horváti K, Bosze S, Andreae F, Kappe CO. Solid-phase synthesis of difficult peptide sequences at elevated temperatures: a critical comparison of microwave and conventional heating technologies. J. Org. Chem. 2008; 73: 7532-7542. DOI: 10.1021/jo8013897.
19. Loffredo C, Assunção NA, Miranda MTM. Further studies on solid-phase peptide synthesis at high temperature. In Peptides for Youth (Proc. 20th. Am. Pept. Symp.). Del Valle S, Escher E, Lubell WD (eds.). Advances in Experimental Medicine and Biology, 611, Springer: New York, 2009; 165-166.
20. Han Y, Albericio F, Barany G. Occurrence and minimization of cysteine racemization during stepwise solid-phase peptide synthesis. J. Org. Chem. 1997; 62: 4307-4312. DOI: 10.1021/jo9622744.
21. Li Y, Luo L, Thomas DY, Kang CY. Control of expression, glycosylation, and secretion of HIV-1 gp120 by homologous and heterologous signal sequences. Virology 1994; 204: 266-278. DOI: 10.1006/viro.1994.1531.
22. Miranda MTM, Liddle RA, Rivier JE. Synthesis of human CCK26-33 and CCK-33 related analogues on 2,4-DMBHA and TMBH. J. Med. Chem. 1993A; 36: 1681-1688. DOI: 10.1021/jm00064a001.
23. Reeve Jr JR, Wu SV, Keire DA, Faull K, Chew P, Solomon TE, Green GM, Coskun T. Differential bile-pancreatic secretory effects of CCK-58 and CCK-8. Am. J. Physiol. Gastrointest. Liver Physiol. 2004; 286: 395-402. DOI: 10.1152/ajpgi.00020.2003.
24. Fogaça AC, Silva PL, Miranda MTM, Bianchi AG, Miranda A, Ribolla PEM, Daffre S. Antimicrobial activity of a bovine hemoglobin fragment in the tick Boophilus microplus. J. Biol. Chem. 1999; 274: 25330-25334. DOI: 10.1074/jbc.274.36.25330.
25. 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: 203-208. DOI: 10.1007/s10989-006-9066-8.
26. Kaiser E, Colescott RL, Bossinger CD, Cook PI. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970; 34: 595-598.
27. Smillie LB, Nattriss M. Amino acid analyses of proteins and peptides: an overview. In High Performace Liquid Chromatography of Peptides and Proteins ± Separation, Analysis and Conformation. Mant CT, Hodges RS (eds.). CRC Press: Boca Raton, 1991; 847-863.
28. Stewart JM, Young JD. Solid Phase Peptide Synthesis, 2nd edn, Pierce Chemical Company: Rockford, IL, 1984; 176.
29. Grossman PD, Colburn JC. Capillary Electrophoresis Theory and Practice. Academic Press: San Diego, 1992; 352.
30. Kemp D. The Peptides: Analysis, Synthesis, Biology. Gross E, Meienhoefer J. (eds.). Academic Press: New York, 1979; 315.
31. Gerhardt J, Nicholson GJ. In Peptides: Chemistry, Structure and Biology (Proc. 13th. Am. Pept. Symp.). Hodges RS, Smith JA (eds.). Escom Science Publishers BV: Leiden, The Netherlands, 1994; 241-243.
32. Collins JM, Leadbeater NE.Microwave energy: a versatile tool for the biosciences. Org. Biomol. Chem. 2007; 5: 1141-1150.
33. Houghten RA, Li CH. Reduction of sulfoxides in peptides and proteins. Anal. Biochem. 1979; 98: 36-46. DOI: 10.1016/0003-2697(79)90702-4.
34. Huang H, Rabenstein DL. A cleavage cocktail for methionine-containing peptides. J. Pept. Res. 1999; 53: 548-553.
35. Guo L, Funakoshi S, Fujii N, Yajima H. Studies on peptides. CLXV.1,2 Combination of a new amide-precursor reagent and trimethylsilyl bromide deprotection for the 9-fluorenylmethyloxycarbonyl-based solid-phase synthesis of chicken antral peptide. Chem. Pharm. Bull. 1988; 36: 4989-4992.
36. Pennington MW, Byrnes ME. Evaluation of TiCl4-mediated reduction of methionine sulfoxide in peptides with oxidizable or reducible residues. Pept. Res. 1995; 8: 39-43.
37. Beck W, Jung G. Convenient reduction of S-oxides in synthetic peptides, lipopeptides and peptide libraries. Lett. Pept. Sci. 1994; 1: 31-37. DOI: 10.1007/BF00132760.
38. Rapp W, Bayer E. Peptides 1992 (Proc.22ndEur. Pept. Symp.). Epton R (ed.). Escom Science Publishers BV: Leiden, The Netherlands, 1992; 259-266.
39. Hayes BL. Microwave Synthesis: Chemistry at the Speed of Light. CEM Publishing:Matthews, NC, 2002; 29-75.
40. Maertens C, Detrembleur C, Dubois P, Jerome R, Boutton C, Persoons A, Kogej T, Breâdas JL. Structure-second-order polarizability relationship in chromophores incorporation a spacer: A joint experimental and theoretical study. Chem. Eur. J. 1999; 5: 369-380. DOI: 10.1002/(SICI)1521- 3765(19990104)5 : 1 <369::AIDCHEM369> 3.0.CO;2-5.