Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis

Journal of Peptide Science

Volumn 13, Issue 3, 2007, Pages 143-148

  Palasek, Stacey A ^a   Cox, Zachary J ^a   Collins, Jonathan M ^a  

^a CEM Corporation   (United States)

Author keywords

Aspartimide formation; Fmoc solid phase peptide synthesis; Microwave; Racemization

Indexed keywords

AMINE; AMINO ACID DERIVATIVE; ASPARTIC ACID DERIVATIVE; ASPARTIMIDE; COLLIDINE; CYSTEINE; ESTER; HISTIDINE; PIPERAZINE; PIPERIDINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DEPROTECTION REACTION; INTERMETHOD COMPARISON; LOW TEMPERATURE PROCEDURES; MICROWAVE RADIATION; PRIORITY JOURNAL; PROCESS OPTIMIZATION; PROTEIN BINDING; PROTEIN CONTENT; PROTEIN DETERMINATION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; RACEMIZATION; SOLID PHASE SYNTHESIS;

AMINO ACID SEQUENCE; AMINO ACIDS; ASPARTIC ACID; FLUORENES; ISOMERISM; MICROWAVES; PEPTIDES;

EID: 33947207869     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.804     Document Type: Article

References (25)

1. Krchnak V, Vagner J. Color-monitored solid-phase multiple peptide synthesis under low-pressure continuous flow conditions. Pept. Res. 1990; 3: 182-193.
2. Yu HM, Chen ST, Wang KT. Enhanced Coupling Efficiency in solid-phase peptide synthesis by microwave irradiation. J. Org. Chem. 1992; 57: 4784-4875.
3. Rabinovich A, Rivier J. Accelerated protocols for solid-phase peptide synthesis at elevated temperature. Am. Biotechnol. Lab. 1994; 12: 48-51.
4. Erdeyli M, Gogoll A. Rapid microwave-assisted solid phase peptide synthesis. Synthesis 2002; 11: 1592-1596.
5. Murray J, Gellman S. Application of microwave irradiation to the synthesis of 14-helical β-peptides. Org. Lett. 2005; 7: 1517-1520.
6. Olivos H, Alluri P, Reddy M, Salony D, Kodadek T. Microwave-assisted solid phase synthesis of peptoids. Org. Lett. 2002; 4: 4057-4059.
7. Collins J, Collins M, Steorts R. Novel method for solid phase peptide synthesis using microwave energy. Poster Presentation at the 18th American Peptide Symposium, Boston, MA, 2003.
8. Matsushita T, Hinou H, Kurogochi M, Shimizu H, Nishimura S. Rapid microwave-assisted solid-phase glycopeptide synthesis. Org. Lett. 2005; 7: 877-880.
9. Fara M, Diaz-Mochon J, 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; 47:1011-1014.
10. Rybka A, Frank H. Microwave sssisted peptide synthesis A tool to replace classical SPPS?. Poster Presentation at the 19th American Peptide Symposium, San Diego, CA, 2005.
11. Atherton E, Sheppard R. In Peptides, Structure and Function; Proceedings of the 9th American Peptide Symposium, Deber C, Hruby V, Kopple K (eds.) Pierce Chemical Co: Rockford, IL, 1985; 415.
12. Merrifleld R, Littau V. In Peptides, Bricas E (ed.). North Holland: Amsterdam: 1968; 179.
13. Han Y, Albericio F, Barany G. Occurrence and minimization of cysteine racemization during stepwise solid-phase peptide synthesis. J. Org. Chem. 1997; 7: 4307-4312.
14. Angell Y, Alsina J, Albericio F, Barany G. Practical protocols for step-wise solid-phase synthesis of cysteine-containing peptides. J. Pept. Res. 2002; 60: 292-299.
15. Hogue Angeletti R, Bibbs L, Bonewald L, Fields G, Kelly J, McMurray J, Moore W, Weintraub S. Analysis of racemization during "standard" solid phase peptide synthesis: a multicenter study. Techniques in Protein Chemistry VIII. Academic Press: San Diego, CA, 1997; 875-890.
16. Kaiser T, Nicholson G, Kohlbau H, Voelter W. Racemization studies of Fmoc-Cys(Trt)-OH during stepwise Fmoc-solid phase peptide synthesis. Tetrahedron Lett. 1990; 37:1187-1190.
17. Nicolas E, Pedroso E, Giralt E. Formation of aspartimide peptides in Asp-Gly sequences. Tetrahedron Lett. 1989; 30: 497-500.
18. Martinez J, Brodansky M. Side reactions in peptide synthesis. Int. J. Pept. Protein Res. 1978; 12: 277-283.
19. Packman L. N-2-Hydroxy-4-methoxybenzyl (Hmb) backbone protection strategy prevents double aspartimide formation in a 'difficult' peptide sequence. Tetrahedron Lett. 1995; 36: 7523-7526.
20. t)-containing peptides. J. Chem. Soc., Chem. Commun. 1994; 7: 853-854.
21. Lauer J, Fields C, Fields G. Sequence dependence of aspartimide formation during 9-fluorenylmethoxycarbonyl solid-phase peptide synthesis. Lett. Pept. Sci. 1994; 1: 197-205.
22. Wade J, Mathieu M, Macris M, Tregear G. Base induced side reactions in Fmoc solid-phase peptide synthesis: Minimization by use of piperazine as N-α-deprotection reagent. Lett. Pept. Sci. 2000; 7: 107-112.
23. Kemp D. In The Peptides: Analysis, Synthesis, Biology, Gross E, Meienhoefer J (eds). Academic Press: New York, 1979; 315.
24. Harding S, Jones J, Sabirov A. Samukov V. im-Trityl protection of histidine. J. Pept. Sci. 1999; 5: 368-373.
25. Mergler M, Dick F, Sax B, Weiler P, Vorherr T. Synthesis and application of Fmoc-His(3-Bum)-OH. J. Pept. Sci. 2001; 7: 502-510.