Large-scale manufacture of peptide therapeutics by chemical synthesis

Nature Reviews Drug Discovery

Volumn 2, Issue 7, 2003, Pages 587-593

  Bray, Brian L ^a  

^a Trimeris Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANGIOPEPTIN; ATOSIBAN; CORTICOTROPIN; CORTICOTROPIN RELEASING FACTOR; DESMOPRESSIN; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; ENALAPRIL; ENFUVIRTIDE; EPTIFIBATIDE; FELYPRESSIN; GONADORELIN; GONADORELIN AGONIST; GONADORELIN ANTAGONIST; GROWTH HORMONE RELEASING FACTOR; HIRULOG; LEUPRORELIN; LISINOPRIL; LYPRESSIN; OCTREOTIDE; OXYTOCIN; SOMATOSTATIN; SOMATOSTATIN DERIVATIVE; SYNTHETIC PEPTIDE; TERLIPRESSIN; THYMOPENTIN; THYMOSIN ALPHA1; UNINDEXED DRUG; VASOPRESSIN; VASOPRESSIN DERIVATIVE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; GLYCOPROTEIN GP 41; PEPTIDE FRAGMENT;

ARTICLE; CAPITAL; COMMERCIAL PHENOMENA; DRUG MANUFACTURE; DRUG QUALITY; GOOD MANUFACTURING PRACTICE; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; MEMBRANE FUSION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROFIT; SCALE UP; REVIEW; SYNTHESIS;

ANTI-HIV AGENTS; HIV ENVELOPE PROTEIN GP41; PEPTIDE FRAGMENTS;

EID: 0037667047     PISSN: 14741776     EISSN: None     Source Type: Journal    
DOI: 10.1038/nrd1133     Document Type: Article

References (26)

1. Kelley, W. S. Therapeutic peptides: the devil is in the detail. Biotechnol. 14, 28-31 (1996).
2. Fields, G. F. and Nobel, R. L. Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Int. J. Peptide Protein Res. 35, 161-214 (1990).
3. Chan, W. C. & White, P. D. Fmoc Solid Phase Peptide Synthesis - A Practical Approach (Oxford University Press, Oxford, 2000).
4. Bodanszky, M. Principles of Peptide Synthesis (Springer, Heidelberg, 1993).
5. Merrifield, R. B. Solid phase peptide synthesis. 1. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 85, 2149-2154 (1963).
6. Carpino, L. A. & Han, G. Y 9-Fluorenylmethoxycarbonyl function, a new base-sensitive amino-protecting group. J. Am. Chem. Soc. 92, 5748-5749 (1970).
7. Carpino, L. A. & Han, G. Y. 9-Fluorenylmethoxycarbonyl amino-protecting group. J. Org. Chem. 37, 3404-3409 (1972).
8. Carpino, L. A. New amino-protecting groups in organic synthesis. Acc. Chem. Res. 6, 191-198 (1973).
9. Chang, C. D. & Meienhofer, J. Solid-phase peptide synthesis using mild base cleavage of N-α-fluorenylmethyloxycarbonylamino acids, exemplified by a synthesis of dihydrosomatostatin. Int. J. Pept. Protein Res. 11, 246-249 (1978).
10. Atherton, E. et al. A mild procedure for peptide synthesis: use of fluorenylmethoxycarbonylamino-acids. J. Chem. Soc., Chem. Comm. 13, 537-539 (1978).
11. Atherton, E., Fox, H., Harkiss, D. & Sheppard, R. C. Application of polyamide resins to polypeptide synthesis: an improved synthesis of β-endorphin using fluorenylmethoxycarbonylamino-acids. J. Chem. Soc., Chem. Comm. 13, 539-540 (1978).
12. Rink, H. Solid-phase synthesis of protected peptide fragments using a trialkoxy-diphenyl-methyl ester resin. Tetrahedron Lett. 28, 3787 (1987).
13. Immer, H. U. in Proceedings of the 11th American Peptide Symposium (eds Rivier, J. E. & Marshall, G. R.) 1054 (ESCOM, Leidon, 1990).
14. Florsheimer, A. & Riniker, B. in Peptide 1990 (Proceedings of the 21st European Peptide Symposium) (eds Giralt, E.,& Andreu, D) 131-133 (ESCOM, Leiden, 1991).
15. Barlos, K. et al. Darstellung geshutzter peptid-fragmente unter einsatz substituierter triphenylmethyl-harze. Tetrahedron Lett. 30, 3943-3946 (1989).
16. 15-gastrin I. Tetrahedron Lett. 30, 3947-3950 (1989).
17. Megler, M., Nyfeler, R., Tanner, R., Gosteli, J. & Grogg, P. Peptide synthesis by a combination of solid-phase and solution methods II, synthesis of fully protected peptide fragments on 2-methoxy-4-alkoxy-benzyl alcohol resin. Tetrahedron Lett. 32, 4009-4012 (1988).
18. Barlos, K., Gatos, D. & Schafer, W. Synthesis of prothymosin α (ProTα) - a protein consisting of 109 amino acid residues. Angew. Chem. Int. Ed. Engl. 30, 590-593 (1991).
19. Riniker, B., Florsheimer, A., Fretz, H., Sieber, P & Kamber, B. A general strategy for the synthesis of large peptides: The combined solid-phase and solution approach. Tetrahedron 49, 9307-9320 (1993).
20. Kang, M. C., Bray, B., Lichty, M., Mader, C. & Merutka, G. Methods and composition for peptide synthesis (T-20). US Patent 6, 015, 881 (2000).
21. Harre, M., Nickisch, K. & Tilstam, U. An efficient method for activation and recycling of trityl resins. React. Funct. Polymers 41, 111-114 (1998).
22. Benoiton, N., Lee, Y. & Chen, F. in Proceedings of the 12th American Peptide Symposium Peptides; Chemistry & Biology, 496-498 (ESCOM, Leidon, 1992).
23. Cameron, L., Holder, J., Meldal, M. & Sheppard, R. Peptide synthesis. Part 13. Feedback control in solid phase synthesis. Use of fluorenylmethoxycarbonyl amino acid 3,4-dihydroxy-4-oxo-1,2,3-benzotriazin-3-yl esters in fully automated system. J. Chem. Soc. Perkin Trans. 1, 2895-2901 (1988).
24. Milton, R., Milton, S. & Adams, F. Prediction of difficult sequences in solid-phase peptide synthesis. J. Am. Chem. Soc. 112, 6039-6046 (1990).
25. Knorr, R., Trzeciak, A., Bannwarth, W. & Gillessen, D. New coupling reagents in peptide chemistry. Tetrahedron Lett. 30, 1927-1930 (1989).
26. Konig, W. & Geiger, R. New method for the synthesis of peptides: Activation of the carbonyl group with dicyclohexylcarbodiimide by using 1-hydroxybenzotriazoles as additives. Ber. Dtsch. Chem. Ges. 103, 788 (1970).