Manufacturing peptides as active pharmaceutical ingredients

Bibliography

• 1  Kent S. Obituary: Bruce Merrifield (1921–2006). Inventor of solid-phase peptide synthesis. Nature441,824 (2006).
  Medline CASGoogle Scholar
• 2  Merrifield RB. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc.85,2149–2154 (1963).
  CASGoogle Scholar
• 3  Bruckdorfer T, Marder O, Albericio F. From production of peptides in milligram amounts for research to multi-tons quantities for drugs of the future. Curr. Pharm. Biotech.5,29–43 (2004).
  Medline CASGoogle Scholar
• 4  Pichereau C, Allary C. Therapeutic peptides under the spotlight. Eur. Biopharm. Rev.Winter issue,88–93 (2005).
  Google Scholar
• 5  Sehgal A. New Applications In Discovery, Manufacturing, and Therapeutics: Peptides 2006, Research and Markets. D&MD Publications, MA, USA (2006).
  Google Scholar
• 6  Ayoub M, Scheidegger D. Peptide drugs, overcoming the challenges, a growing business. Chem. Today.24,46–48 (2006).
  CASGoogle Scholar
• 7  Bray BL. Innovation: large-scale manufacture of peptide therapeutics by chemical synthesis. Nature Rev. Drug Discovery.2,587–593 (2003).
  Medline CASGoogle Scholar
• 8  Werbitzky O, Brichard MH. Technology for peptide large scale manufacturing: technical, quality, and regulatory challenges. Presented at: TIDES Conference. Taipei, Taiwan, 20 May 2008.
  Google Scholar
• 9  Tam JP, Lu YA. Coupling difficulty associated with interchain clustering and phase transition in solid phase peptide synthesis. J. Am. Chem. Soc.117,12058–12063 (1995).
  CASGoogle Scholar
• 10  Andersson L, Blomberg L, Flegel M, Lepsa L, Nilsson B, Verlander M. Large-scale synthesis of peptides. Biopolymers55,227–250 (2000).
  Medline CASGoogle Scholar
• 11  Lloyd-Williams P, Albericio F, Giralt E. Convergent solid-phase peptide synthesis. Tetrahedron49,11065–11133 (1993).
  CASGoogle Scholar
• 12  Du Vigneaud V, Ressler C, Swan JM, Roberts CW, Katsoyannis PG, Gordon S. The synthesis of an octapeptide amide with the hormonal activity of oxytocin. J. Am. Chem. Soc.75,4879–4880 (1953).
  CASGoogle Scholar
• 13  Werbitzky O, Oehlers D. Manufacturing peptide APIs in the scope of upcoming new challenges higher complexity and industrialization. Chem. Today26,26–28 (2008).
  CASGoogle Scholar
• 14  Miranda LP, Alewood PF. Challenges for protein chemical synthesis in the 21st century: bridging genomics and proteomics. Biopolymers55,217–226 (2000).
  Medline CASGoogle Scholar
• 15  Garcia Martin F, Albericio F. Solid supports for the synthesis of peptides. From the first resin used to the most sophisticated in the market. Chem. Today26,29–34 (2008).
  Google Scholar
• 16  Albericio F, Chinchilla R, Dodsworth DJ, Najera C. New trends in peptide coupling reagents. Org. Prep. Proc. Int.33,203–303 (2001).
  CASGoogle Scholar
• 17  Albericio F. Developments in peptide and amide synthesis. Curr. Opin. Chem. Biol.8,211–221 (2004).
  Medline CASGoogle Scholar
• 18  Carpino LA, Han GY. The 9-fluorenylmethoxycarbonyl function, a new base-sensitive amino-protecting group. J. Am. Chem. Soc.92,5748–5749 (1970).
  CASGoogle Scholar
• 19  Kimmerlin T, Seebach D. 100 years of peptide synthesis: ligation methods for peptide and protein synthesis with applications to b-peptide assemblies. J. Pep. Res.65,229–260 (2005).
  Medline CASGoogle Scholar
• 20  García-Martín F, Quintanar-Audelo M, García-Ramos Y et al. ChemMatrix, a poly(ethylene glycol)-based support for the solid-phase synthesis of complex peptides. J. Comb. Chem.8,213–220 (2006).
  Medline CASGoogle Scholar
• 21  Albericio F, van Abel R, Barany G. Solid-phase synthesis of peptides with C-terminal asparagine or glutamine. Int. J. Peptide Protein Res.35,284–286 (1990).
  Medline CASGoogle Scholar
• 22  Mutter M, Nefzi A, Sato T, Sun X, Wahl F, Wuhr T. Pseudo-prolines (ψ Pro) for accessing inaccessible peptides. Peptide Res.8,145–153 (1995).
  Medline CASGoogle Scholar
• 23  García-Martín F, White P, Steinauer R, Côté S, Tulla-Puche J, Albericio F. The synergy of ChemMatrix resin and pseudoproline building blocks renders Rantes, a complex aggregated chemokine. Biopolymers84,566–575 (2006).
  Medline CASGoogle Scholar
• 24  Vázquez J, Qushair G, Albericio F. Qualitative colorimetric tests for solid phase synthesis. In: Methods in Enzymology (Volume 369) Morales G (Ed.). Academic Press, CA, USA 21–35 (2003).
  Google Scholar
• 25  Drucker DJ, Nauck MA. The incretin system: glucagon-like peptide-1 receptor agonists and dipeptidyl peptidase-4 inhibitors in type 2 diabetes. Lancet368,1696–1705 (2006).
  Medline CASGoogle Scholar
• 26  Blonde L, Klein EJ, Han J et al. Interim analysis of the effects of exenatide treatment on A1C, weight and cardiovascular risk factors over 82 weeks in 314 overweight patients with type 2 diabetes. Diabetes Obes. Metab.8,436–447 (2006).
  Medline CASGoogle Scholar
• 27  Nauck MA, Hompesch M, Filipczak R, Le TD, Zdravkovic M, Gumprecht J; NN2211–1499 Study Group. Five weeks of treatment with the GLP-1 analogue liraglutide improves glycaemic control and lowers body weight in subjects with Type 2 diabetes. Exp. Clin. Endocrinol. Diabetes114,417–423 (2006).
  Medline CASGoogle Scholar
• 28  Madsen K, Knudsen LB, Agersoe H et al. Structure–activity and protraction relationship of long-acting glucagon-like peptide-1 derivatives: importance of fatty acid length, polarity, and bulkiness. J. Med. Chem.50,6126–6132 (2007).
  Medline CASGoogle Scholar
• 29  Williams JA, Day M, Heavner JE. Ziconotide: an update and review. Expert Opin. Pharmacother.9,1575–1583 (2008).
  Medline CASGoogle Scholar
• 30  Bodanszky M. Peptide Chemistry: a Practical Textbook. Springer-Verlag, Berlin, Germany (1988).
  Google Scholar
• 31  Sieber P. A new acid-labile anchor group for the solid-phase synthesis of C-terminal peptide amides by the Fmoc method. Tetrahedron Lett.28,2107–2110 (1987).
  CASGoogle Scholar
• 32  Barlos K, Gatos D, Kallitsis J et al. Darstellung geshutzter peptid-fragmente unter einsatz substituierter triphenylmethyl-harze. Tetrahedron Lett.30,3943–3946 (1989).
  CASGoogle Scholar
• 33  Barlos K, Gatos D, Kapolos S, Papaphotiu G, Schäfer W, Wenqing Y. Veresterung von partiell geschutzten peptid-fragmenten mit harzen. Einsatz von 2-chlortritylchlorid zur synthese von Leu15-gastrin I. Tetrahedron Lett.30,3947–3950 (1989).
  CASGoogle Scholar
• 34  Eipper BA, Milgram SL, Husten EJ, Yun HY, Mains RE. Peptidylglycine α-amidating monooxygenase: a multifunctional protein with catalytic, processing, and routing domains. Protein Sci.2,489–497 (1993).
  Medline CASGoogle Scholar
• 35  Bradbury AF, Finnie MDA, Smyth DG. Mechanism of C-terminal amide formation by pituitary enzymes. Nature298,686–688 (1982).
  Medline CASGoogle Scholar
• 36  Katopodis AG, Ping D, May SW. A novel enzyme from bovine neurointermediate pituitary catalyzes dealkylation of α-hydroxyglycine derivatives, thereby functioning sequentially with peptidylglycine α-amidating monooxygenase in peptide amidation. Biochemistry29,6115–6120 (1990).
  Medline CASGoogle Scholar
• 37  Dawson PE, Muir TW, Clark-Lewis I, Kent SB. Synthesis of proteins by native chemical ligation. Science266,776–779 (1994).
  Medline CASGoogle Scholar
• 38  Dawson PE, Kent SB. Synthesis of native proteins by chemical ligation. Annu. Rev. Biochem.69,923–960 (2000).
  Medline CASGoogle Scholar
• 39  Macmillan D. Evolving strategies for protein synthesis converge on native chemical ligation. Angew. Chem. Int. Ed.45,7668–7672 (2006).
  Medline CASGoogle Scholar
• 40  Gill I, López-Fandiño R, Jorba X, Vulfson EN. Biologically active peptides and enzymatic approaches to their production. Enzyme Microb. Technol.18,163–183 (1996).
  Medline CASGoogle Scholar
• 41  Kumar D, Bhalla TC. Microbial proteases in peptide synthesis: approaches and applications. Appl. Microbiol. Biotechnol.68,726–736 (2005).
  Medline CASGoogle Scholar
• 42  Garoff H. Using recombinant DNA techniques to study protein targeting in the eucaryotic cell. Ann. Rev. Cell Biol.1,403–445 (1985).
  Medline CASGoogle Scholar
• 43  Wallace CJA. Protein Engineering by Semisynthesis. CRC Press, FL, USA (2000).
  Google Scholar
• 44  Lloyd-Williams P, Albericio F, Giralt E. Chemical Approaches to the Synthesis of Peptides and Proteins. CRC Press, FL, USA (1997).
  Google Scholar
• 45  Sallam LA, El-Refai AM, Hamdi AH, El-Minofi HA, Abd-Elsalam IS. Studies on the application of immobilization technique for the production of cyclosporin A by a local strain of Aspergillus terreusJ. Gen. Appl. Microbiol.51,143–149 (2005).
  Medline CASGoogle Scholar
• 46  Agathos SN, Madhosingh C, Marshall JW, Lee J. The fungal production of cyclosporine. Ann. NY Acad. Sci.506,657–662 (1987).
  Medline CASGoogle Scholar
• 47  Sekar C, Balaraman K. Optimization studies on the production of cyclosporin A by solid state fermentation. Biol. Eng.18,293–296 (1998).
  CASGoogle Scholar
• 48  Nisha AK, Meignanalakshmi S, Ramasamy K. Comparative effect of amino acids in the production of cyclosporin by solid and submerged fermentation. Biotechnology7,205–208 (2008).
  CASGoogle Scholar
• 49  Metha NM. Oral delivery and recombinant production of peptide hormones. Part II. Recombinant production of therapeutic peptides. BioPharm. Inter. July, 7–9 (2004).
  Google Scholar
• 50  Shuman HA, Silhavy TJ. The art and design of genetic screens: Escherichia coli. Nat. Rev. Genet.4,419–431 (2003).
  Medline CASGoogle Scholar
• 51  Won JI, Barron AE. A new cloning method for the preparation of long repetitive polypeptides without a sequence requirement. Macromolecules35,8281–8287 (2002).
  CASGoogle Scholar
• 52  De Wit H. Presented at: TIDES Conference. Las Vegas, NV, USA, 25–29 April 2004.
  Google Scholar
• 53  Frost Sullivan. Strategic Analysis of the Therapeutic Peptides Market in Europe. San Antonio, TX, USA (2004).
  Google Scholar
• 101  Scientific discussion www.emea.europa.eu/humandocs/PDFs/EPAR/angiox/103304en6.pdf
  Google Scholar
• 102  Center for Drug Evaluation and Research: Chemistry review(s) www.fda.gov/cder/foi/nda/2005/021406s000_ChemR.pdf
  Google Scholar
• 201  Ho G, Paone A, Forni L, Detollenaere C, Bonnett B. Processes for preparing eptifibatide and pertinent intermediate compounds. WO05100381 (2005).
  Google Scholar
• 202  Cote S. New polyether based monomers, crosslinkers, and highly crosslinked amphiphile polyether resins. WO012277 (2005).
  Google Scholar
• 203  Albericio F, Cruz LJ, Garcia-Martin F, Tulla-Puche J. Peptide synthesis of α-helixes on PEG resin. WO108594 (2006).
  Google Scholar
• 204  Giraud M, Albericio F, Quattrini F, Werbitzky O, Senn K, Williner M. Method for peptide synthesis. WO040536 (2008).
  Google Scholar
• 205  Werbitzky O, Varray S, Giraud M, Meininghaus C. Use of pseudoproline dipeptides in an improved solid phase synthesis of glucagon-like peptides. WO090496 (2007).
  Google Scholar
• 206  Varray S, Werbitzky O, Zeiter T. On-resin peptide cyclization. WO06045483 (2006).
  Google Scholar
• 207  Knudsen LB, Sorensen PO, Nielsen PF. GLP-1 derivatives. WO9808871 (1998).
  Google Scholar
• 208  Giraud M, Williner M, Werbitzky O. Method for the synthesis of peptide amides. WO008050 (2006).
  Google Scholar
• 209  Ko SY, Kobel H, Besemer-Rosenwirth B et al. Cyclosporin fermentation process. US6255100 (2001).
  Google Scholar