Organic solvent nanofiltration: A new paradigm in peptide synthesis

Organic Process Research and Development

Volumn 14, Issue 6, 2010, Pages 1313-1325

  So, Sheung ^a   Peeva, Ludmila G ^a   Tate, Edward W ^a   Leatherbarrow, Robin J ^a   Livingston, Andrew G ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID SEQUENCE; COUPLING CHEMISTRY; DEPROTECTION; DIAFILTRATION; EMERGING TECHNOLOGIES; MASS TRANSFER LIMITATION; MOLECULAR SEPARATION; NEW TECHNOLOGIES; ORGANIC SOLVENT NANOFILTRATION; PENTAPEPTIDES; PEPTIDE SYNTHESIS; PRODUCTION SCALE; PROTECTING GROUP; SOLID PHASE SYNTHESIS; SOLID-PHASE; SOLUTION PHASE SYNTHESIS; STABLE MEMBRANES;

AMINO ACIDS; BYPRODUCTS; FUNCTIONAL GROUPS; NANOFILTRATION; ORGANIC SOLVENTS; PEPTIDES; POLYETHYLENE GLYCOLS; POLYETHYLENE OXIDES;

SYNTHESIS (CHEMICAL);

EID: 78649643372     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op1001403     Document Type: Article

References (49)

1. Glaser, V. Genet. Eng. Biotechnol. News 2009, 29, 1-4
2. Vlieghe, P.; Lisowski, V.; Martinez, J.; Khrestchatisk, M. Drug Discovery Today 2010, 15, 40-56
3. Tsuru, T.; Nakao, S.; Kimura, S.; Shutou, T. Sep. Sci. Technol. 1994, 29, 971-984
4. Li, S.-L.; Li, C.; Lui, Y.-S.; Wang, X.-L.; Cao, Z.-A. J. Membr. Sci. 2003, 222, 191-201
5. Wang, X.; Ying, A.; Wang, W. J. Membr. Sci. 2002, 196, 59-67
6. Bayer, E.; Mutter, M. Nature 1972, 237, 512-513
7. Bayer, E.; Gillessen, D.; Kuenzi, H.; Mutter, M.; Studer, R. A process for the manufacture of peptides. (F. Hoffmann-La Roche & Co.)., DE-F2047413, 1980.
8. Bayer, E.; Mutter, M.; Uhmann, R.; Polster, J.; Mauser, H. J. Am. Chem. Soc. 1974, 96, 7333-7336
9. Gut, V.; Rudinger, J. Peptides 1968; E. Bricas: Amsterdam, 1968; pp 185 - 188.
10. Edelstein, M.; Scott, P. E.; Sherlund, M.; Hansen, A. L.; Hughes, J. L. Chem. Eng. Sci. 1986, 41, 617-624
11. Fields, G.; Fields, C. J. Am. Chem. Soc. 1991, 113, 4202
12. Amblard, M.; Fehrentz, J.; Martinez, J.; Subra, G. Mol. Biotechnol. 2006, 33, 239-254
13. Chan, W.; White, P. Fmoc solid phase peptide synthesis: a practical approach; Oxford University Press: Oxford, 2000.
14. Barlos, K.; Gatos, D.; Kapolos, S.; Poulos, C.; Schafer, W.; Wenqing, Y. Int. J. Pept. Protein Res. 1991, 38, 555-561
15. Livingston, A.; Peeva, L.; Han, S. J.; Nair, D.; Luthra, S. S.; White, L. S.; Freitas Dos Santos, L. M. Ann. N.Y. Acad. Sci. 2003, 984, 123-141
16. Wong, H. T.; See-Toh, Y. H.; Ferreira, F. C.; Crook, R.; Livingston, A. G. Chem. Commun. 2006, 19, 2063-2065
17. Wong, H. T.; Pink, C. J.; Ferreira, F. C.; Livingston, A. G. Green Chem. 2006, 8, 373-379
18. So, S.; Peeva, L. G.; Tate, E. W.; Leatherbarrow, R. J.; Livingston, A. G. Chem. Commun. 2010, 46, 2808-2810
19. Toniolo, C.; Bonora, G. M.; Mutter, M. J. Am. Chem. Soc. 1979, 101, 450-454
20. Fischer, P.; Zheleva, D. J. Pept. Sci. 2002, 8, 529-542
21. Drioli, S.; Adamo, I.; Ballico, M.; Morvan, F.; Bonora, G. M. Eur. J. Org. Chem. 2002, 3473-3480
22. Bonora, G. M.; Rossin, R.; Zaramella, S.; Cole, D. L.; Eleuteri, A.; Ravikumar, V. T. Org. Process Res. Dev. 2000, 4, 225-231
23. Wentworth, P., Jr. Trends Biotechnol 1999, 17, 448-452
24. Gravert, D. J.; Janda, K. D. Curr. Opin. Chem. Biol. 1997, 1, 107-113
25. Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509
26. Basu, A.; Yang, K.; Wang, M.; Liu, S.; Chintala, R.; Palm, T.; Zhao, H.; Peng, P.; Wu, D.; Zhang, Z.; Hua, J.; Hsieh, M.-C.; Zhou, J.; Petti, G.; Li, X.; Janjua, A.; Mendez, M.; Liu, J.; Longley, C.; Zhang, Z.; Mehlig, M.; Borowski, V.; Viswanathan, M.; Filpula, D. Bioconjugate Chem. 2006, 17, 618-630
27. Lee, S.-H.; Lee, S.; Youn, Y. S.; Na, D. H.; Chae, S. Y.; Byun, Y.; Lee, K. C. Bioconjugate Chem. 2005, 16, 377-382
28. Roberts, M.; Bentley, M.; Harris, J. Adv. Drug Delivery Rev. 2002, 54, 459-476
29. Akula, K. C.; Boddy, K.; Doma, U. Indian J. Chem. 2006, 45B, 678-683
30. Vandezande, P.; Gevers, L.; Vankelecom, I. Chem. Soc. Rev. 2008, 37, 365-405
31. Toh, Y. S.; Lim, F.; Livingston, A. J. Membr. Sci. 2007, 301, 3-10
32. Pillai, V.; Mutter, M.; Bayer, E.; Gatfield, I. J. Org. Chem. 1980, 45, 5364-5370
33. Wang, X.-L.; Tsuru, T.; Nakao, S.; Kimura, S. J. Membr. Sci. 1997, 135, 19-32
34. Toon, Y.; Lueptow, R. J. Membr. Sci. 2005, 261, 76-86
35. Kiso, Y.; Sugiura, Y.; Kitao, T.; Nishimura, K. J. Membr. Sci. 2001, 192, 1-10
36. Kiso, Y.; Kon, T.; Kitao, T.; Nishimura, K. J. Membr. Sci. 2001, 182, 205-214
37. Kiso, Y.; Nishimura, Y.; Kitao, T.; Nishimura, K. J. Membr. Sci. 2000, 171, 229-237
38. Donnan, F. J. Membr. Sci. 1995, 100, 45-55
39. Martin-Orue, C.; Bouhallab, S.; Garem, A. J. Membr. Sci. 1998, 142, 225-233
40. Tsuru, T.; Nakao, S.; Kimura, S.; Shutou, T. Sep. Sci. Technol. 1994, 29, 971-984
41. Carpino, L.; El-Faham, A.; Albericio, F. Tetrahedron Lett. 1994, 35, 2279-2282
42. http://duramem.evonik.com/product/duramem-puramem/en/Pages/default.aspx.
43. Vankelecom, I.; De Smet, K.; Gevers, L.; Livingston, A.; Nair, D.; Aerts, S.; Kuypers, S.; Jacobs, P. J. Membr. Sci. 2004, 231, 99-108
44. Peeva, L.; Gibbins, E.; Luthra, S.; White, L.; Stateva, R.; Livingston, A. J. Membr. Sci. 2004, 236, 121-136
45. http://www.kochmembrane.com.
46. http://www.sterlitech.com.
47. http://www.inopor.com.
48. Ochoa, E.; Medrano, S.; de Carlin, M.; Dilonardo, A. Cell. Mol. Neurobiol. 1988, 8, 325-331
49. Katakai, R. Bull. Chem. Soc. Jpn. 1977, 50, 1173-1178