Peptide amidation: Production of peptide hormones in vivo and in vitro

Biotechnology and Bioprocess Engineering

Volumn 6, Issue 4, 2001, Pages 244-251

  Kim, Kyun Hwan ^a   Seong, Baik L ^b  

^a Yonsei University   (South Korea)

^b Protheon Incorporated   (South Korea)

Author keywords

Amidating enzyme; Calcitonin; PAM; Peptide amide; Peptide hormone; PHM

Indexed keywords

EID: 4544386057     PISSN: 12268372     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02931985     Document Type: Article

References (58)

1. Hook, V. Y., A. V. Azaryan, S. R. Hwang, and N. Tezapsidis (1994) Proteases and the emerging role of protease inhibitors in prohormone processing. FASEB J. 8: 1269-1278.
2. Bennett, H. P. J., A. F. Bradbury, and W. B. Hutter (1993) Processing of pro-peptides: Glycosylation, phosphorylation, sulfation, acetylation and amidation. pp. 251-288. In: Y. P. Loh, (ed.). Mechanisms of Intracellular Trafficking and Processing of Prohormones. CRC Press. Boca Raton. FL, USA.
3. Eipper, B. A. and R. E. Mains (1988) Peptide alpha-amidation. Annu. Rev. Physiol. 50: 333-44.
4. Eipper, B. A., D. A. Stoffers, and R. E. Mains (1992) The biosynthesis of neuropeptides: peptide alpha-amidation. Annu. Rev. Neurosci. 15: 57-85.
5. Bradbury, A. F., M. D. Finnie, and D. G. Smyth (1982) Mechanism of C-terminal amide formation by pituitary enzymes. Nature 298: 686-688.
6. Eipper, B. A., S. N. Perkins, E. J. Husten, R. C. Johnson, H. T. Keutmann, and R. E. Mains (1991) Peptidyl-alpha-hydroxyglycine alpha-amidating lyase: Purification, characterization, and expression. J. Biol. Chem. 266: 7827-7833.
7. Perkins, S. N., E. J. Husten, and B. A. Eipper (1990) The 108-kDA peptidylglycine alpha-amidating monooxygenase precursor contains two separable enzymatic activities involved in peptide amidation. Biochem. Biophys. Res. Commun. 171: 926-932.
8. Takahashi, K., H. Okamoto, H. Seino, and M. Noguchi (1990) Peptidylglycine alpha-amidating reaction: evidence for a two-step mechanism involving a stable intermediate at neutral pH. Biochem. Biophys. Res. Commun. 169: 524-530.
9. Husten, E. J. and E. A. Eipper (1991) The membrane-bound bifunctional peptidylglycine alpha-amidating monooxygenase protein. Exploration of its domain structure through limited proteolysis. J. Biol. Chem. 266: 17004-17010.
10. Eipper, B. A., C. B. Green, T. A. Campbell, D. A. Stoffers, H. T. Keutmann, R. E. Mains, and L. Ouafik (1992) Alternative splicing and endoproteolytic processing generate tissue-specific forms of pituitary peptidylglycine alpha-amidating monooxygenase (PAM). J. Biol. Chem. 267: 4008-4015.
11. Prigge, S. Tj, R. E. Mains, B. A. Eipper, and L. M. Amzel (2000) New insights into copper monooxygenases and peptide amidation: structure, mechanism and function. Cell Mol. Life Sci. 57: 1236-1259.
12. Eipper, B. A., S. L. Milgram, E. J. Husten, H. Y. Yun, and R. E. Mains (1993) Peptidylglycine alpha-amidating monooxygenase: a multifunctional protein with catalytic, processing, and routing domains. Protein Sci. 2: 489-497.
13. Oldham, C. D., C. Li, P. R. Girard, R. M. Nerem, and S. W. May (1992) Peptide amidating enzymes are present in cultured endothelial cells. Biochem. Biophys. Res. Commun. 184: 323-329.
14. Saldise, L., A. Martinez, L. M. Montuenga, A. Treston, D. R. Springall, J. M. Polak, and J. J. Vazquez (1996) Distribution of peptidyl-glycine alpha-amidating monooxygenase (PAM) enzymes in normal human lung and in lung epithelial tumors. J. Histochem. Cytochem. 44: 3-12.
15. Ogonowski, A. A., S. W. May, A. B. Moore, L. T. Barrett, C. L. O'Bryant, and S. H. Pollock (1997) Antiinflammatory and analgesic activity of an inhibitor of neuropeptide amidation. J. Pharmacol. Exp. Ther. 280: 846-853.
16. Klein, R. S. and L. D. Fricker (1992) Heterogeneous expression of carboxypeptidase E and proenkephalin mRNAs by cultured astrocytes. Brain Res. 569: 300-310.
17. Jaworsky D. E., B. A. Eipper, and G. V. Ronnett (1999) Expression of PAM and amidated neuropeptides in developing and adult rat olfactory epithelium. Soc. Neurosci. 29th Ann. Mtg. Abst. 428. 10.
18. Kolhekar, A. S., M. S. Roberts, N. Jiang, R. C. Johnson, R. E. Mains, B. A. Eipper, and P. H. Taghert (1997) Neuropeptide amidation in Drosophila: separate genes encode the two enzymes catalyzing amidation. J. Neurosci. 17: 1363-1376.
19. Scopsi, L., R. Lee, M. Gullo, P. Collini, E. J. Husten, and B. A. Eipper (1998) Peptidylglycine alpha-amidating monooxygenase in neuroendocrine tumors. Appl. Immunohistochem. 6: 120-132.
20. Ouafik, L. H., D. A. Stoffers, T. A. Campbell, R. C. Johnson, B. T. Bloomquist, R. E. Mains, and B. A. Eipper (1992) The multifunctional peptidylglycine alpha-amidating monooxygenase gene: exon/intron organization of catalytic, processing, and routing domains. Mol. Endocrinol. 6: 1571-1584.
21. Stoffers, D. A., L. Ouafik, and B. A. Eipper (1991) Characterization of novel mRNAs encoding enzymes involved in peptide alpha-amidation. J. Biol. Chem. 266: 1701-1707.
22. Husten, E. J. and B. A. Eipper (1994) Purification and characterization of PAM-1, an integral membrane protein involved in peptide processing. Arch. Biochem. Biophys. 312: 487-492.
23. Prigge, S. T., A. B. Kolhekar, B. A. Eipper, R. E. Mains, and L. M. Amzel (1997) Amidation of bioactive peptides: the structure of peptidylglycine alpha-hydroxylating monooxygenase. Science. 278: 1300-1305.
24. Freeman, J. C. I. J. Villafranca, and D. J. Merkler (1993) Redox cycling of enzyme-bound copper during peptide amidation. J. Am. Chem. Soc. 115: 4923-4924.
25. Prigge, S. T., A. S. Kolhekar, B. A. Eipper, R. E. Mains, and L. M. Amzel (1999) Substrate-mediated electron transfer in peptidylglycine alpha-hydroxylating monooxygenase. Nat. Struct. Biol. 6: 976-683.
26. Moore, H. P. and R. B. Kelly (1985) Secretory protein targeting in a pituitary cell line: differential transport of foreign secretory proteins to distinct secretory pathways. J. Cell Biol. 101: 1773-1781.
27. Dickerson, I. M. and R. E. Mains (1990) Cell-type specific posttranslational processing of peptides by different pituitary cell lines. Endocrinology 127: 133-140.
28. Merli, S., S. De Falco, A. Verdoliva, M. Tortora, M. Villain, P. Silvi, G. Cassani, and G. Fassina (1996) An expression system for the single-step production of recombinant human amidated calcitonin. Protein Expr. Purif. 7: 347-354.
29. Takahashi, K. I., Y. C. Liu, N. Hayashi, E. Goto, M. Kato, H. Kawashima, and T. Takeuchi (1997) Production of bioactive salmon calcitonin from the nonendocrine cell lines COS-7 and CHO. Peptides. 18: 439-444.
30. Hayashi, N., T. Kayo, K. Sugano, and T. Takeuchi (1994) Production of bioactive gastrin from the non-endocrine cell lines CHO and COS-7. FEBS Lett. 337: 27-32.
31. Mizuno, K., K. Ohsuye, Y. Wada, K. Fuchimura, S. Tanaka, and H. Matsuo (1987) Cloning and sequence of cDNA encoding a peptide C-terminal alpha-amidating enzyme from Xenopus laevis. Biochem. Biophys. Res. Commun. 148: 546-552.
32. Ohsuye, K., K. Kitano, Y. Wada, K. Fuchimura, S. Tanaka, K. Mizuno, H. and H. Matsuo (1988) Cloning of cDNA encoding a new peptide C-terminal alpha-amidating enzyme having a putative membrane-spanning domain from Xenopus laevis skin. Biochem. Biophys. Res. Commun. 150: 1275-1281.
33. Miller, D. A., K. U. Sayad, R. Kulathila, G. A. Beaudry, D. J. Merkler, and A. H. Bertelsen (1992) Characterization of a bifunctional peptidylglycine alpha-amidating enzyme expressed in Chinese hamster ovary cells. Arch. Biochem. Biophys. 298: 380-388.
34. Ray, M. V., D. P. Van, A. H. Bertelsen, D. E. Jackson-Matthews, A. M. Sturmer, D. J. Merkler, A. P. Consalvo, S. D. Young, J. P. Gilligan, and P. P. Shields (1993) Production of recombinant salmon calcitonin by in vitro amidation of an Escherichia coli produced precursor peptide. Biotechnology (N Y). 11: 64-70.
35. Henriksen, D. B., M. Rolland, M. H. Jakobsen, O. Buchard, and K. Breddam (1992) C-terminal amidation of calcitonin by carboxypeptidase Y catalyzed transpeptidation with a photocleavable nucleophile. Pept. Res. 5: 321-324.
36. Henriksen, D. B., K. Breddam, and O. Buchardt (1993) Peptide amidation by enzymatic transacylation and photolysis. Int. J. Pept. Protein Res. 41: 169-180.
37. Breddam, K., F. Widmer, and M. Meldal (1991) Amidation of growth hormone releasing factor (1-29) by serine carboxypeptidase catalysed transpeptidation. Int. J. Pept. Protein Res. 37: 153-160.
38. Bongers, J., R. E. Offord, A. M. Felix, T. Lambros, W. Liu, M. Ahmad, R. M. Campbell, and E. P. Heimer (1991) Comparison of enzymatic semisyntheses of peptide amides: human growth hormone releasing factor and analogs. Biomed. Biochim. Acta. 50: S157-162.
39. Bongers, J., W. Liu, T. Lambros, K. Breddam, R. M. Campbell, A. M. Felix, and E. P. Heimer (1994) Peptide synthesis catalyzed by the Glu/Asp-specific endopeptidase. Influence of the ester leaving group of the acyl donor on yield and catalytic efficiency. Int. J. Pept. Protein Res. 44: 123-129.
40. Hong, D., M. Zhuang, M. Li, C. Chen, and J. Mao (2000) Production of recombinant salmon calcitonin by amidation of precursor peptide using enzymatic transacylation and photolysis in vitro. Biochem. Biophys. Res. Commun. 267: 362-367.
41. Vladislav, D. V. and K. A. Marxovich (1996) Solution phase synthesis of immunoregulating peptides. PCT Int. Appl. WO 9,626,955.
42. Fernando, A. and G. Barany (1987) An acid-labile anchoring linkage for solid-phase synthesis of C-terminal peptide amides under mild conditions. Int. J. Peptide Protein Res. 30: 206-216.
43. Orlowski, R. C., R. Walter, and D. Winkler (1976) Study of benzhydrylamine-type polymers. Synthesis and use of ρ-methoxybenzhydrylamine resin in the solid-phase preparation of peptides. J. Org. Chem. 41: 3701-3705.
44. Rink, H. (1987) Solid-phase synthesis of protected peptide fragments using a trialkoxy-diprienyl-methyl ester resin. Tetrahedron Lett. 28: 3787-3790.
45. Mizuno, M., H. Katsuji, I. Reiko, M. Ikuyo, K. Toru, A. Saburo, Y. Kenji, and J. Toshiyuki (1999) Synthesis of a glycopeptide containing oligosaccharides: Chemoenzymatic synthesis of eel calcitonin analogues having natural N-linked oligosaccharides. J. Am. Chem. Soc. 121: 284-290.
46. Velentza, A., S. Spiliou, C. P. Poulos, and G. J. Goldsworthy (2000) Synthesis and biological activity of adipokinetic hormone analogues with modifications in the 4-8 region. Peptides 21: 631-637.
47. Scott, W. L., D. Francisca, L. Karen, S. P. Richard, and J. O. Martin (2001) Solid-phase synthesis of amino amides and peptide amides with unnatural side chains. Tetrhedron Lett. 42: 2073-2076.
48. Han, Y., S. L. Bontems, P. Hegyes, M. C. Munson, C. A. Minor, S. A. Kates, F. Albericio, and G. Barany (1996) Preparation and application of xanthenylamide(XAL) handles for solid-phase synthesis of C-terminal peptide amides under particularly mild conditions. J. Org. Chem. 61: 6326-6339.
49. Bui, C. T., A. M. Bray, T. Nguyen, F. Ercole, and N. J. Maeji (2000) Solid phase synthesis of C-terminal peptide amides: development of a new aminoethyl-polystyrene linker on the Multipin solid support. J. Pept. Sci. 6: 243-250.
50. Kolhekar, A. S., R. E. Mains, and B. A. Eipper (1997) Peptidylglycine alpha-amidating monooxygenase: an ascorbate-requiring enzyme. Methods Enzymol. 279: 35-43.
51. Datamonitor (1998) Competing Successfully in Biotechnology: Future Opportunities in Therapeutic Proteins. Data-monitor Americas, NY, USA.
52. Wolfe, H. J. (1982) Calcitonin: Perspectives in current concepts. J. Endo. Inv. 5: 423-432.
53. Rittinghaus, E. F., R. D. Hesch, H. M. Harms, U. Busch, M. Prokop, and G. Delling (1990) The concept and treatment of osteoporosis. Exp. Gerontol. 25: 357-365.
54. Overgaard, K., D. Agnusdei, M. A. Hansen, E. Maioli, C. Christiansen, and C. Gennari (1991) Dose-response bioactivity and bioavailability of salmon calcitonin in premenopausal and postmenopausal women. J. Clin. Endocrinol. Metab. 72: 344-349.
55. Ohsuye, K., K. Kitano, S. Tanaka, H. Matsuo, and K. Mizuno (1998) Recombinant C-terminal alpha-amidating enzyme. US Patent 5,821,083.
56. Tamaoki, H. (1987) Preparation of peptides with C-terminal proline amide. US Patent 4,709,014.
57. Bertelsen, A. H., N. M. Mehta, G. A. Beaudry, J. P. Gilligan, and B. N. Jones (1998) Expression systems for amidating enzyme. US Patant 5,789,234.
58. Ogonowski, A. A., S. W. May, A. B. Moore, L. T. Barrett, C. L. O'Bryant, and S. H. Pollock (1997) Antiinflammatory and analgesic activity of an inhibitor of neuropeptide amidation. J. Pharmacol. Exp. Ther. 280: 846-853.