Synthesis of the repeating decapeptide unit of Mefp1 in orthogonally protected form

Journal of Organic Chemistry

Volumn 65, Issue 5, 2000, Pages 1414-1421

  Taylor, Carol M ^a   Weir, Claudette A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AMINO ACID DERIVATIVE; HYDROXYPROLINE; OLIGOPEPTIDE; PROTEIN MEFP1; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG;

ADHESION; ARTICLE; MUSSEL; PEPTIDE SYNTHESIS; PROTEIN POLYMERIZATION; PROTEIN STRUCTURE; REACTION ANALYSIS;

ADHESIVENESS; ADHESIVES; ANIMALS; BIVALVIA; HYDROXYPROLINE; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; OLIGOPEPTIDES; PEPTIDE FRAGMENTS; PROTEINS; REPETITIVE SEQUENCES, AMINO ACID;

EID: 0034629472     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991523w     Document Type: Article

References (55)

1. Waite, J. H.; Tanzer, M. L. Science 1981, 212, 1038-1040.
2. Waite, J. H.; Housley, T. J.; Tanzer, M. L. Biochemistry 1985, 24, 5010-5014.
3. Strausberg, R. L.; Link, R. P. TIBTECH 1990, 8, 53-57.
4. Green, K. Mussel Adhesive Proteins. In Surgical Adhesives and Sealants; Sierra, D. H., Saltz, R., Eds.; Technomic: Lancaster, 1997.
5. Olivieri, M. P.; Baier, R. E.; Loomis, R. E. Biomaterials 1992, 13, 1000-1008.
6. Deacon, M. P.; Davis, S. S.; Waite, J. H.; Harding, S. E. Biochemistry 1998, 37, 14108-14112.
7. Baty, A. M.; Leavitt, P. K.; Siedlecki, C. A.; Tyler, B. J.; Suci, P. A.; Marchant, R. E.; Geesey, G. G. Langmuir 1997, 131, 55702-5710.
8. Burzio, V. A.; Silva, T.; Pardo, J.; Burzio, L. O. Anal. Biochem. 1996, 241, 190-194.
9. Nagy, P. I.; Patel, H. C.; Dreyer, W.; Hopfinger, A. J. Int. J. Pept. Protein Res. 1991, 38, 84-89.
10. Olivieri, M. P.; Wollman, R. M.; Alderfer, J. L. J. Pept. Res. 1997, 50, 436-442.
11. Taylor, S. W.; Waite, J. H.; Ross, M. M.; Shabanowitz, J.; Hunt, D. F. J. Am. Chem. Soc. 1994, 116, 10803-10804.
12. The decapeptide 1 and related compounds are drawn in such a way as to depict the conformation in which all X-Pro peptide bonds adopt the trans orientation. We appreciate and find interesting the possibility that other conformations may be significant.
13. Sigma Catalogue, 1998, Sigma-Aldrich Chemical Co., p 62.
14. Yamamoto, H. Biotech. Genetic Eng. Rev. 1995, 13, 133-165.
15. Yamamoto, H.; Nagai, A. Marine Chem. 1992, 37, 131-143.
16. Yamamoto, H.; Ogawa, T.; Nishida, A. J. Colloid Interface Sci. 1995, 176, 105-110.
17. Yamamoto, H.; Ogawa, T.; Ohkawa, K. J. Colloid Interface Sci. 1995, 176, 111-116.
18. Yu, M.; Deming, T. J. Macromolecules 1998, 31, 4739-4745.
19. Yu, M.; Hwang, J.; Deming, T. J. J. Am. Chem. Soc. 1999, 121, 5825-5826.
20. Burzio, L. O.; Burzio, V. A.; Silva, T.; Burzio, L. A.; Pardo, J. Curr. Opin. Biotechnol. 1997, 8, 309-312.
21. Kamino, K.; Odo, S.; Maruyama, T. Biol. Bull. 1996, 190, 403-409.
22. Bradley, D. J.; Kjellbom, P.; Lamb, C. J. Cell 1992, 70, 21-30.
23. Swerdloff, M. D.; Anderson, S. B.; Sedgwick, R. D.; Gabriel, M. K.; Brambilla, R. J.; Hindenlang, D. M.; Williams, J. I Int. J. Pept. Protein Res. 1989, 33, 318-317.
24. Yamamoto, H. J. Chem. Soc., Perkin Trans. 1 1987, 613-618.
25. (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 55, 2149-2154.
26. (b) Merrified, R. B. Science 1986, 232, 341-347.
27. Angell, Y. M.; García-Echeverría, C.; Rich, D. H. Tetrahedron Lett. 1994, 35, 5981-5984.
28. (a) Carpino, L. A.; Han, G. Y. J. Org. Chem. 1972, 37, 3404-3490.
29. (b) Atherton, E.; Sheppard, R. C. In The Peptides; Udenfriend, S., Meienhofer, J., Eds.; Academic Press: Orlando, 1987; Vol. 9, pp 1-38.
30. Kunz, H.; Waldmann, H.; Unverzagt. C. Int. J. Pept. Protein Res. 1985, 26, 493.
31. In addition to ref 24, see the following papers for the incorporation of DOPA into small peptides: (a) Bai, J. P. F. Pharm. Res. 1995, 12, 1101-1104. (b) Nakonieczna, L.; Przychodzen, W.; Chimiak, A. Amino Acids 1995, 8, 109-112. (c) Yamamoto, Y.; Nagai, A.; Harushima, Y.; Senda, T. In Peptides 1992; Schneider, C. H., Eberle, A. N., Eds.; ESCOM Science Publishers: B.V., 1993; pp 165-166.
32. In addition to ref 24, see the following papers for the incorporation of DOPA into small peptides: (a) Bai, J. P. F. Pharm. Res. 1995, 12, 1101-1104. (b) Nakonieczna, L.; Przychodzen, W.; Chimiak, A. Amino Acids 1995, 8, 109-112. (c) Yamamoto, Y.; Nagai, A.; Harushima, Y.; Senda, T. In Peptides 1992; Schneider, C. H., Eberle, A. N., Eds.; ESCOM Science Publishers: B.V., 1993; pp 165-166.
33. In addition to ref 24, see the following papers for the incorporation of DOPA into small peptides: (a) Bai, J. P. F. Pharm. Res. 1995, 12, 1101-1104. (b) Nakonieczna, L.; Przychodzen, W.; Chimiak, A. Amino Acids 1995, 8, 109-112. (c) Yamamoto, Y.; Nagai, A.; Harushima, Y.; Senda, T. In Peptides 1992; Schneider, C. H., Eberle, A. N., Eds.; ESCOM Science Publishers: B.V., 1993; pp 165-166.
34. (a) Nakonieczna, L.; Przychodzen, W.; Chimiak, A. In Peptides 1992; Schneider, C. H., Eberle, A. N., Eds.; ESCOM Science Publishers: B. V., 1993; pp 194-195.
35. (b) Nakonieczna, L.; Przychodzen, W.; Chimiak, A. Liebigs Ann. Chem. 1994 1055-1058.
36. Fleet, G. W. J.; Son, J. C. Tetrahedron 1988, 44, 2637-2647.
37. Weir, C. A.; Taylor, C. M. J. Org. Chem. 1999, 64, 1554-1558.
38. Lear, J. D.; Schneider, J. P.; Kienker, P. K.; DeGrado, W. F. J. Am. Chem. Soc. 1997, 119, 3212-3217.
39. Colucci, W. J.; Tung, R. D.; Petri, J. A.; Rich, D. H. J. Org. Chem. 1990, 55, 2895-2903.
40. Le Nguyen, D.; Seyer, R.; Heitz, A.; Castro, B. J. Chem. Soc., Perkin Trans, 1 1985, 1025-1031.
41. Di Fenza, A.; Tancredi, M.; Galoppini, C.; Rovero, P. Tetrahedron Lett. 1998, 39, 8529-8532.
42. Wijkmans, J. C. H. M.; Kruijtzer, J. A. W.; van der Marel, G. A.; van Boom, J. H.; Bloemhoff, W. Recl. Trav. Chim. Pays-Bas 1994, 113, 394-397.
43. (a) Castro, B.; Dormoy, J. R. Bull. Soc. Chim. Fr. 1973, 3359-3361.
44. (b) Coste, J.; Dufour, M.-N.; Pantaloni, A.; Castro, B. Tetrahedron Lett. 1990, 31, 669-672.
45. (c) Coste, J.; Frérot, E.; Jouin, P. J. Org. Chem. 1994, 59, 2437-2446.
46. For a comprehensive review of difficult peptide coupling reactions see: Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243-2266.
47. (a) Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203-6205.
48. (b) Benoiton, N. L.; Kuroda, K.; Chen, F. M. F. Int. J. Pept. Protein Res. 1982, 20, 81-86.
49. Narita, M.; Fukunaga, T.; Wakabayashi, A.; Ishikawa, K.; Nakano, H. Int. J. Pept. Protein Res. 1984, 23, 306-314.
50. (a) Lloyd-Williams, P.; Albericio, F.; Giralt, E. Chemical Approaches to the Synthesis of Peptides and Proteins; CRC Press: Boca Raton, 1997; pp 148-153.
51. (b) Lloyd-Williams, P.; Albercio, F.; Giralt, E. Int. J. Pept. Protein Res. 1991, 37, 58-60.
52. (c) Gairí, M.; Lloyd-Williams, P.; Albercio, F.; Giralt, E. Int. J. Pept. Protein Res. 1995, 46, 119-133.
53. (a) Benz, H. Synthesis 1994, 337-358.
54. (b) Lloyd-Williams, P.; Albericio, F.; Giralt, E. Chemical Approaches to the Synthesis of Peptides and Proteins; CRC Press: Boca Raton, 1997; pp 139-148.
55. (c) Lloyd-Williams, P.; Albericio, F.; Giralt, E. Tetrahedron 1993, 49, 11065-11133.