Acanthoscurrin fragment 101-132: Total synthesis at 60°C of a novel difficult sequence

Biopolymers

Volumn 92, Issue 1, 2009, Pages 65-75

  Remuzgo, César ^a   Andrade, Gustavo F S ^a   Temperini, Márcia L A ^a   Miranda, M Terêsa M ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

2 hydroxy 4 methoxybenzyl group; Chaotropic salts; CLEAR amide resin; Glycine rich protein; Peptide; Raman spectroscopy

Indexed keywords

2-HYDROXY-4-METHOXYBENZYL GROUP; CHAOTROPIC SALTS; CLEAR AMIDE RESIN; GLYCINE-RICH PROTEIN; PEPTIDE;

AMIDES; AMINES; INFRARED DEVICES; RAMAN SCATTERING; RAMAN SPECTROSCOPY; SALTS; SPECTRUM ANALYSIS;

RESINS;

AMINO ACID SEQUENCE; ANIMALS; ANTI-BACTERIAL AGENTS; BENZHYDRYL COMPOUNDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; INSECT PROTEINS; MOLECULAR SEQUENCE DATA; PEPTIDE FRAGMENTS; SPECTRUM ANALYSIS, RAMAN; SPIDERS; TEMPERATURE;

ACANTHOSCURRIA GOMESIANA; ARANEAE;

EID: 60149097224     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.21110     Document Type: Article

References (59)

1. Sachetto-Martins, G.; Franco, L. O.; de Oliveira, D. E. Biochim Biophys Acta 2000, 1492, 1-14.
2. Ringli, C.; Keller, B.; Ryser, U. Cell Mol Life Sci 2001, 58, 1430-1441.
3. Mousavi, A.; Hotta, Y. Appl Biochem Biotech 2005, 120, 169-174.
4. Josè, M.; Puigdomènech, P. New Phytol 1993, 125, 259-282.
5. Cassab, G. I. Annu Rev Plant Physiol Plant Mol Biol 1998, 49, 281-309.
6. Condit, C.; Meaguer, R. B. Nature 1986, 323, 178-181.
7. Bergeron, D.; Boivin, R.; Baszczynski, C. L.; Bellemare, G. Plant Sci 1994, 96, 87-98.
8. Matsui, M.; Toyosama, I.; Fukuda, M. Biosci Biotechnol Biochem 1995, 59, 2231-2234.
9. Merrifield, R. B. J Am Chem Soc 1963, 85, 2149-2154.
10. Albericio, F. Curr Opin Chem Biol 2004, 8, 211-221.
11. Kent, S. B. H. Annu Rev Biochem 1988, 57, 959-989.
12. Rahman, S. A.; El-Kafrawy, A.; Hattaba, A.; Anwer, M. F. Amino Acids 2007, 33, 531-536.
13. Dhalluin, C.; Boutillon, C.; Tartar, A.; Lippens, G. J Am Chem Soc 1997, 119, 10494-10500.
14. Cilli, E. M.; Marchetto, R.; Schreier, S.; Nakaie, C. R. J Org Chem 1999, 64, 9118-9123.
15. Henkel, B.; Bayer, E. J Pept Sci 1998, 4, 461-470.
16. Larsen, B. D.; Christensen, D. H.; Holm, A.; Zillmer, R.; Nielsen, O. F. J Am Chem Soc 1993, 115, 6247-6253.
17. Ryttersgard, J.; Larsen, B. D.; Holm, A.; Christensen, D. H.; Nielsen, O. F. Spectrochim Acta 1997, 53, 91-98.
18. Hansen, C. L.; Hansen, P. R.; Callisen, T. H.; Bauer, R.; Nielsen, O. F. J Raman Spectrosc 2002, 33, 142-146.
19. Rahman, S. S.; Busby, D. J.; Lee, D. C. J Org Chem 1998, 63, 6196-6199.
20. Yan, B.; Gremlich, H. U.; Moss, S.; Coppola, G. M.; Sun, Q.; Liu, L. J Comb Chem 1999, 1, 46-54.
21. Fenniri, H.; Chun, S.; Terreau, O.; Bravo-Vasquez, J. P. J Comb Chem 2007, 22, 46-54.
22. Lorenzini D. M.; Silva, P. I.; Fogaca, A. C.; Bulet, P.; Daffre, S. Dev Comp Immunol 2003, 27, 781-791.
23. Remuzgo, C.; Andrade, G. F. S.; Temperini, M. L. A.; Daffre, S.; Miranda, M. T. M. In Understanding Biology Using Peptides, Proceedings of the 19th American Peptide Symposium; Blondelle, S. E., Ed., Springer: New York, 2006; pp 86-87.
24. Gisin, B. F. Anal Chim Acta 1972, 58, 248-249.
25. Varanda, L. M.; Miranda, M. T. M. J Pept Res 1997, 50, 102-108.
26. Souza, M. P; Tavares, M. F. M.; Miranda, M. T. M. Tetrahedron 2004, 60, 4671-4681.
27. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal Biochem 1970, 34, 595-598.
28. Kiyota, S.; Franzoni, L.; Nicastro, G.; Benedetti, A.; Oyama, S.; Viviani, W.; Gambarini, A. G.; Spisni, A.; Miranda, M. T. M. J Med Chem 2003, 46, 2325-2333.
29. Miranda, M. T. M.; Grey Craig, A.; Miller, C.; Liddle, R. A.; Rivier, J. E. J Protein Chem 1993, 12, 533-544.
30. Fukushima, Y. Polym Bull 2000, 45, 237-244.
31. Zahariev, S.; Guarnaccia, C.; Zanuttin, F.; Pintar, A.; Esposito, G.; Maravic, G.; Krust, B.; Hovanessian, A. G.; Pongor, S. J Pept Sci 2005, 11, 17-28.
32. Rivier, J.; Miranda, M. T. M. In Houben Weyl Methods of Organic chemistry, Synthesis of Peptides and Peptidomimetics v. E22a; Goodman, M., Felix, A.; Moroder, L.; Toniolo, C., Eds.; Georg Thieme Verlag: Stuttgart, Germany, 2004; pp 806-813.
33. Loffredo, C.; Assunção, N. A.; Miranda, M. T. M. In Peptides for Youth, Proceedings of the 20th American Peptide Symposium; Escher, E.; Lubell, W. D.; Del Valle, S., Eds.; American Peptide Society, in press.
34. Krimm, S.; Bandekar, J. Adv Protein Chem 1986, 38, 181-364.
35. Cilli, E. M.; Oliveira, E.; Marchetto, R.; Nakaie, C. R. J Org Chem 1996, 61, 8992-9000.
36. Machado, A.; Xavier, G. C.; Lima, G. H.; Miranda, A.; Miranda, M. T. M. In Peptide Revolution: Genomics, Proteomics and Therapeutics, Proceedings of the 18th American Peptide Symposium; Chorev, M.; Sawyer, T. K.; Eds.; Kluwer Academic Publisher: Massachusset, 2004; pp 192-193.
37. Thaler, A.; Seebach, D. Helv Chim Acta 1991, 74, 628-643.
38. Stewart, J. M.; Klis, W. A. In Innovation and Perspective in solid phase synthesis, Proceedings of the Third International Peptide Symposium; Epton, R. Ed.; Mayflower Worldwide: Birmingham, UK, 1990; pp 1-9.
39. Narita, M.; Honda, S.; Umeyama, H.; Oban, S. Bull Chem Soc Jpn 1988, 61, 281-284.
40. Yamashiro, D.; Blake, J.; Li, C. H. Tetrahedron Lett 1976, 18, 1469-1472.
41. Milton, S. C. F.; Milton, R. C. L. Int J Pept Protein Res 1990, 36, 193-196.
42. Zhang, L.; Goldammer, C.; Henkel, B.; Zuehl, F.; Panhaus, G.; Jung, G.; Bayer, E. In Innovation and Perspective in solid phase synthesis, Proceedings of the Third International Peptide Symposium; Epton, R. Ed.; Mayflower Worldwide: Birmingham, UK, 1990; pp 711-716.
43. Small, E. W.; Fanconi, B.; Peticolas, W. L. J Chem Phys 1970, 52, 4369-4379.
44. Milton, R. C. L.; Milton, S. C. F.; Adams, P. A. J Am Chem Soc 1990, 112, 6039-6046.
45. Abd El Rahman, S.; Anzinger, H.; Mutter, M. Biopolymers 1980, 19, 173-187.
46. Becker, H.; Lucas, H. W.; Maul, J.; Pillai, V. N. R.; Anzinger, H.; Mutter, M. Makromol Chem, Rapid Commun 1982, 3, 217-23.
47. Bayer, E.; Hemmasi, B.; Albert, K.; Rapp, W.; Dengler, M. In Peptides 1983, Proceedings of the 8th American Peptide Symposium; Hruby, V. J., Rich, D. H., Eds.; Pierce Chemical Company: Rockford, IL, 1983; pp 87-90.
48. Merrifield, B. In Peptides: Synthesis, Structures and Applications; Gutte, B., Ed.; Academic Press: San Diego, CA, 1995, pp 94-169.
49. Kempe, M.; Barany, G. J Am Chem Soc 1996, 118, 7083-7093.
50. García-Martin, F.; Quintanar-Audelo, M.; Garcia-Ramos, Y.; Cruz, L. J.; Gravel, C.; Furic, R.; Cote, S.; Tulla-Puche, J.; Albericio, F. J Comb Chem 2006, 8, 213-220.
51. Bodanszky, M.; Deshmane, S. S.; Martinez, J. J Org Chem 1979, 44, 1622-1625.
52. Blaakmeer, J.; Tijsse-Klasen, T.; Tesser, G. I. Int J Pept Protein Res 1991, 37, 556-564.
53. Johnson, T.; Quibell, M.; Owen, D.; Sheppard, R. C. J Chem Soc Chem Commun 1993, 4, 369-372.
54. Wöhr, T.; Wahl, F.; Nefzi, A.; Rohwedder, B.; Sato, T.; Sun, X.; Mutter, M. J Am Chem Soc 1996, 118, 9218-9227.
55. García-Martín, F.; White, P.; Steinauer, R.; Côté, S.; Tulla-Puche, J.; Albericio, F. Biopolymers 2006, 84, 566-575.
56. Quibell, M.; Turnell, W. G.; Johnson, T. Tetrahedron Lett 1994, 35, 2237-2238.
57. Simmonds R. G. Int J Pept Protein Res 1996, 47, 36-41.
58. Torreggiani, A., Fini, G. J. Raman Spectrosc 1998, 29, 229-236.
59. Drewes, J. A.; Rowlen, K. L. Biophys J 1993, 65, 985-991.