Synthesis of amyloid β peptide 1-42 (E22Δ) click peptide: pH-triggered in situ production of its native form

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 14, 2009, Pages 4881-4887

  Wang, Hui ^a   Kakizawa, Taeko ^a   Taniguchi, Atsuhiko ^a   Mizuguchi, Takaaki ^a   Kimura, Tooru ^a   Kiso, Yoshiaki ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Alzheimer's disease; Amyloid peptide 1 42 (E22 ); Click peptide; O Acyl isopeptide method

Indexed keywords

AMYLOID BETA PROTEIN[1-42]; MUTANT PROTEIN;

ALZHEIMER DISEASE; ARTICLE; BETA SHEET; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; PH; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; STRUCTURE ANALYSIS;

ALZHEIMER DISEASE; AMINO ACID SEQUENCE; AMYLOID BETA-PROTEIN; CIRCULAR DICHROISM; HUMANS; HYDROGEN-ION CONCENTRATION; MOLECULAR SEQUENCE DATA; MUTATION; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; SOLUBILITY; WATER;

EID: 67650081408     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.06.017     Document Type: Article

References (56)

1. Hardy J., and Selkoe D.J. Science 297 (2002) 353
2. Haass C., Schlossmacher M.G., Hung A.Y., Vigo-Pelfrey C., Mellon A., Ostaszewski B.L., Lieberburg I., Koo E.H., Schenk D., Teplow D.B., and Selkoe D.J. Nature 359 (1992) 322
3. Seubert P., Vigo-Pelfrey C., Esch F., Lee M., Dovey H., Davis D., Sinha S., Schlossmacher M., Whaley J., Swindlehurst C., McCormack R., Wolfert R., Selkoe D., Lieberburg I., and Schenk D. Nature 359 (1992) 325
4. Shoji M., Golde T.E., Ghiso J., Cheung T.T., Estus S., Shaffer L.M., Cai C.X., McKay D.M., Tintner R., Frangione B., and Younkin S.G. Science 258 (1992) 126
5. Hendriks L., van Duijn C.M., Cras P., Cruts M., Van Hul W., van Harskamp F., Warren A., McInnis M.G., Antonarakis S.E., Martin J.J., Hofman A., and Van Broeckhoven C. Nat. Genet. 1 (1992) 218
6. Kamino K., Orr H.T., Payami H., Wijsman E.M., Alonso M.E., Pulst S.M., Anderson L., O'dahl S., Nemens E., White J.A., Sadovnick A.D., Ball M.J., Kaye J., Warren A., Mclnnis M., Antonarakis S.E., Korenberg J.R., Sharma V., Kukull W., Larson E., Heston L.L., Martin G.M., Bird T.D., and Schellenberg G.D. Am. J. Hum. Genet. 51 (1992) 998
7. Nilsberth C., Westlind-Danielsson A., Eckman C.B., Condron M.M., Axelman K., Forsell C., Stenh C., Luthman J., Teplow D.B., Younkin S.G., Naslund J., and Lannfelt L. Nat. Neurosci. 4 (2001) 887
8. Levy E., Carman M.D., Fernandez-Madrid I.J., Power M.D., Lieberburg I., van Duinen S.G., Bots G.T., Luyendijk W., and Frangione B. Science 248 (1990) 1124
9. Tagliavini F., Rossi G., Padovani A., Magoni M., Andora G., Sgarzi M., Bizzi A., Savoiardo M., Carella F., Morbin M., Giaccone G., and Bugiani O. Alzheimers Rep. 2 (1999) S28
10. Grabowski T.J., Cho H.S., Vonsattel J.P., Rebeck G.W., and Greenberg S.M. Ann. Neurol. 49 (2001) 697
11. Wakutani Y., Watanabe K., Adachi Y., Wada-Isoe K., Urakami K., Ninomiya H., Saido T.C., Hashimoto T., Iwatsubo T., and Nakashima K. J. Neurol. Neurosurg. Psychiat. 75 (2004) 1039
12. Tomiyama T., Nagata T., Shimada H., Teraoka R., Fukushima A., Kanemitsu H., Takuma H., Kuwano R., Imagawa M., Ataka S., Wada Y., Yoshioka E., Nishizaki T., Watanabe Y., and Mori H. Ann. Neurol. 63 (2008) 377
13. Nishitsuji K., Tomiyama T., Ishibashi K., Ito K., Teraoka R., Lambert M.P., Klein W.L., and Mori H. Am. J. Pathol. 174 (2009) 957
14. Zagorski M.G., Yang J., Shao H., Ma K., Zeng H., and Hong A. Methods Enzymol. 309 (1999) 189
15. Teplow D.B. Methods Enzymol. 413 (2006) 20
16. Taniguchi A., Sohma Y., Kimura M., Okada T., Ikeda K., Hayashi Y., Kimura T., Hirota S., Matsuzaki K., and Kiso Y. J. Am. Chem. Soc. 128 (2006) 696
17. Taniguchi A., Skwarczynski M., Sohma Y., Okada T., Ikeda K., Prakash H., Mukai H., Hayashi Y., Kimura T., Hirota S., Matsuzaki K., and Kiso Y. ChemBioChem 9 (2008) 3055
18. Sohma Y., and Kiso Y. ChemBioChem 7 (2006) 1549
19. Sohma Y., Taniguchi A., Yoshiya T., Chiyomori Y., Fukao F., Nakamura S., Skwarczyski M., Okada T., Ikeda K., Hayashi Y., Kimura T., Hirota S., Matsuzaki K., and Kiso Y. J. Pept. Sci. 12 (2006) 823
20. Taniguchi A., Sohma Y., Hirayama Y., Mukai H., Kimura T., Hayashi Y., Matsuzaki K., and Kiso Y. ChemBioChem 10 (2009) 710
21. Kiso Y., Taniguchi A., and Sohma Y. Wiley Encyclopedia of Chemical Biology Vol. 1 (2009), Wiley, Hoboken 379-383
22. Sohma Y., Sasaki M., Ziora Z., Takahashi N., Kimura T., Hayashi Y., and Kiso Y. Peptides, Peptide Revolution: Genomics, Proteomics and Therapeutics (2003), Kluwer Academic, Netherlands 67-68
23. Sohma, Y.; Sasaki, M.; Hayashi, Y.; Kimura, T.; Kiso, Y. Chem. Commun. 2004, 124.
24. Sohma Y., Sasaki M., Hayashi Y., Kimura T., and Kiso Y. Tetrahedron Lett. 45 (2004) 5965
25. Sohma Y., Hayashi Y., Kimura M., Chiyomori Y., Taniguchi A., Sasaki M., Kimura T., and Kiso Y. J. Pept. Sci. 11 (2005) 441
26. Sohma Y., Chiyomori Y., Kimura M., Fukao F., Taniguchi A., Hayashi Y., Kimura T., and Kiso Y. Bioorg. Med. Chem. 13 (2005) 6167
27. Sohma Y., Yoshiya T., Taniguchi A., Kimura T., Hayashi Y., and Kiso Y. Biopolymers 88 (2007) 253
28. Sohma Y., Taniguchi A., Skwarczynski M., Yoshiya T., Fukao F., Kimura T., Hayashi Y., and Kiso Y. Tetrahedron Lett. 47 (2006) 3013
29. Yoshiya T., Taniguchi A., Sohma Y., Fukao F., Nakamura S., Abe N., Ito N., Skwarczynski M., Kimura T., Hayashi Y., and Kiso Y. Org. Biomol. Chem. 5 (2007) 1720
30. Taniguchi A., Yoshiya T., Abe N., Fukao F., Sohma Y., Kimura T., Hayashi Y., and Kiso Y. J. Pept. Sci. 13 (2007) 868
31. Yoshiya T., Sohma Y., Kimura T., Hayashi Y., and Kiso Y. Tetrahedron Lett. 47 (2006) 7905
32. Yoshiya T., Ito N., Kimura T., and Kiso Y. J. Pept. Sci. 14 (2008) 1203
33. Matsuzaki K., Okada T., Tsukuda M., Ikeda K., Sohma Y., Chiyomori Y., Taniguchi A., Nakamura S., Ito N., Hayashi Y., and Kiso Y. Biochem. Biophys. Res. Commun. 371 (2008) 777
34. Kiewitz S.D., Kakizawa T., Kiso Y., and Cabrele C. J. Pept. Sci. 14 (2008) 1209
35. Mutter M., Chandravarkar A., Boyat C., Lopez J., Santos S.D., Mandal B., Mimna R., Murat K., Patiny L., Saucède L., and Tuchscherer G. Angew. Chem., Int. Ed. 43 (2004) 4172
36. Santos S.D., Chandravarkar A., Mandal B., Mimna R., Murat K., Saucède L., Tella P., Tuchscherer G., and Mutter M. J. Am. Chem. Soc. 127 (2005) 11888
37. Saucède L., Santos S.D., Chandravarkar A., Mandal B., Mimna R., Murat K., Camus M.S., Bérard J., Grouzmann E., Adrian M., Dubochet J., Lopez J., Lashuel H., Tuchscherer G., and Mutter M. Chimia 60 (2006) 199
38. Tuchscherer G., Chandravarkar A., Camus M.S., Bérard J., Murat K., Schmid A., Mimna R., Lashuel H.A., and Mutter M. Biopolymers 88 (2007) 239
39. Mimna R., Camus M.S., Schmid A., Tuchscherer G., Lashuel H.A., and Mutter M. Angew. Chem., Int. Ed. 46 (2007) 2681
40. Camus M.-S., Santos S.D., Chandravarkar A., Mandal B., Schmid W.A., Tuchscherer G., Mutter M., and Lashuel H.A. ChemBioChem 9 (2008) 2104
41. Carpino L.A., Krause E., Sferdean C.D., Schuemann M., Fabian H., Bienert M., and Beyermann M. Tetrahedron Lett. 45 (2004) 7519
42. Coin I., Dölling R., Krause E., Bienert M., Beyermann M., Sferdean C.D., and Carpino L.A. J. Org. Chem. 71 (2006) 6171
43. Coin I., Beyermann M., and Bienert M. Nat. Protoc. 2 (2007) 3247
44. Coin I., Schmieder P., Bienert M., and Beyermann M. J. Pept. Sci. 14 (2008) 299
45. Hentschel J., Krause E., and Börner H.G. J. Am. Chem. Soc. 128 (2006) 7722
46. Hentschel J., and Börner H.G. J. Am. Chem. Soc. 128 (2006) 14142
47. Börner H.G. Macromol. Chem. Phys. 208 (2007) 124
48. Börner H.G., and Schlaad H. Soft Mat. 3 (2007) 394
49. Shigenaga A., Tsuji D., Nishioka N., Tsuda S., Itoh K., and Otaka A. ChemBioChem 8 (2007) 1929
50. Lécaillon J., Gilles P., Subra G., Martinez J., and Amblard M. Tetrahedron Lett. 49 (2008) 4674
51. Vila-Perelló M., Hori Y., Ribó M., and Muir T.W. Angew. Chem., Int. Ed. 47 (2008) 7764
52. Nepomniaschiy N., Grimminger V., Cohen A., DiGiovanni S., Lashuel H.A., and Brik A. Org. Lett. 10 (2008) 5243
53. After 6 h incubation of the buffered solution of 1 which was synthesized by the conventional method, a slight amount of precipitation was observed. In addition, we also performed the CD measurement of 1 in 0.1% aqueous TFA. However, satisfactorily reliable data was not obtained.
54. Stoll, V. S.; Blanchard, J. S. Methods Enzymol. 1990, 182, 24.
55. Kaiser E., Colescott R.L., Bossinger C.D., and Cook P.I. Anal. Biochem. 34 (1970) 595
56. Pace C.N., Vajdos F., Fee L., Grimsley G., and Gray T. Protein Sci. 4 (1995) 2411