Design and synthesis of a novel water-soluble Aβ1-42 isopeptide: An efficient strategy for the preparation of Alzheimer's disease-related peptide, Aβ1-42, via O-N intramolecular acyl migration reaction

Tetrahedron Letters

Volumn 45, Issue 31, 2004, Pages 5965-5968

  Sohma, Youhei ^a   Sasaki, Masato ^a   Hayashi, Yoshio ^a   Kimura, Tooru ^a   Kiso, Yoshiaki ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

26 O acyl isoA 1 42; A 1 42; Alzheimer's disease; Difficult sequence; O N intramolecular acyl migration reaction; Water soluble A 1 42 isopeptide

Indexed keywords

AMYLOID BETA PROTEIN[1-42]; PEPTIDE DERIVATIVE; WATER;

ALZHEIMER DISEASE; ARTICLE; DRUG DESIGN; DRUG MECHANISM; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; PHYSIOLOGY;

EID: 3142752008     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.059     Document Type: Article

References (27)

1. Selkoe D.J. Nature. 399:1999;A23-31
2. Geula C., Wu C.K., Saroff D., Lorenzo A., Yuan M.L., Yankner B.A. Nat. Med. 4:1998;827-831
3. Sinha S., Lieberburg I. Proc. Natl. Acad. Sci. U.S.A. 96:1999;11049-11053
4. For examples: Younkin S.G. Ann. Neurol. 37:1995;287-288
5. Dahlgren K.N., Manelli A.M., Stine W.B. Jr., Baker L.K., Krafft G.A., LaDu M.J. J. Biol. Chem. 277:2002;32046-32053
6. Bitan G., Tarus B., Vollers S.S., Lashuel H.A., Condron M.M., Straub J.E., Teplow D.B. J. Am. Chem. Soc. 125:2003;15359-15365
7. Hou L., Shao H., Zhang Y., Li H., Menon N.K., Neuhaus E.B., Brewer J.M., Byeon I.-J.L., Ray D.G., Vitek M.P., Iwashita T., Makula R.A., Przybyla A.B., Zagorski M.G. J. Am. Chem. Soc. 126:2004;1992-2005
8. For examples: Burdick D., Soreghan B., Kwon M., Kosmoski J., Knauer M., Henschen A., Yates J., Cotman C., Glabe C. J. Biol. Chem. 267:1992;546-554
9. Quibell M., Turnell W.G., Johnson T. J. Chem. Soc., Perkin Trans. 1. 6:1995;2019-2024
10. Shen C.-L., Murphy R.M. Biophys. J. 69:1995;640-651
11. Fukuda H., Shimizu T., Nakajima M., Mori H., Shirasawa T. Bioorg. Med. Chem. Lett. 9:1999;953-956
12. Milton S.C.F., Milton R.C.D., Kates S.A., Glabe C. Lett. Peptide Sci. 6:1999;151-156
13. Murakami K., Irie K., Morimoto A., Ohigashi H., Shindo M., Nagano M., Shimizu T., Shirasawa T. Biochem. Biophys. Res. Commun. 294:2002;5-10
14. For a review, see: Sheppard R. J. Peptide Sci. 9:2003;545-552
15. Stine W.B. Jr., Dahlgren K.N., Krafft G.A., Ladu M.J. J. Biol. Chem. 278:2003;11612-11622
16. Stewart J.M. Gross E., Meienhofer J. The Peptides. Vol. 3:1981;169-201 Academic, NY
17. Tamamura H., Kato T., Otaka A., Fujii N. Org. Biomol. Chem. 1:2003;2468-2473
18. Mouls L., Subra G., Enjalbal C., Martinez J., Aubagnac J.-L. Terahedron Lett. 45:2004;1173-1178
19. Sohma Y., Sasaki M., Hayashi Y., Kimura T., Kiso Y. Chem. Commun. 2004;124-125
20. Kimura T., Ohtake J., Nakata S., Enomoto H., Moriwaki H., Akaji K., Kiso Y. Peptide Chemistry 1994. Ohno M. 1995;157-160 Protein Rearch Foundation, Osaka
21. Oliyai R., Stella V.J. Bioorg. Med. Chem. Lett. 5:1995;2735-2740
22. Kiso Y., Kimura T., Ohtake J., Nakata S., Enomoto H., Moriwaki H., Nakatani M., Akaji K. Peptides: Chemistry, Structure and Biology. 1996;Mayflower Scientific, England. pp 157-159
23. Hamada Y., Ohtake J., Sohma Y., Kimura T., Hayashi Y., Kiso Y. Bioorg. Med. Chem. 10:2002;4155-4167
24. Hayashi Y., Skwarczynski M., Hamada Y., Sohma Y., Kimura T., Kiso Y. J. Med. Chem. 46:2003;3782-3784
25. Skwarczynski M., Sohma Y., Kimura M., Hayashi Y., Kimura T., Kiso Y. Bioorg. Med. Chem. Lett. 13:2003;4441-4444
26. found: 4515.26; HPLC analysis at 230 nm: purity was >96%
27. 3CN for 40 min, 230 nm) of synthesized 1 was identical to that of commercially available Aβ1-42 (Peptide Institute, Inc., Osaka, Japan)