Solid-phase synthesis of linear and cyclic peptides containing a calix[4]arene amino acid

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3450-3453

  Baldini, Laura ^a   Sansone, Francesco ^a   Scaravelli, Federico ^a   Massera, Chiara ^b   Casnati, Alessandro ^a   Ungaro, Rocco ^a  

^a Dipartimento di Chimica Organica e Industriale   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CALIXARENE;

AMINO ACID COMPOSITION; ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATION; CYCLIZATION; ELECTROSPRAY MASS SPECTROMETRY; MOLECULAR INTERACTION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID PHASE SYNTHESIS;

EID: 65549155680     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.198     Document Type: Article

References (23)

1. Sansone F., Barboso S., Casnati A., Fabbi M., Pochini A., Ugozzoli F., and Ungaro R. Eur. J. Org. Chem. (1998) 897-905
2. Lazzarotto M., Sansone F., Baldini L., Casnati A., Cozzini P., and Ungaro R. Eur. J. Org. Chem. (2001) 595-602
3. Casnati A., Sansone F., and Ungaro R. Acc. Chem. Res. 36 (2003) 246-254
4. Baldini L., Casnati A., Sansone F., and Ungaro R. In: Vicens J., and Harrowfield J. (Eds). Calixarenes in the Nanoworld (2006), Springer, Netherlands 233-257
5. Sebti S.M., and Hamilton A.D. Oncogene 19 (2000) 6566-6573
6. Baldini L., Sansone F., Faimani G., Massera C., Casnati A., and Ungaro R. Eur. J. Org. Chem. (2008) 869-886
7. Huttunen-Hennelly H.E.K., and Sherman J.C. Org. Biomol. Chem. 5 (2007) 3637-3650
8. Goun E.A., Pillow T.H., Jones L.R., Rothbard J.B., and Wender P.A. ChemBioChem 7 (2006) 1497-1515
9. Solid-phase protocols for the synthesis of N- or C-linked peptidocalixarenes have been reported (Kubo, M.; Nashimotoa, E.; Tokiyoa, T.; Morisakia, Y.; Kodamaa, M.; Hioki, H. Tetrahedron Lett. 2006, 47, 1927-1931; Brewster, R. E.; Dalton, B. G. A.; Shuker, S. B. Bioorg. Chem. 2005, 33, 16-21), but differ from our approach since they are based on anchoring the calixarene scaffold to the resin followed by condensation of the amino acids.
10. +].
11. 2+].
12. Haubner R., Finsinger D., and Kessler H. Angew. Chem., Int. Ed. 36 (1997) 1374-1389
13. Pfaff M., Tangemann K., Müller B., Gurrath M., Müller G., Kessler H., Timpl R., and Engel J. J. Biol. Chem. 269 (1994) 20233-20238
14. Dechantsreiter M.A., Planker E., Mathä B., Lohof E., Hölzemann G., Jonczyk A., Goodman S.L., and Kessler H. J. Med. Chem. 42 (1999) 3033-3040
15. Lohof E., Planker E., Mang C., Burkhart F., Dechantsreiter M.A., Haubner R., Wester H.-J., Schwaiger M., Hölzemann G., Goodman S.L., and Kessler H. Angew. Chem., Int. Ed. 39 (2000) 2761-2764
16. Belvisi L., Bernardi A., Checchia A., Manzoni L., Potenza D., Scolastico C., Castorina M., Cupelli A., Giannini G., Carminati P., and Pisano C. Org. Lett. 3 (2001) 1001-1004
17. +]. Crystallographic data (excluding structure factors) for the structure of Fmoc-2 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-714083.
18. +]. The very poor solubility of 8 in aqueous and organic phases prevented its NMR characterization.
19. Babine R.E., and Bender S.L. Chem. Rev. 97 (1997) 1359-1472
20. Garner J., and Harding M.M. Org. Biomol. Chem. 5 (2007) 3577-3585
21. Kubik S. Chem. Soc. Rev. 38 (2009) 585-605
22. Lee C.C., Grenier C., Meijer E.E., and Schenning A.P.H.J. Chem. Soc. Rev. 38 (2009) 671-683
23. Tuchscherer G., and Mutter M. J. Biotechnol. 41 (1995) 197-210