Direct solid-phase synthesis of quinoxaline-containing peptides

Tetrahedron Letters

Volumn 46, Issue 33, 2005, Pages 5525-5528

  Staszewska, Anna ^a   Stefanowicz, Piotr ^a   Szewczuk, Zbigniew ^a  

^a UNIVERSITY OF WROC AW   (Poland)

Author keywords

4 Amino 3 nitrophenylalanine; Quinoxaline; Solid phase peptide synthesis; Unnatural amino acids

Indexed keywords

1,2 DICARBONYL DERIVATIVE; ALANINE DERIVATIVE; BETA (3,4 DIAMINOPHENYL)ALANINE; PEPTIDE DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; METHODOLOGY; POLYMERIZATION; SOLID PHASE SYNTHESIS;

EID: 22144448620     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.047     Document Type: Article

References (32)

1. L. Wang, and P.G. Schultz Chem. Commun. 2002 1 11
2. A.F. Parsons Tetrahedron 52 1996 4149 4174
3. R.O. Duthaler Tetrahedron 50 1994 1539 1650
4. R.D. Anderson, J. Zhou, and S.M. Hecht J. Am. Chem. Soc. 124 2002 9674 9675
5. W.L. Scott, M.J. O'Donnell, F. Delgado, and J. Alsina J. Org. Chem. 67 2002 2960 2969
6. R.M. Adlington, J.E. Baldwin, D. Catterick, and G.J. Pritchard J. Chem. Soc., Perkin Trans. 1 1999 855 866 and references cited thererin
7. R.M. Adlington, J.E. Baldwin, D. Catterick, and G.J. Pritchard Chem. Commun. 1997 1757 1758
8. D.A. Dougherty Curr. Opin. Chem. Biol. 4 2000 645 652
9. For reviews, see: V.W. Cornish, D. Mendel, and P.G. Schultz Angew. Chem., Int. Ed. Engl. 34 1995 621 633
10. C.J. Noren, S.J. Anthony-Cahill, M.C. Griffith, and P.G. Schultz Science 244 1989 182 188
11. N. Voyer, and J. Larnothe Tetrahedron 51 1995 9241 9284
12. A. Jaso, B. Zarranz, I. Aldana, and A. Monge J. Med. Chem. 48 2005 2019 2025
13. H.U. Gali-Muhtasib, M. Diab-Assaf, and M.J. Haddadin Cancer Chemoth. Pharm. 55 2005 369 378
14. C. Perez-Melero, A.B.S. Maya, B. del Rey, R. Palaez, E. Caballero, and M. Medarde Bioorg. Med. Chem. Lett. 14 2004 3771 3774
15. G. Aguirre, H. Cerecetto, R. Di Maio, M. Gonzales, M.E.M.A. Alfaro, A. Jaso, B. Zarranz, M.A. Ortega, I. Aldana, and A. Monge-Vega Bioorg. Med. Chem. Lett. 14 2004 3835 3839
16. K. Toshima, T. Ozawa, T. Kimura, and S. Matsumara Bioorg. Med. Chem. Lett. 14 2004 2777 2779
17. B.K. Santra, P.A.N. Reddy, G. Neelakanta, S. Mahadevan, M. Nethaji, and A.R. Chakravarty J. Inorg. Biochem. 89 2002 191 196
18. A.M. Thomas, M. Nethaji, S. Mahadevan, and A.R. Chakravarty J. Inorg. Biochem. 94 2003 171 178
19. J.-Z. Wu, Z.-G. Xu, Y. Li, W.-G. Zhang, H.-P. Zeng, X. Xu, and Z.-Z. Zhou J. Chem. Crystallogr. 32 2002 75 80
20. Z. Zhao, D.D. Wisnoski, S.E. Wolkenberg, W.H. Leister, Y. Wang, and C.W. Lindsley Tetrahedron Lett. 45 2004 4873 4876
21. H.H. Wasserman, Y.O. Long, and J. Parr Tetrahedron Lett. 44 2003 361 363
22. X. Huang, and E.C.H. Long Bioorg. Med. Chem. Lett. 5 1995 1937 1940
23. S. Kotha, E. Brahmachary, A. Kuki, K. Lang, D. Anglos, B. Singaram, and W. Chrisman Tetrahedron Lett. 38 1997 9031 9034
24. A. El-Faham, A.M. El Massry, A. Amer, and Y.M. Gohar Lett. Pept. Sci. 9 2002 49 54
25. A.R. Brown, P.H.H. Hermkens, H.C.J. Ottenheijm, and D.C. Rees Synlett 1998 817 827
26. S. Bräse, C. Gil, and K. Knepper Bioorg. Med. Chem. 10 2002 2415 2437
27. Z. Wu, and N.J. Ede Tetrahedron Lett. 42 2001 8115 8118
28. G.B. Fields Methods in Enzymology: Solid-Phase Peptide Synthesis Vol. 289 1997 Academic Press New York pp 63-64
29. +); HPLC: C18 column Vydac: solv. A water + 0.1% TFA, solv. B acetonitrile + 0.1% TFA; gradient 0-100% B in A over 60 min.
30. Crystallographic data for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary data no. CCDC 269209. Copies of the data can be obtained free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk.]
31. E. Atherton, and R.C. Scheppart Solid Phase Peptide Synthesis 1989 IRL Press Oxford, New York, Tokyo p 12
32. W. Paw, and R. Eisenberg Inorg. Chem. 36 1997 2287 2293