Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B

Tetrahedron

Volumn 63, Issue 38, 2007, Pages 9502-9513

  Konno, Hiroyuki ^a   Kubo, Kanako ^b   Makabe, Hidefumi ^b   Toshiro, Emi ^c   Hinoda, Naoyuki ^c   Nosaka, Kazuto ^a   Akaji, Kenichi ^a  

^a KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

^c UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Aziridine; Cathepsin B; Cysteine protease inhibitor; Miraziridine A; Vinylogous arginine

Indexed keywords

ARGININE; AZIRIDINE; CATHEPSIN B; MIRAZIRIDINE A; PENTAPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; SOLID PHASE EXTRACTION; SPONGE (PORIFERA);

EID: 34547563523     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.06.082     Document Type: Article

References (26)

1. Nakao Y., Fujita M., Warabi K., Matsunaga S., and Fusetani N. J. Am. Chem. Soc. 122 (2000) 10462-10463
2. Schaschke N. Bioorg. Med. Chem. Lett. 14 (2004) 855-857
3. Vicik R., Busemann M., Baumann K., and Schirmeister T. Curr. Top. Med. Chem. 6 (2006) 331-353
4. Powers J.C., Asgian J.L., Ekici O.D., and James K.E. Chem. Rev. 102 (2002) 4639-4750
5. Otto H.-H., and Schirmeister T. Chem. Rev. 97 (1997) 133-171
6. Mladenovic M., Schirmeister T., Theil S., Theil W., and Enquls B. ChemMedChem 2 (2007) 120-128
7. Vicik R., Busemann M., Gelhaus C., Stiefl N., Scheiber J., Schmilz W., Schulz F., Mladenovic M., Engels B., Leippe M., Baumann K., and Schirmeister T. ChemMedChem 1 (2006) 1126-1141
8. Vicik R., Helten H., Schirmeister T., and Engels B. ChemMedChem 1 (2006) 1021-1028
9. Lyle, F. R. U.S. Patent 5,973,257, 1985;
10. Chem. Abstr. 65 (1985) 2870
11. Mori K., and Iwasawa H. Tetrahedron 36 (1980) 87-90
12. Legters J., Thijs L., and Zwanenburg B. Tetrahedron 47 (1991) 5287-5294
13. Thoen J.C., Morales-Ramos A.I., and Lipton M. Org. Lett. 12 (2002) 4455-4458
14. Bernatowicz S.M., Wu Y., and Matsueda R.G. Tetrahedron Lett. 34 (1993) 3389-3392
15. Wu Y., Matsueda R.G., and Bernatowicz Z.M. Synth. Commun. 23 (1993) 3055-3058
16. Konno H., Toshiro E., and Hinoda N. Synthesis (2003) 2161-2164
17. Maibaum J., and Rich D.H. J. Org. Chem. 53 (1988) 869-873
18. Harris B.D., and Joullié M.M. Tetrahedron 44 (1988) 3489-3500
19. Ninomiya K., Shioiri T., and Yamada S. Chem. Pharm. Bull. 22 (1974) 1398-1404
20. Bollhagen R., Schmiedberger M., Barlos K., and Grell E. J. Chem. Soc., Chem. Commun. (1994) 2559-2560
21. Carpino L.A., Imazumi H., El-Faham A., Ferrer F.J., Zhang C., Lee Y., Foxman B.M., Henklein P., Hanay C., Mügge C., Wenschuh H., Klose J., Beyerman M., and Bienert M. Angew. Chem., Int. Ed. 41 (2002) 441-445
22. Carpino L.A. J. Am. Chem. Soc. 115 (1993) 4397-4398
23. Hiwasa T., Fujita-Yoshigaki J., Shirouzu M., Koide H., Sawada T., Sakiyama S., and Yokoyama S. Cancer Lett. 69 (1993) 161-165
24. Barrett A.J., and Kirschke H. Methods Enzymol. 380 (1981) 535-561
25. Dixon M., and Webb E.C. Enzymes. 3rd ed. (1979), Longman, London pp 332-380
26. Yamamoto A., Tomoo K., Hara T., Murata M., Kitamura K., and Ishida T. J. Biochem. 127 (2000) 635-643