Synthesis of orthogonally protected bis(aminomethyl)malonic acid, and its use as a key building block in the preparation of cyclic peptide conjugates of 2-N-alkyl-1,2,3,4-tetrahydroisoquinoline on a solid support

European Journal of Organic Chemistry

Volumn , Issue 18, 2001, Pages 3467-3473

  Virta, Pasi ^a   Rosenberg, Jaana ^a   Karskela, Tuomas ^a   Heinonen, Petri ^a   Lönnberg, Harri ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

Amino acids; Cyclic peptides; Peptide conjugates; Solid phase synthesis

Indexed keywords

BIS(AMINOMETHYL)MALONIC ACID; CYCLOPEPTIDE; MALONIC ACID DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034801776     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200109)2001:18<3467::AID-EJOC3467>3.0.CO;2-A     Document Type: Article

References (30)

1. [1a] V. J. Hruby, F. Al-Obeidi, W. Kazmierski, Biochem. J. 1990, 268, 249-262 (review).
2. [1b] J. Rizo, L. M. Gierasch, Annu. Rev. Biochem. 1992, 61, 387-418 (review).
3. [1c] A. Geyer, G. Müller, H. Kessler, J. Am. Chem. Soc. 1994, 116, 7735-7743.
4. [1d] M. Pfaff, K. Tangemann, B. Müller, M. Gurrath, G. Müller, H. Kessler, R. Timpl, J. Engel, J. Biol. Chem. 1994, 209, 20233-20238.
5. [1e] C. Blackburn, S. A. Kates, Methods Enzymol 1997, 289, 175-198.
6. [1f] V. Hruby, H. Bartosz-Bechowski, P. Davis, J. Slaninova, T. Zalevska, D. Stropova, F. Porreca, H. I. Yamamura, J. Med. Chem. 1997, 40, 3957-3962.
7. [1g] X. Hu, A. S. C. Chan, X. Han, J. He, J.-P. Cheng, Tetrahedron Lett. 1999, 40, 7115-7118.
8. [2a] P. Heinonen, P. Virta, H. Lönnberg, Tetrahedron 1999, 55, 7613-7624.
9. [2b] P. Heinonen, J. Rosenberg, H. Lönnberg, Eur. J. Org. Chem. 2000, 3647-3652.
10. P. Heinonen, H. Lönnberg, Tetrahedron Lett. 1997, 38, 8569-8572.
11. C. H. Issidorides, R. Gulen, Org. Synth. 1963, IV, 679.
12. O. Mitsunobu, M. Yamada, T. Mukaiyama, Bull. Chem. Soc. Jpn. 1967, 40, 935-939.
13. [6a] K. Sato, T. Igarashi, Y. Yanagisawa, N. Kawauchi, H. Hashimoto, J. Yoshimura, Chem. Lett. 1988, 10, 1699.
14. [6b] M. Adinolfi, G. Barone, L. Guariniello, A. Iadonisi, Tetrahedron Lett. 1999, 40, 8439-8441.
15. E. J. Corey, G. Schmidt, Tetrahedron Lett. 1979, 399-402.
16. J. L. Wahlström, R. C. Ronald, J. Org. Chem. 1998, 63, 6021-6022.
17. [9a] A. F. Casy, J. L. Myers, J. Chem. Soc. 1964, 4639-4640.
18. [9b] J. March, Advanced Organic Chemistry. Reactions, Mechanisms, and structure, 4 th ed., J. Wiley & Sons, New York 1992, 935-937.
19. [9c] A. Guzaev, H. Salo, A. Azhayev, H. Lönnberg, Bioconjugate Chem. 1996, 7, 240-248.
20. [10a] A. Trzeciak, W. Bannwarth, Tetrahedron Lett. 1992, 33, 4557-4560.
21. [10b] S. A. Kates, N. A. Sole, C. R. Johnson, D. Hudson, G. Barany, F. Albericio, Tetrahedron Lett. 1993, 34, 1549-1552.
22. [10c] K. J. Jensen, J. Alsina, M. F. Songster, J. Vagner, F. Albericio, G. Barany, J. Am. Chem. Soc. 1998, 120, 5441-5452.
23. [10d] G. T. Bourne, W. D. F. Meutermans, P. F. Alewood, R. P. McGeary, M. Scanlon, A. A. Watson, M. L. Smyth,e J. Org. Chem. 1999, 64, 3095-3101.
24. [10e] J. Alsina, K. J. Jensen, F. Albericio, G. Barany, Chem. Eur. J. 1999, 5, 2787-2795.
25. [11a] L. A. Carpino, J. Am. Chem. Soc. 1993, 115, 4397-4398.
26. [11b] L. A. Carpino, A. El-Faham, C. A. Minor, F. Albericio, J. Chem. Soc., Chem. Commun. 1994, 201-203.
27. [12a] J. DiMaio, T. M.-D. Ngyen, C. Lemieux, P. W. Schiller, J. Med. Chem. 1982, 25, 1432-1438.
28. [12a] A. Ehrlich, H.-U. Heyne, R. Winter, M. Beyermann, H. Haber, L. A. Carpino, M. Bienert, J. Org. Chem. 1996, 61, 8831-8838.
29. [12c] J. Klose, M. Bienert, C. Mollenkopf, D. Wehle, C. Zhang, L. A. Carpino, P. Henklein, Chem. Commun. 1999, 1847-1848
30. [12d] W. D. F. Meutermans, S. W. Golding, G. T. Bourne, L. P. Miranda, M. J. Dooley, P. F. Alewood, M. L. Smythe, J. Am. Chem. Soc. 1999, 121, 9790-9796.