Efficient synthesis of differentially protected (S,S)-2,7- diaminooctanedioic acid, the dicarba analogue of cystine

Helvetica Chimica Acta

Volumn 81, Issue 11, 1998, Pages 2053-2061

  Lange, Meinolf ^a,b   Fischer, Peter M ^a,c  

^a NYCOMED IMAGING AS   (Norway)

^b ARQULE INC   (United States)

^c CYCLACEL LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2,7 BIS{[(BENZYLOXY)CARBONYL]AMINO}OCTANEDIOIC ACID 2 OXO PHENYLETHYL ESTER; 2,7 DIAMINOSUBERIC ACID; CYSTEINE DERIVATIVE; CYSTINE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTALLIZATION; DIMERIZATION; DISULFIDE BOND; ENANTIOMER; ESTERIFICATION; GEL CHROMATOGRAPHY; HYDROLYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0031761510     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1522-2675(19981111)81:11<2053::AID-HLCA2053>3.0.CO;2-4     Document Type: Article

References (30)

1. P. K. Bhatnagar, E. K. Agner, D. Alberts, B. E. Arbo, J. F. Callahan, A. S. Cuthbertson, S. J. Engelsen, H. Fjerdingstad, M. Hartmann, D. Heerding, J. Hiebl, W. F. Huffman, M. Husben, A. G. King, P. Kremminger, C. Kwon, S. LoCastro, D. Løvhaug, L. Pelus, S. Petteway, J. S. Takata, J. Med. Chem. 1996, 39, 3814;
2. b) M. Lange, A. S. Cuthbertson, R. Towart, P. M. Fischer, J. Peptide Sci. 1998, 4, 289.
3. W. Treibs, H. Reinheckel, Chem. Ber. 1956, 89, 51.
4. J. P. Greenstein, M. Winitz, 'Chemistry of the Amino Acids', Robert E. Krieger Publishing Company, Malabar, FL, 1984, Vol. 3, p. 2501.
5. K. Mori, H. Kumagae, Nippon Kagaku Zasshi 1961, 82, 1372.
6. K. Mori, K. Kumagae, Nippon Kagaku Zasshi, 1961, 82, 1375.
7. J. Hiebl, M. Blanka, A. Guttman, H. Kollmann, K. Leitner, G. Mayrhofer, F. Rovenszky, K. Winkler, Tetrahedron 1998, 54, 2059.
8. R. M. Williams, C. Yuan, J. Org. Chem. 1992, 57, 6519; G. Bold, T. Allmendinger, P. Herold, L. Moesch, H. P. Schär, R. O. Duthaler, Helv. Chim. Acta 1992, 75, 865.
9. R. M. Williams, C. Yuan, J. Org. Chem. 1992, 57, 6519; G. Bold, T. Allmendinger, P. Herold, L. Moesch, H. P. Schär, R. O. Duthaler, Helv. Chim. Acta 1992, 75, 865.
10. U. Schöllkopf, Tetrahedron 1983, 39, 2085.
11. R. F. Nutt R. G. Strachan, D. F. Veber, F. W. Holly, J. Org. Chem. 1980, 45, 3078.
12. J. Hiebl, H. Kollmann, F. Rovenszky, K. Winkler, Bioorg. Med. Chem. Lett. 1997, 7, 2963.
13. A. R. Jurgens, Tetrahedron Lett. 1992, 33, 4727; R. C. Holcomb, S. Schow, S. Ayral-Kaloustian, D. Powell, ibid. 1994, 35, 7005; R. M. Williams, C. Yuan, J. Org. Chem. 1994, 59, 6190.
14. A. R. Jurgens, Tetrahedron Lett. 1992, 33, 4727; R. C. Holcomb, S. Schow, S. Ayral-Kaloustian, D. Powell, ibid. 1994, 35, 7005; R. M. Williams, C. Yuan, J. Org. Chem. 1994, 59, 6190.
15. A. R. Jurgens, Tetrahedron Lett. 1992, 33, 4727; R. C. Holcomb, S. Schow, S. Ayral-Kaloustian, D. Powell, ibid. 1994, 35, 7005; R. M. Williams, C. Yuan, J. Org. Chem. 1994, 59, 6190.
16. M. J. I. Andrews, A. B. Tabor, Tetrahedron Lett. 1997, 38, 3063.
17. D. Seebach, E. Dziadulewicz, L. Behrendt, S. Cantoreggi, R. Fitzi, Liebigs Ann. Chem. 1989, 1215.
18. J. Bouchaudon, G. Dutruc-Rosset, D. Farge, C. James, J. Chem. Soc., Perkin Trans. 1 1989, 695.
19. Y. Gao, P. Lane-Bell, J. Vederas, J. Org. Chem. 1998, 63, 2133; R. M. Williams, J. Liu, ibid. 1998, 63, 2130.
20. Y. Gao, P. Lane-Bell, J. Vederas, J. Org. Chem. 1998, 63, 2133; R. M. Williams, J. Liu, ibid. 1998, 63, 2130.
21. A. Arendt, A. Kolodziejczyk, T. Sokolowska, E. Szulfer, Rocz. Chem. 1976, 48, 1501.
22. U. Schöllkopf, R. Hinrichs, R. Lonsky, Angew. Chem. 1987, 99, 137.
23. P. M. Fischer, M. Solbakken, K. Undheim, Tetrahedron 1994, 50, 2277.
24. G. C. Stelakatos, A. Paganou, I. Zervas, J. Chem. Soc. (C) 1966, 1191.
25. M. Ueki, H. Aoki, T. Katoh, Tetrahedron Lett. 1993, 34, 2783.
26. H. Leuchs, Chem. Ber. 1906, 39, 857.
27. K. Poduska, H. Gross, Chem. Ber. 1961, 94, 527.
28. J. Martinez, J. C. Tolle, M. Bodanszky, J. Org. Chem. 1979, 44, 3596.
29. P. M. Fischer, J. Sandosham, Tetrahedron Lett. 1995, 36, 5409.
30. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923.