Stereocontrolled backbone connection of peptides by C = C-double bonds

Tetrahedron

Volumn 56, Issue 25, 2000, Pages 4187-4195

  Schumann, Susanne ^a   Zeitler, Kirsten ^a   Jäger, Martin ^a   Polborn, Kurt ^a   Steglich, Wolfgang ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Dimerisation; Olefins; Peptide analogues; Phosphines; Stereoselectivity

Indexed keywords

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL STRUCTURE; DIMERIZATION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0034674576     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00343-4     Document Type: Article

References (27)

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3. Jung, G. Angew. Chem. 1991, 103, 1067-1084; Angew. Chem., Int. Ed. Engl. 1991, 30, 1051-1068.
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5. (a) Lange, M.; Undheim, K. Tetrahedron 1998, 54, 5337-5344.
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7. © Efskind, J.; Benneche, T.; Undheim, K. Acta Chem. Scand. 1997, 103, 942-952.
8. (d) Rodbotten, S.; Benneche, T.; Undheim, K. Acta Chem. Scand. 1997, 51, 873-880.
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10. For the formation of non-olefinic amino acid dimers by coupling of two identical glycine units see: (a) Easton, C. J.; Peters, S. C. Aust. J. Chem. 1994, 47, 859-868.
11. (b) Alvarez-Ibarra, C.; Csaky, A. G.; Colmenero, B.; Quiroga, M. L. J. Org. Chem. 1997, 62, 2478-2482.
12. A backbone bridge towards the NH group of a tryptophan residue occurs in the cyclopeptide lyciumin A: Yahara, S.; Shigeyama, C.; Nohara, T.; Okuda, H.; Wakamatsu, K.; Yashuhara, T.; Tetrahedron Lett. 1989, 30, 6041-6042.
13. (a) Apitz, G.; Steglich, W. Tetrahedron Lett. 1991, 32, 3163-3166.
14. (b) Apitz, G.; Jäger, M.; Jaroch, S.; Kratzel, M.; Schäffeler, L.; Steglich, W. Tetrahedron 1993, 49, 8223-8232.
15. © Steglich, W.; Jäger, M.; Jaroch, S.; Zistler, P. Pure Appl. Chem. 1994, 66, 2167-2170.
16. Kober R., Steglich W. Liebigs Ann. Chem. 1983;599-609.
17. Schumann, S. Dissertation, Universität München, 1998.
18. 17 (b) Further details of the X-ray analyses (see also Ref. 16) are available on request from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK (deposit@ccdc.cam.ac.uk).
19. Details concerning the unusual NMR phenomena exhibited by the dimers 2 will be published elsewhere.
20. (a) Eliel, E. L. Stereochemistry of Carbon Compounds; McGraw-Hill: New York, 1962.
21. (b) Crombie, L. Q. Rev. Chem. Soc. 1952, 6, 101-104.
22. © Sonnet, P. E. Tetrahedron 1980, 36, 557-604.
23. In contrast, the amino acid dimers 2a and 2b are equilibrated with bases to yield mixtures of both diastereomers in a ratio of about 1:1 (Ref. 10).
24. -)-OMe; for details concerning deprotection and peptide coupling see Experimental.
25. 11b.
26. (a) Sheldrick, G. M. SHELXS 86; Universität Göttingen, 1986.
27. (b) Sheldrick, G. M. SHELXS 93; Universität Göttingen, 1993.