Stereocontrolled Synthesis of ψ[CH(CF3)NH]Gly-Peptides

Organic Letters

Volumn 5, Issue 21, 2003, Pages 3887-3890

  Molteni, Marco ^a   Volonterio, Alessandro ^a   Zanda, Matteo ^a  

^a POLITECNICO DI MILANO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3,3,3 TRIFLUORO 1 NITROPROPENE; BASE; PEPTIDE DERIVATIVE; PROPYLENE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; AZA MICHAEL ADDITION; CHEMICAL MODIFICATION; CHEMICAL REACTION; DIASTEREOISOMER; KINETICS; PROTEIN BINDING; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

MODELS, CHEMICAL; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; OLIGOPEPTIDES; STEREOISOMERISM;

EID: 0242460242     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0354730     Document Type: Article

References (21)

1. (a) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bös, M.; Cook, C. M. ; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039-3049.
2. (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720.
3. (c) Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305-341.
4. (d) Fletcher, M. D.; Campbell, M. M. Chem. Rev. 1998, 98, 763-795.
5. Loffet, A. J. Peptide Sci. 2002, 8, 1-7. ADMET is an acronym for absorption, distribution, metabolism, excretion, and toxicity.
6. (a) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015-2022.
7. (b) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232.
8. (c) Venkatraman, J.; Shankaramma, S. C.; Balaram, P. Chem. Rev. 2001, 101, 3131-3152.
9. (a) Volonterio, A.; Bravo, P.; Zanda, M. Org. Lett. 2000, 2, 1827-1830.
10. (b) Volonterio, A.; Bravo, P.; Zanda, M. Tetrahedron Lett. 2001, 42, 3141-3144.
11. (c) Volonterio, A. Bellosta, S.; Bravo, P.; Canavesi, M.; Corradi, E.; Meille, S. V.; Monetti, M.; Moussier, N.; Zanda, M. Eur. J. Org. Chem. 2002, 428-438.
12. (d) Volonterio, A.; Bellosta, S.; Bravin, F.; Bellucci, M. C.; Bruché, L.; Colombo, G.; Malpezzi, L.; Mazzini, S.; Meille, S. V.; Meli, M.; Ramírez de Arellano, C.; Zanda, M. Chem. Eur. J. 2003, in press. "Fluorine-effect" refers to the unique modification of chemical, physical, biophysiological, and pharmacological properties of fluorinated molecules brought about by fluorine atom(s).
13. For a review, see: Luzzio, F. A. Tetrahedron 2001, 57, 915-945.
14. Klenz, O.; Evers, R.; Miethchen, R.; Michalik, M. J. Fluorine Chem. 1997, 81, 205-210 and references therein.
15. For a review of asymmetric conjugate additions to nitroalkenes, see: Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698 and references therein.
16. 4. The crude was purified by FC (hexane/diisopropyl ether 9:1) affording 232 mg (79%) of the two diastereoisomers 4a and 5a in an 11.0:1 ratio.
17. Sani, M.; Bruché, L.; Chiva, G.; Fustero, S.; Piera, J.; Volonterio, A.; Zanda, M. Angew. Chem., Int. Ed. 2003, 42, 2060-2063. However, it should be stressed that the two processes are conceptually and mechanistically unrelated, since the stereocontrol of the reaction described in the reference above arose from an enolate protonation following the aza-Michael reaction, that per se was not stereogenic.
18. In the experiment of entry 9, DIPEA was not added at all, whereas in entry 10 (1.0 equiv added), it is completely neutralized as hydrochloric acid salt.
19. Catalytic effect of amine bases in Michael-type reactions is well-known. See for example: (a) McDaid, P.; Chen, Y.; Deng, L. Angew. Chem. Int. Ed. 2002, 41, 338-340 and references therein. (b) van Axel Castelli, V.; Dalla Cort, A.; Mandolini, L.; Reinhoudt, D. N.; Schiaffino, L. Eur. J. Org. Chem. 2003, 627-633.
20. Catalytic effect of amine bases in Michael-type reactions is well-known. See for example: (a) McDaid, P.; Chen, Y.; Deng, L. Angew. Chem. Int. Ed. 2002, 41, 338-340 and references therein. (b) van Axel Castelli, V.; Dalla Cort, A.; Mandolini, L.; Reinhoudt, D. N.; Schiaffino, L. Eur. J. Org. Chem. 2003, 627-633.
21. Full X-ray data and criteria for the stereochemistry assignments will be published in a full paper.