Asymmetric synthesis of optically pure β-isopropylphenylalanine: A new β-branched unusual amino acid

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1563-1566

  Liao, Subo ^a   Hruby, Victor J ^a  

^a University of Arizona ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA ISOPROPYLPHENYLALANINE; PHENYLALANINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; X RAY DIFFRACTION;

EID: 0029970483     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00091-3     Document Type: Article

References (25)

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4. (c) Hruby, V. J.; Al-Obeidi, F. and Kazmierski, W. Biochem. J. 1990, 268, 249-262.
5. (a) Dharanipragada, R.; VanHulle, K.; Bannister, A.; Bear, S.; Kennedy, L. and Hruby, V. J. Tetrahedron 1992, 48, 4733-4748;
6. (b) Nicolas, E.; Russell, K. C.; Hruby, V. J. J. Org. Chem. 1993, 58, 766-770;
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9. (e) Li, G.; Patel, D. and Hruby, V. J. J. Chem. Soc. Perkin Trans. 1 1994, 3057-3059;
10. (f) Qian, X.; Russell, K. C.; Boteju, L. W. and Hruby, V. J. Tetrahedron 1995, 51, 1033-1054;
11. (g) Shapiro, G.; Buechler, D.; Marzi, M.; Schmidt, K. and Gomez-Lor, B. J. Org. Chem. 1995, 60, 4978-4979;
12. (h) Burk, M.; Gross, M. F. and Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375-9376.
13. (a) Qian, X.; Kövér K. E.; Shenderovich, M. D.; Lou, B-S.; Misicka, A.; Zalewska, T.; Horvàth, R.; Davis, P.; Bilsky, E. J.; Porreca, F.; Yamamura, H. I. and Hruby, V. J. J. Med. Chem. 1994, 37, 1746-1757;
14. (b) Nikiforovich, G. V.; Prakash, O. M.; Gehrig, C. A. and Hruby, V. J. Int. J. Peptide Protein Res. 1993, 41, 347-361;
15. (c) Huang, Z.; He, Y-B.; Raynor, K.; Tallent, M.; Reisine, T. and Goodman, M. J. Am. Chem. Soc. 1992, 9390-9401;
16. (d) Toth, G.; Russell, K. C.; Landis, G.; Kramer, T. H.; Fang, L.; Knapp, R.; Davis, P.; Burks, T. F.; Yamamura, H. I. and Hruby, V J. J. Med.Chem. 1992, 35, 2383-2391, and references therein.
17. Liao, S.; Shenderovich, M. and Hruby, V.J. unpublished results.
18. 3).
19. Evans, D. A. and Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761.
20. (a) Evans, D. A.; Ellman, J. A. and Dorow, R. L. Tetrahedron Lett. 1987, 28, 1123-1126;
21. (b) Evans, D. A.; Britton, T.; Ellman, J. and Dorow, R. J. Am. Chem. Soc. 1990, 112, 4011-4030.
22. 2O (4:1:1). The optical isomers of β-isopropylphenylalanine revealed single spots with Rf values of 0.55(2R,3S), 0.49(2R,3R), 0.74(2S,3R), 0.76(2S,2S);
23. 3);
24. Due to the relative small coupling constant values between the a proton and β proton in the products, qauntitative description of the biased conformation needs more studies. For related NMR method to describe the conformational properties of β-branched aminoacids, please see Kövër, E. K.; Jiao, D.; Fang, S. and Hruby, V.J. Magnetic Resonance In Chemistry 1993, 31, 1072-1076.
25. Liao, S.; Bruck, M. and Hruby, V.J. in preparation for publication.