Enantioselective synthesis of a phenylalanine library containing alkyl groups on the aromatic moiety: Confirmation of stereostructure by X-ray analysis

Chemical and Pharmaceutical Bulletin

Volumn 54, Issue 6, 2006, Pages 873-877

  Li, Tingyou ^a   Tsuda, Yuko ^a   Minoura, Katsuhiko ^b   In, Yasuko ^b   Ishida, Toshimasa ^b   Lazarus, Lawrence H ^c   Okada, Yoshio ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b OSAKA MEDICAL COLLEGE   (Japan)

^c NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

Author keywords

Asymmetrical hydrogenation; Enzymatic digestion; L configuration; Phenylalanine analogue; X ray analysis

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALKYL GROUP; CHLORIDE; ESTER DERIVATIVE; PHENYLALANINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROGENATION; SYNTHESIS; X RAY ANALYSIS;

ALKYLATION; CRYSTALLOGRAPHY, X-RAY; HYDROCARBONS, AROMATIC; MOLECULAR STRUCTURE; NANOSTRUCTURES; PARTICLE SIZE; PHENYLALANINE; STEREOISOMERISM; SUBSTRATE SPECIFICITY; X-RAYS;

EID: 33744761796     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.54.873     Document Type: Article

References (27)

1. Lazarus L. H., Bryant S. D., Cooper P. S., Guerrini R., Balboni G., Salvadori S., Drug Disc Today, 3, 284-294 (1998).
2. Bryant S. D., Jinsmaa Y., Salvadori S., Okada Y., Lazarus L. H., Biopolymers (Peptide Science), 71, 86-102 (2003).
3. Li T., Fujita Y., Tsuda Y., Miyazaki A., Ambo A., Sasaki Y., Jinsmaa Y., Bryant S. D., Lazarus L. H., Okada Y., J. Med. Chem., 48, 586-592 (2005).
4. Sasaki Y., Suto T., Ambo A., Ouchi H., Yamamoto Y., Chem. Pharm. Bull., 47, 1506-1509 (1999).
5. Okada Y., Fujita Y., Motoyama T., Tsuda Y., Yokoi T., Li T., Sasaki Y., Ambo A., Jinsmaa Y., Bryant S. D., Lazarus L. H., Bioorg. Med. Chem., 11, 1983-1994 (2003).
6. Guerrini R., Capasso A., Sorrentino L., Anacardio R., Bryant S. D., Lazarus L. H., Attila M., Salvadori S., Eur. J. Pharmacol., 302, 37-42 (1996).
7. Guerrini R., Capasso A., Marastoni M., Bryant S. D., Cooper P. S., Lazarus L. H., Temussi P. A., Salvadori S., Bioorg. Med. Chem., 6, 57-62 (1998).
8. Sasaki Y., Hirabuki M., Ambo A., Ouchi H., Yamamoto Y., Bioorg. Med. Chem. Lett., 11, 327-329 (2001).
9. Ambo A., Murase H., Niizuma H., Ouchi H., Yamamoto Y., Sasaki Y., Bioorg. Med. Chem. Lett., 12, 879-881 (2002).
10. Ambo A., Niizuma H., Sasaki A., Kohara H., Sasaki Y., Bioorg. Med. Chem. Lett., 13, 1269-1272 (2003).
11. Sasaki Y., Sasaki A., Niizuma H., Goto H., Ambo A., Bioorg. Med. Chem., 11, 675-678 (2003).
12. Sasaki Y., Sasaki A., Ariizuma T., Igari Y., Sato K., Kohara H., Niizuma H., Ambo A., Biol. Pharm. Bull., 27, 244-247 (2004).
13. Porter J., Dykert J., Rivier J., Int. J. Peptide Protein Res., 30, 13-21 (1987).
14. Soloshonok V. A., Tang X., Hruby V. J., Tetrahedron, 57, 6375-6382 (2001).
15. Ooi T., Kameda M., Maruoka K., J. Am. Chem. Soc., 125, 5139-5151 (2003).
16. Ouchi H., Kumagai M., Sakurada S., Takahata H., Heterocycles, 64, 505-514 (2004).
17. Sagan S., Josien H., Karoyan P., Brunissen A., Chassaing G., Lavielle S., Bioorg. Med. Chem., 4, 2167-2178 (1996).
18. Nestor J. J., Ho T. L., Simpson R. A., Horner B. L., Jones G. H., McRae G. I., Vickery B. H., J. Med. Chem., 25, 795-801 (1982).
19. Dygos J. H., Yonan E. E., Scaros M. G., Goodmonson O. J., Getman D. P., Periana R. A., Beck G. R., Synthesis, 1992, 741-743 (1992).
20. CH of 2f cannot be determined.
21. Patel B. A., Ziegler C. B., Cortese N. A., Plevyak J. E., Zebovitz T. C., Terpko M., Heck R. F., J. Org. Chem., 42, 3903-3907 (1977).
22. Toth G., Lebl M., Hruby V. J., J. Chromatogr., 504, 450-455 (1990).
23. Vineyard B. D., Knowles W. S., Sabacky M. J., Bachman G. L., Weinkauff D. J., J. Am. Chem. Soc., 99, 5946-5952 (1977).
24. Taudien S., Schinkowski K., Krause H.-W., Tetrahedron: Asymmetry, 4, 73-84 (1993).
25. Sheldrick G. M., 'SHELXS97. Program for the Solution of Crystal Structure,' University of Gottingen, Germany, 1997.
26. Hahn T. (ed.), "International Tables for X-Ray Crystallography, " Vol. C, Kluwer Academic Publishers, Dordrecht, 1992.
27. Sheldrick G. M., 'SHELXL97. Program for the Refinement of Crystal Structure,' University of Gottingen, Germany, 1997.