An improved preparation of 4-hydroxymethyl-L-phenylalanine

Synthetic Communications

Volumn 28, Issue 22, 1998, Pages 4279-4285

  Morera, Enrico ^a   Ortar, Giorgio ^a   Varani, Aurelio ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYMETHYLPHENYLALANINE; PHENYLALANINE; UNCLASSIFIED DRUG;

ARTICLE; PROTEIN PHOSPHORYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS;

EID: 0031717267     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919809458709     Document Type: Article

References (28)

1. Groundwater, P. W., Solomons, K. R. H., Drewe, J. A., and Munawar, M. A. in "Progress in Medicinal Chemistry", Ellis, G. P. and Luscombe, D. K. Eds., Elsevier, Amsterdam, 1996, Vol 33, pp. 233-329. Fry, D. W. in "Annual Reports in Medicinal Chemistry", Bristol, J. A. Editor-in-Chief, Academic Press, San Diego, 1996, Vol 31, pp. 151-160.
2. Groundwater, P. W., Solomons, K. R. H., Drewe, J. A., and Munawar, M. A. in "Progress in Medicinal Chemistry", Ellis, G. P. and Luscombe, D. K. Eds., Elsevier, Amsterdam, 1996, Vol 33, pp. 233-329. Fry, D. W. in "Annual Reports in Medicinal Chemistry", Bristol, J. A. Editor-in-Chief, Academic Press, San Diego, 1996, Vol 31, pp. 151-160.
3. Gishizky, M. L. in "Annual Reports in Medicinal Chemistry", Bristol, J. A. Editor-in-Chief, Academic Press, San Diego, 1995, Vol 30, pp. 247-253 and references therein.
4. Gregory, H., Hardy, P. M., Jones, D. S., Kenner, G. W., and Sheppard, R. C. Nature 1964, 204, 931.
5. Yajima, H., Mori, Y., Koyama, K., Tobe, T., Setoyama, M., Adachi, H., Kanno, T., and Saito, A. Chem. Pharm. Bull. 1976, 24, 1110. Mutt, V. and Jorpes, J. E. Eur. J. Biochem. 1968, 6, 156.
6. Yajima, H., Mori, Y., Koyama, K., Tobe, T., Setoyama, M., Adachi, H., Kanno, T., and Saito, A. Chem. Pharm. Bull. 1976, 24, 1110. Mutt, V. and Jorpes, J. E. Eur. J. Biochem. 1968, 6, 156.
7. Liu, M.-C. and Lipmann, F. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 34.
8. Nachman, R. J., Holman, G. M., Haddon, W. F., and Hayes, T. K. Pept. Res. 1989, 2, 171. Nachman, R. J., Holman, G. M., Cook, B. J., Haddon, W. R., and Ling, N. Biochem. Biophys. Res. Commun. 1986, 140, 357. Nachman, R. J., Holman, G. M., Haddon, W. F., and Ling, N. Science 1986, 234, 71.
9. Nachman, R. J., Holman, G. M., Haddon, W. F., and Hayes, T. K. Pept. Res. 1989, 2, 171. Nachman, R. J., Holman, G. M., Cook, B. J., Haddon, W. R., and Ling, N. Biochem. Biophys. Res. Commun. 1986, 140, 357. Nachman, R. J., Holman, G. M., Haddon, W. F., and Ling, N. Science 1986, 234, 71.
10. Nachman, R. J., Holman, G. M., Haddon, W. F., and Hayes, T. K. Pept. Res. 1989, 2, 171. Nachman, R. J., Holman, G. M., Cook, B. J., Haddon, W. R., and Ling, N. Biochem. Biophys. Res. Commun. 1986, 140, 357. Nachman, R. J., Holman, G. M., Haddon, W. F., and Ling, N. Science 1986, 234, 71.
11. (a) Lai, J. H., Marsilje, T. H., Choi, S., Nair, S. A., and Hangauer, D. G. J. Pept. Res. 1998, 51, 271 and references therein.
12. (b) Gonzalez-Muniz, R., Cornille, F., Bergeron, F., Ficheux, D., Pothier, J., Durieux, C., and Roques, B. P. Int. J. Pept. Protein Res. 1991, 37, 331.
13. (c) Tilley, J. W., Ramakanth, S., Wagner, R., and Mulkerins, K. J. Org. Chem. 1990, 55, 906.
14. (d) Marseigne, I. and Roques, B. P. J. Org. Chem. 1988, 53, 3621.
15. Kim, M. H., Lai, A. H., and Hangauer, D. G. Int. J. Pept. Protein Res. 1994, 44, 457.
16. (a) Smith, S. C. and Sloane, N. H. Biochim. Biophys. Acta 1967, 148, 414.
17. (b) Plaut, G. W. E. J. Med. Chem. 1965, 8, 554.
18. Morera, E. and Ortar, G. Synlett 1997, 1403. Ciattini, P. G., Morera, E., and Ortar, G. Tetrahedron Lett. 1995, 36, 4133.
19. Morera, E. and Ortar, G. Synlett 1997, 1403. Ciattini, P. G., Morera, E., and Ortar, G. Tetrahedron Lett. 1995, 36, 4133.
20. Kotsuki, H., Datta, P. K., and Suenaga, H. Synthesis 1996, 470.
21. Shieh, W.-C. and Carlson, J. A. J. Org. Chem. 1992, 57, 379.
22. Lei, H., Stoakes, M. S., Herath, K. P. B., Lee, J., and Schwabacher, A. W. J. Org. Chem. 1994, 59, 4206.
23. Dppp refers to 1,3-bis(diphenylphosphino)propane.
24. Hartman, G. D. and Halczenko, W. Synth. Commun. 1991, 21, 2103.
25. Baillargeon, V. P. and Stille, J. K. J. Am. Chem. Soc. 1986, 108, 452.
26. Sasaki, N. A., Hashimoto, C., and Potier, P. Tetrahedron Lett. 1987, 28, 6069. Brown, M. S. and Rapoport, H. J. Org. Chem. 1963, 28, 3261 and references therein.
27. Sasaki, N. A., Hashimoto, C., and Potier, P. Tetrahedron Lett. 1987, 28, 6069. Brown, M. S. and Rapoport, H. J. Org. Chem. 1963, 28, 3261 and references therein.
28. 4 and a reaction time of 1 h were found necessary for the complete reduction of the aldehyde without appreciable reduction of the ester function.