Synthesis of alanine and proline amino acids with amino or guanidinium substitution on the side chain

Tetrahedron

Volumn 56, Issue 16, 2000, Pages 2513-2522

  Zhang, Zhenyu ^a   Aerschot, Arthur Van ^a   Hendrix, Chris ^a   Busson, Roger ^a   David, Frank ^b   Sandra, Pat ^b   Herdewijn, Piet ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^b Research Institute for Chromatography   (Belgium)

Author keywords

Guanidinium substitution; HIV replication; Tat TAR interaction

Indexed keywords

ALANINE; GUANIDINE; PROLINE;

AMINO ACID SUBSTITUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; LIGAND BINDING; MASS SPECTROMETRY; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0034647018     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00123-X     Document Type: Article

References (25)

1. Declercq E. Collect. Czech. Chem. Commun. 63:1998;449-479.
2. Declercq E. Trends Drug Res. II. 1998;91-104.
3. Declercq E. Int. J. Antimicrob. Agents. 9:1997;21-36.
4. Kingsman S.M., Kingsman A.J. Eur. J. Biochem. 240:1996;491-507.
5. Frankel A.D. Curr. Opin. Genet. Dev. 2:1992;293-298.
6. Calnan B.J., Tidor B., Biancalana S., Hudson D., Frankel A.D. Science. 252:1991;1167-1171.
7. Puglisi J.D., Tan R., Canlan B.J., Frankel A.D., Williamson J.R. Science. 257:1992;76-80.
8. Aboul-ela F., Karn J., Varani G. J. Mol. Biol. 253:1995;313-332.
9. Terrett N.K., Gardner M., Gordon D.W., Kobylecki R.J., Steele J. Tetrahedron. 51:1995;8135-8173.
10. Medynski D. Biotechnology. 12:1994;709-710.
11. Houghten R.A., Pinilla C., Blondelle S.E., Appel J.R., Dooley C.T., Cuervo J.H. Nature. 354:1991;84-86.
12. Youngquist R.S., Fuentes G.R., Lacey M.P., Keough T. J. Am. Chem. Soc. 117:1995;3900-3906.
13. Löbberding, A., Mielke, B., Schwemler, C., Schwenner, E., Stropp, U., Springer, W., Kretschmer, A., Pötter, T. In Nukleinsäuren-bindende Oligomere mit N-Verzweigung für Therapie und Diagnostik (EP 0 646 595 A1).
14. Arnold L.D., Kalantar T.H., Vederas J.C. J. Am. Chem. Soc. 107:1985;7105-7109.
15. Waki M., Kitajima Y., Izumiya N. Synthesis. 1981;266-268.
16. Yong Y.F., Kowalski J.A., Lipton M.A. J. Org. Chem. 62:1997;1540-1542.
17. Shibanuma T., Shiono M., Mukaiyama T. Chem. Lett. 1977;575-576.
18. Kim K.S., Qian L. Tetrahedron Lett. 34:1993;7677-7680.
19. Feichtinger K., Zapf C., Sings H.L., Goodman M. J. Org. Chem. 63:1998;3804-3805.
20. Uno T., Beausoleil E., Goldsmith R.A., Levin B.H., Zuckermann R.N. Tetrahedron Lett. 40:1999;1475-1478.
21. Bernatowicz M.S., Wu Y., Matsueda G.R. J. Org. Chem. 57:1992;2497-2502.
22. Rzeszotarska B., Masiukiewicz E. Org. Prep. Proced. Int. 20:1988;427-464.
23. Rink H., Sieber P., Raschdorf F. Tetrahedron Lett. 25:1984;621-624.
24. Atherton E., Sheppard R.C., Wade J.D. J. Chem. Soc. Chem. Commun. 1983;1060-1062.
25. Ramage R., Green J., Blake A.J. Tetrahedron. 47:1991;6353-6370.