Synthesis of L-aminohomohistidine (L-Ahh)

Tetrahedron Letters

Volumn 45, Issue 13, 2004, Pages 2779-2781

  Friedel, Manuel ^a   Lindel, Thomas ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Amino acids; Aminoimidazoles; Arginine mimetic; Bioisosteres; Medicinal chemistry

Indexed keywords

AMINO ACID DERIVATIVE; GUANIDINE DERIVATIVE; IMIDAZOLE DERIVATIVE; LYSINE DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; GEL CHROMATOGRAPHY;

EID: 1542358708     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.027     Document Type: Article

References (21)

1. Peterlin-Mašič L., Kikelj D. Tetrahedron. 57:2001;7073-7105.
2. Leung D., Abbenante G., Fairlie D.P. J. Med. Chem. 43:2000;305-341.
3. Haubner R., Finsinger D., Kessler H. Angew. Chem., Int. Ed. 36:1997;1374-1389.
4. Alderton W.K., Cooper C.E., Knowles R.G. Biochem. J. 357:2001;593-615. and references cited therein.
5. For a leading reference, see: Lam P.Y.S., Clark C.G., Li R., Pinto D.J.P., Orwat M.J., Galemmo R.A., Fevig J.M., Teleha C.A., Alexander R.S., Smallwood A.M., Rossi K.A., Wright M.R., Bai S.A., He K., Luettgen J.M., Wong P.C., Knabb R.M., Wexler R.R. J. Med. Chem. 46:2003;4405-4418.
6. Soll R.M., Lu T., Tomczuk B., Illig C.R., Fedde C., Eisennagel S., Bone R., Murphy L., Spurlino J., Salemme F.R. Bioorg. Med. Chem. Lett. 10:2000;1-4.
7. Reviews on the pyrrole-imidazole alkaloids: Al Mourabit A., Potier P. Eur. J. Org. Chem. 2001;237-243.
8. Hoffmann H., Lindel T. Synthesis. 2003;1753-1783.
9. Storey B.T., Sullivan W.W., Moyer C.L. J. Org. Chem. 29:1964;3118-3120.
10. Patent claims on derivatives: Conolly, C.; Doherty, A. M.; Hamilton, H. W.; Patt, W. C.; Sircar, I. (Warner-Lambert Co., USA). Eur. Pat. Appl. EP 399556, 1990.
11. Haik, G. M., Jr. (Redox Inc., USA.). PCT Int. Appl. WO 9717081, 1997.
12. Haik, G. M., Jr. (Redox Inc., USA). PCT Int. Appl. WO 9851260, 1998.
13. (5S)-Hydroxy-L-lysine ( 4 ) is also commercially available.
14. Lindel T., Hochgürtel M., Assmann M., Köck M. J. Nat. Prod. 63:2000;1566-1569.
15. Schwyzer R., Rittel W. Helv. Chim. Acta. 44:1961;161.
16. Broddefalk J., Bäcklund J., Almqvist F., Johansson M., Holmdahl R., Kihlberg J. J. Am. Chem. Soc. 120:1998;7676-7683.
17. Lancini G.C., Lazzari E. J. Heterocycl. Chem. 3:1966;152-154.
18. Bernatowicz M.S., Wu Y., Matsueda G.R. Tetrahedron Lett. 34:1993;3389-3392.
19. Bernatowicz M.S., Wu Y., Matsueda G.R. J. Org. Chem. 57:1992;2497-2502.
20. +: calcd 185.1039; found 185.1026.
21. Lide D.R. Handbook of Chemistry and Physics. 76th ed. 1995;CRC, Boca Raton. p 7-1.