Improved preparation of racemic 2-amino-3-(heteroaryl)propanoic acids and related compounds containing a furan or thiophene nucleus

Chemical and Pharmaceutical Bulletin

Volumn 52, Issue 9, 2004, Pages 1137-1139

  Kitagawa, Tokujiro ^a   Khandmaa, Dashrenchin ^a,b   Fukumoto, Ayumi ^a   Asada, Makoto ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b MONGOLIAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Mongolia)

Author keywords

3 (furan 2 yl)alanine; Hydroxyimino acid; N formyl amino acid; Reduction; Unnatural amino acid

Indexed keywords

ACETIC ANHYDRIDE; ALANINE DERIVATIVE; BROMINE; FORMIC ACID; FURAN DERIVATIVE; IRON; PROPIONIC ACID DERIVATIVE; THIOPHENE DERIVATIVE; ZINC; AMINO ACID; FORMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL COMPOSITION; HYDROGENOLYSIS; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; OXIDATION REDUCTION REACTION;

AMINO ACIDS; CATALYSIS; FORMIC ACIDS; FURANS; IRON; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PROPIONIC ACIDS; THIOPHENES; ZINC;

EID: 16644398651     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.52.1137     Document Type: Article

References (36)

1. ChemFiles 2001 Vol.1, No. 5, Unnatural Amino Acids, Sigma-Aldrich. [http://www.sigmaaldrich.com/img/assets/6040/chemFiles_v1n5_ unnaturalaa_small.pdf], PSJ Web, 29 March, 2004.
2. ChemFiles 2002 Vol.2, No. 4, Unnatural Amino Acids II, Sigma-Aldrich. [http://www.sigmaaldrich.com/img/assets/6040/Amino_ Acids_IINP.pdf], PSJ Web, 29 March, 2004.
3. Kretzschmar G., Hoppe H. U., Wicke H., Schlingmann M., Keller R., Sachse B., Ger. Offen. DE 38 20 302 A1 (21 Dec., 1989) [Chem. Abstr., 113, 23677s (1990)].
4. Kretzschmar G., Wicke H., Sachse B., Ger. Offen, DE 38 29 451 (1 Mar., 1990) [Chem. Abstr., 113, 115862b (1990)].
5. Ma J. S., Chimica Oggi, 6, 65-68 (2003), [http://www.peptechcorp.-com/ index.asp], PWJ Web. 29 March, 2004.
6. Kitagawa T., Nakamura M., Masai K., Chem. Pharm. Bull., 51, 994-998 (2003).
7. Sasaki T., Chem. Ber., 54, 2056-2059 (1921).
8. Deulofeu V., Z. Physiol. Chem., 204, 214-218 (1932).
9. Badshah A., Khan N. H., Kidwai A. R., J. Org. Chem., 37, 2916-2918 (1972).
10. Gränacher C., Helv. Chim. Acta, 5, 610-624 (1922).
11. Plucker J., III, Amstutz E. D., J. Am. Chem. Soc., 62, 1512-1513 (1940).
12. Brown F. C., Bradsher C. K., Bond S. M., Grantham R. J., Ind. Eng. Chem., 46, 1508-1512 (1954).
13. Watanabe H., Kuwata S., Nakajima S., Koshida K., Hayashi M., Bull. Chem. Soc. Japan, 38, 1461-1464 (1965).
14. Herz W., Dittmer K., Cristol S. J., J. Biol. Chem., 171, 383-386 (1947).
15. Bladon C. M., J. Chem. Soc., Perkin Trans. 1, 1990, 1151-1158 (1990).
16. Chenault H. K., Dahmer J., Whitesides G. M., J. Am. Chem. Soc., 111, 6354-6364 (1989).
17. Kitagawa T., Akiyama N., Chem. Pharm. Bull., 45, 1865-1866 (1997).
18. Divald S., Chun M. C., Joullie M. M., J. Org. Chem., 41, 2835-2846 (1976).
19. Craig L. C., J. Am. Chem. Soc., 55, 2854-2857 (1933).
20. Galat A., J. Am. Chem. Soc., 69, 965 (1947).
21. Shaw K. N. F., Nolan C., J. Org. Chem., 22, 1668-1670 (1957).
22. Galun A. B., J. Chem. Eng. Data, 21, 241 (1976).
23. Crowe B. F., Nord F. F., J. Org. Chem., 15, 688-693 (1950).
24. Ferger M. F., du Vigneaud V., J. Biol. Chem., 174, 241-246 (1948).
25. Julian P. L., Sturgis B. M., J. Am. Chem. Soc., 57, 1126-1128 (1935).
26. Tsuchiya C., Nippon Kagaku Zasshi, 81, 979-981 (1960)
27. [Chem. Abstr., 56, 10265c (1962)].
28. Modarram H. H., Abdel-Fattah A. M., El-Merzabani M. M., Mansour S. A., Egypt. J. Chem., 26, 301-311 (1983)
29. [Chem. Abstr., 101, 230399v (1984)].
30. Kitagawa T., Kawaguchi M., Ikiuchi M., Chem. Pharm. Bull., 39, 187-189 (1991).
31. Go M. L., Leung S. L., Acta Pharm. Suec., 21, 77-80 (1984).
32. Lewis D. E., Dunn F. W., J. Arch. Biochem. Biophys., 107, 363-366 (1964)
33. [Chem. Abstr., 61, 11050g (1964)].
34. du Vigneaud V., McKennis H., Jr., Simmonds S., Dittmer K., Brown G. B., J. Biol. Chem., 159, 385-394 (1945).
35. Campaigne E., Bourgeois R. C., Garst R., McCarthy W. C., Patrick R. L., Day H. G., J. Am. Chem. Soc., 70, 2611 (1848).
36. Dittmer K., Martin R. D., Herz W., Cristol S. J., J. Am. Chem. Soc., 71, 1201-1204 (1949).