Enzymatic syntheses of 6-(4H-selenolo[3,2-b]pyrrolyl)-L-alanine, 4-(6H- selenolo[2,3-b]pyrrolyl)-L-alanine, and 6-(4H-furo[3,2-b]pyrrolyl)-L-alanine

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 5, 1999, Pages 637-640

  Welch, Michael ^a   Phillips, Robert S ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (6H SELENOLO[2,3 B]PYRROLYL)ALANINE; 6 (4H FURO[3,2 B]PYRROLYL)ALANINE; 6 (4H SELENOLO[3,2 B]PYRROLYL)ALANINE; FURO[3,2 B]PYRROLE; SELENIUM DERIVATIVE; SELENOLO[2,3 B]PYRROLE; SELENOLO[3,2 B]PYRROLE; SERINE; TRYPTOPHAN DERIVATIVE; TRYPTOPHAN SYNTHASE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; FILTRATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; X RAY CRYSTALLOGRAPHY;

ALANINE; CELL DIVISION; ESCHERICHIA COLI; FURANS; ORGANOSELENIUM COMPOUNDS; SALMONELLA TYPHIMURIUM; TRYPTOPHAN; TRYPTOPHAN SYNTHASE;

SALMONELLA TYPHIMURIUM; TYPHIMURIUM;

EID: 0033535444     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00067-0     Document Type: Article

References (12)

1. Sloan, M.; Phillips, R. S. Bioorg. Med. Chem. Lett. 1992, 2, 1053.
2. Lee, M.; Phillips, R. S. Bioorg. Med. Chem. Lett. 1992, 2, 1563.
3. Phillips, R. S.; Cohen, L. A.; Annby, U.; Wensbo, D.; Gronowitz, S. Bioorg. Med. Chem. Lett. 1995, 5, 1133.
4. For a review, see Besse, D.; Busida, N.; Karnbrock, W.; Minks, C.; Musiol, H. J.; Pegoraro, S.; Siedler, F.; Weyher, E.; Moroder, L. Biolog. Chem. 1997, 378, 211.
5. To call attention to the similiarity of compounds 1-3 to L-tryptophan, we suggest the following trivial names: 1 - 4,5-selena-L-tryptophan; 2 - 6,7-selena-L-tryptophan; 3 - 4,5-oxa-L-tryptophan. The numerical locants which begin all three of the trivial names describe the numbers of the two carbon atoms in L-tryptophan which are replaced by either selenium, for compounds 1 and 2, or oxygen, for compound 3. These trivial names were generated with reference to the general guidelines for replacement nomenclature for heterocyclic compounds.
6. Original syntheses of the selenolo-, thieno-, and furopyrroles: Soth, S.; Farnier, M.; and Paulmier, C. Can. J. Chem. 1978, 56, 1429.
7. Improved syntheses of the selenolo-, thieno-, and furopyrroles: Welch, M.; Phillips, R. S. (in preparation).
8. 2 at 0 °C.
9. 2O, 62.5 MHz, ppm) 35.8, 57.5, 93.2, 100.2, 122.2, 127.1, 149.7, 156.2, 182.5. LD-MS(m/z, no matrix): 271(M + 2K - 1H); 233(M + 1K); unassigned peaks exist @ 255 and 213. Each is less than 40% the intensity of the two assigned peaks.
10. nd ASMS Conference on Mass Spectrometry and Allied Topics, May 29-June 3, 1994, Chicago, Illinois, 1994, 640.
11. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. In Spectrometric Identification of Organic Compounds; John Wiley & Sons: New York, 1991; Vol. 5, pp 11-12.
12. 9