H-bonding directed one-step synthesis of novel macrocyclic peptides from ε-aminoquinolinecarboxylic acid

Tetrahedron Letters

Volumn 50, Issue 20, 2009, Pages 2367-2369

  Li, Fei ^a   Gan, Quan ^b,c   Xue, Lin ^b,c   Wang, Zhong ming ^a   Jiang, Hua ^b  

^a BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

^b INSTITUTE OF CHEMISTRY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Aggregation; Macrocycles; Oligopeptides; One step synthesis

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; EPSILON AMINOQUINOLINECARBOXYLIC ACID; MACROCYCLIC COMPOUND; PEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; HYDROGEN BOND; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 63349107282     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.207     Document Type: Article

References (22)

1. For reviews, see:. Zhang W., and Moore J.S. Angew. Chem., Int. Ed. 45 (2006) 4416-4439
2. Li Z.-T., Hou J.-L., Li C., and Yi H.-P. Chem. Asian. J. 1 (2006) 766-788
3. Li Z.-T., Hou J.-L., and Li C. Acc. Chem. Res. 41 (2008) 1343-1353
4. Gong B. Acc. Chem. Res. 41 (2008) 1376-1386
5. For examples, see:. Pan G.-B., Cheng X.-H., Höger S., and Freyland W. J. Am. Chem. Soc. 128 (2006) 4218-4219
6. Shu L., and Mayor M. Chem. Commun. (2006) 4134-4136
7. Naddo T., Che Y., Zhang W., Balakrishnan K., Yang X., Yen M., Zhao J., Moore J.S., and Zang L. J. Am. Chem. Soc. 129 (2007) 6978-6979
8. Sanford A.R., Yuan L., Feng W., Yamato K., Flowers R.A., and Gong B. Chem. Commun. (2005) 4720-4722
9. Zhu Y.-Y., Li C., Li G.-Y., Jiang X.-K., and Li Z.-T. J. Org. Chem. 73 (2008) 1745-1751
10. Helsel A.J., Brown A.L., Yamato K., Feng W., Yuan L., Clements A.J., Harding S.V., Szabo G., Shao Z., and Gong B. J. Am. Chem. Soc. 130 (2008) 15784-15785
11. Masu H., Okamoto T., Kato T., Katagiri K., Tominaga M., Goda H., Takayanagi H., and Azumaya I. Tetrahedron Lett. 47 (2006) 803-807
12. Kang S.W., Gothard C.M., Maitra S., Atiatul W., and Nowick J.S. J. Am. Chem. Soc. 129 (2007) 1486-1487
13. Campbell P., Plante J., Carruthesrs C., Hardie M.J., Prior T.J., and Wilson A.J. Chem. Commun. (2007) 2240-2242
14. Bong D.T., Clark T.D., Granja J.R., and Ghadiri M.R. Angew. Chem., Int. Ed. 40 (2001) 988-1011
15. Jiang H., Léger J.M., Guionneau P., and Huc I. Org. Lett. 6 (2004) 2985-2988
16. Shirude P.S., Gillies E.R., Ladame S., Godde F., Shin-ya K., Huc I., and Balasubramanian S. J. Am. Chem. Soc. 129 (2007) 11890-11891
17. Gan Q., Bao C., Kauffmann B., Gréard A., Xiang J., Liu S., Huc I., and Jiang H. Angew. Chem., Int. Ed. 47 (2008) 1715-1718
18. Heindel N.D., Bechara I.S., Lemke T.F., and Fish V.B. J. Org. Chem. 32 (1967) 4155-4157
19. Regarding dichlorotriphenylphopshorane as an amide coupling reagent, its possible mechanism see:. Azumaya I., Okamoto T., Imabeppu F., and Takayanagi H. Tetrahedron 59 (2003) 2325-2331
20. + 1559.0, found 1559.8.
21. -1, CCDC-715184.
22. Janiak C. J. Chem. Soc., Dalton Trans. (2000) 3885-3896