Click to fit: Versatile polyvalent display on a peptidomimetic scaffold

Organic Letters

Volumn 7, Issue 10, 2005, Pages 1951-1954

  Jang, Hangjun ^a   Fafarman, Aaron ^a   Holub, Justin M ^a   Kirshenbaum, Kent ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZIDE; GLYCINE; NUCLEIC ACID BASE; OLIGOMER; PEPTOID;

ACCURACY; ARTICLE; BINDING SITE; CONJUGATION; CYCLOADDITION; QUANTUM YIELD; SOLID; SUBSTITUTION REACTION;

COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; GLYCINE; MODELS, MOLECULAR; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; PEPTOIDS;

EID: 19544378528     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050371q     Document Type: Article

References (24)

1. Patch, J. A.; Kirshenbaum, K.; Seurynck, S. L.; Zuckermann, R. N.; Barron, A. E. In Pseudopeptides in Drug Development; Nielsen, P. E., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
2. (a) Patch, J. A.; Barron, A. E. Curr. Opin. Chem. Biol. 2002, 6, 872.
3. (b) Wu, C. W.; Kirshenbaum, K.; Sanborn, T. J.; Patch, J. A.; Huang, K.; Dill, K. A.; Zuckermann, R. N.; Barron, A. E. J. Am. Chem. Soc. 2003, 125, 13525.
4. (c) Kirshenbaum, K.; Barron, A. E.; Goldsmith, R. A.; Armand, P.; Bradley, E. K.; Truong, K. T.; Dill, K. A.; Cohen, F. E.; Zuckermann, R. N. Proc. Natl. Acad. Sci. U. S. A 1998, 95, 4303.
5. Miller, S. M.; Simon, R. J.; Ng, S.; Zuckermann, R. N.; Kerr, J. M.; Moos, W. H. Drug Dev. Res. 1995, 35, 20.
6. (a) Pei, Y. H.; Moos, W. H. Tetrahedron Lett. 1994, 35, 5825.
7. (b) Burkoth, T. S.; Fafarman, A. T.; Charych, D. H.; Connolly, M. D.; Zuckermann, R. N. J. Am. Chem. Soc. 2003, 125, 8841.
8. (c) Horn, T.; Lee, B. C.; Dill, K. A.; Zuckermann, R. N. Bioconjugate Chem. 2004, 15, 428.
9. For overview, see Kolb, H. C.; Sharpless, K. B. Drug Discov. Today 2003, 8, 1128.
10. (a) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192.
11. (b) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686.
12. (c) Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164.
13. (d) Deiters, A.; Cropp, T. A.; Mukherji, M.; Chin, J. W.; Anderson, J. C.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 11782.
14. (e) Lin, H.; Walsh, C. T. J. Am. Chem. Soc. 2004, 126, 13998
15. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
16. (b) Perez-Balderas, F.; Ortega-Munoz, M.; Morales-Sanfrutos, J.; Hernandez-Mateo, F.; Calvo-Flores, F. G.; Calvo-Asin, J. A.; Isac-Garcia, J.; Santoyo-Gonzalez, F. Org. Lett. 2003, 5, 1951.
17. (c) Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
18. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
19. (a) Nitz, M.; Mezo, A. R.; Ali, M. H.; Imperiali, B. Chem. Commun. 2002, 1912.
20. (b) Cohen, B. E.; McAnaney, T. B.; Park, E. S.; Jan, Y. N.; Boxer, S. G.; Jan, L. Y. Science 2002, 296, 1700.
21. A full report of our synthesis of this 6-azido-acetyl analogue and its application is forthcoming.
22. Wu, P.; Feldman, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2004, 43, 3928.
23. Lewis, W. G.; Magallon, F. G.; Fokin, V. V.; Finn, M. G. J. Am. Chem. Soc. 2004, 126, 9152.
24. Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754.