Design, synthesis, and validation of rigid linkers for bioactive peptides

Tetrahedron Letters

Volumn 46, Issue 44, 2005, Pages 7589-7592

  Monguchi, Yasunari ^a   Vagner, Josef ^a   Handl, Heather L ^b   Jana, Umasish ^a   Begay, Lucinda J ^a   Hruby, Victor J ^a,b   Gillies, Robert J ^b   Mash, Eugene A ^a  

^a University of Arizona   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 NAPHTHOIC ACID DERIVATIVE; ALPHA INTERMEDIN; ALPHA INTERMEDIN DERIVATIVE; PEPTIDE DERIVATIVE;

ARTICLE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; LIGAND BINDING; PEPTIDE SYNTHESIS; SOLID PHASE SYNTHESIS; VALIDATION PROCESS;

EID: 26244439921     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.151     Document Type: Article

References (21)

1. H.L. Handl, J. Vagner, H. Han, E. Mash, V.J. Hruby, and R. Gillies J. Expert Opin. Ther. Targets 8 2004 565 586
2. M. Mammen, S.-K. Choi, and G.M. Whitesides Angew. Chem., Int. Ed. 37 1998 2754 2794
3. L.L. Kiessling, and J.E. Gestwicki Curr. Opin. Chem. Biol. 4 2000 696 703
4. J. Vagner, H.L. Handl, R.J. Gillies, and V.J. Hruby Bioorg. Med. Chem. Lett. 14 2004 211 215
5. N. Raju, R.S. Ranganathan, M.F. Tweedle, and R.E. Swenson Tetrahedron Lett. 46 2005 1463 1465
6. W. Maison, J.V. Frangioni, and N. Pannier Org. Lett. 6 2004 4567 4569
7. On balance the series of linkers should be hydrophilic, but short hydrophobic segments may be tolerated, if not beneficial.
8. Purchased from Torviq, Niles MI.
9. S. Manku, F. Wang, and D.G. Hall J. Comb. Chem. 5 2003 379 391
10. Purchased from CombiBlocks, San Diego, CA.
11. Purchased from Aldrich Chemical Company.
12. Distances between the benzylic carbon atoms: 1, 5.8 Å; 2, 10.0 Å; 3, 14.3 Å; and 4, 12.2 Å; determined using AM1 in Spartan '02 v1.0.4e.
13. P.S. van Heerden, B.C.B. Bezuidenhoudt, and D. Ferreira J. Chem. Soc., Perkin Trans. 1 1997 1141 1146
14. Purchased from Acros Organics.
15. T.K. Sawyer, P.J. Sanfilippo, V.J. Hruby, M.H. Engel, C.B. Heward, J.B. Burnett, and M.E. Hadley Proc. Natl. Acad. Sci. U.S.A. 77 1980 5754 5755
16. M.E. Hadley, B. Anderson, C.B. Heward, T.K. Sawyer, and V.J. Hruby Science 213 1981 1025 1027
17. R.B. Merrifield J. Am. Chem. Soc. 85 1963 2149 2154
18. V.J. Hruby, and J.-P. Meyer S.M. Hecht Bioorganic Chemistry: Peptides and Proteins 1988 Oxford Univ. Press New York 27 64
19. Details will appear in a full paper to follow.
20. H.L. Handl, J. Vagner, H.I. Yamamura, V.J. Hruby, and R.J. Gillies Anal. Biochem. 330 2004 242 250
21. The hMC4R vector was originally received from Dr. Ira Gantz; see: I. Gantz, H. Miwa, Y. Konda, Y. Shimoto, T. Tashiro, S.J. Watson, J. Delvalle, and T. Yamada J. Biol. Chem. 268 1993 15174 15179