Triazolopeptides: chirospecific synthesis and cis/trans prolyl ratios of structural isomers

Tetrahedron

Volumn 62, Issue 38, 2006, Pages 8919-8927

  Paul, Andreas ^a   Bittermann, Holger ^a   Gmeiner, Peter ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Azide alkyne cycloaddition; cis trans Prolyl isomerization; Click chemistry; Triazolopeptide

Indexed keywords

ALKYNE; AZIDE; PEPTIDE DERIVATIVE; PROLINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CIS TRANS ISOMERISM; CYCLOADDITION; HYDROGEN BOND; ISOMERIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 33746803733     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.007     Document Type: Article

References (37)

1. Jabs A., Weiss M.S., and Hilgenfeld R. J. Mol. Biol. 286 (1999) 291-304
2. Dugave C., and Demange L. Chem. Rev. 103 (2003) 2475-2532 and references cited therein
3. Lummis S.C.R., Beene D.L., Lee L.W., Lester H.A., Broadhurst R.W., and Dougherty D.A. Nature 438 (2005) 248-252
4. Wittelsberger A., Keller M., Scarpellino L., Partiny L., Acha-Orbea H., and Mutter M. Angew. Chem., Int. Ed. 39 (2000) 1111-1115
5. Angew. Chem. 112 (2000) 1153-1156
6. Kern D., Schutkowski M., and Drakenberg T. J. Am. Chem. Soc. 119 (1997) 8403-8408
7. Halab L., and Lubell W.D. J. Org. Chem. 64 (1999) 3312-3321
8. An S.S.A., Lester C.C., Peng J.-L., Li Y.-J., Rothwarf D.M., Welker E., Thannhauser T.W., Zhang L.S., Tam J.P., and Scheraga H.A. J. Am. Chem. Soc. 121 (1999) 11558-11566
9. Bretscher L.E., Jenkins C.L., Taylor K.M., DeRider M.L., and Raines R.T. J. Am. Chem. Soc. 123 (2001) 777-778
10. Renner C., Alefelder S., Bae J.H., Budisa N., Huber R., and Moroder L. Angew. Chem., Int. Ed. 40 (2001) 923-925
11. Gramberg D., Weber C., Beeli R., Inglis J., Bruns C., and Robinson J.A. Helv. Chim. Acta 78 (1995) 1588-1606
12. Curran T.P., and McEnaney P.M. Tetrahedron Lett. 36 (1995) 191-194
13. Kim K., Dumas J.-P., and Germanas J.P. J. Org. Chem. 61 (1996) 3138-3144
14. Hoffmann T., Lanig H., Waibel R., and Gmeiner P. Angew. Chem. 113 (2001) 3465-3468
15. Angew. Chem., Int. Ed. 40 (2001) 3361-3364
16. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596-2599
17. Angew. Chem. 114 (2002) 2708-2711
18. Tornøe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3064
19. Kolb H.C., and Sharpless K.B. Drug Discov. Today 8 (2003) 1128-1137
20. Mocharla V.P., Colasson B., Lee L.V., Röper S., Sharpless K.B., Wong C.H., and Kolb H.C. Angew. Chem. 44 (2005) 116-120
21. Bettinetti L., Löber S., Hübner H., and Gmeiner P. J. Comb. Chem. 7 (2005) 309-316
22. Rodriguez Loaiza P., Löber S., Hübner H., and Gmeiner P. J. Comb. Chem. 8 (2006) 252-261
23. Van Maarseveen J.H., Horne W.S., and Ghadiri M.R. Org. Lett. 7 (2005) 4503-4506 and references cited therein
24. Bock V.D., Perciaccante R., Jansen T.P., Hiemstra H., and Van Maarseveen J.H. Org. Lett. 8 (2006) 919-922
25. Angelo N.G., and Arora P.S. J. Am. Chem. Soc. 127 (2005) 17134-17135
26. Zhang Z., and Fan E. Tetrahedron Lett. 47 (2006) 665-669
27. Trybulski E.J., Kramss R.H., Mangano R.M., and Rusinko A. J. Med. Chem. 33 (1990) 3190-3198
28. Cossy J., Cases M., and Pardo D.G. Bull. Soc. Chim. Fr. 134 (1997) 141-144
29. Markidis T., and Kokotos G. J. Org. Chem. 66 (2001) 1919-1923
30. Kimball, S. D.; Das, J.; Lau W. F.; Hall, S. E.; Han W. -C. U.S. Patent 5,583,146, 1996.
31. Norris P., Horton D., and Levine B.R. Heterocycles 43 (1996) 2643-2655
32. Guanti G., and Riva R. Tetrahedron: Asymmetry 12 (2001) 1185-1200
33. Lundquist IV J.T., and Pelletier J.C. Org. Lett. 3 (2001) 781-783
34. Zabrocki J., Smith G.D., Dunbar Jr. J.B., Iijima H., and Marshall G.R. J. Am. Chem. Soc. 110 (1988) 5875-5880
35. Ishimoto B., Tonan K., and Ikawa S.-i. Spectrochim. Acta, Part A 56 (1999) 201-209
36. Horne W.S., Yadav M.K., Stout D., and Ghadiri M.R. J. Am. Chem. Soc. 126 (2004) 15366-15367
37. Zhang L., Chen X., Xue P., Sun H.H.Y., Williams I.D., Sharpless K.B., Fokin V.V., and Jia G. J. Am. Chem. Soc. 127 (2005) 15998-15999