A facile and one-pot synthesis of Nα-Fmoc/Bsmoc/Boc/Z-protected ureidopeptides and peptidyl ureas employing diphenylphosphoryl azide [DPPA]

Tetrahedron Letters

Volumn 49, Issue 8, 2008, Pages 1408-1412

  Sureshbabu, Vommina V ^a   Chennakrishnareddy, G ^a   Narendra, N ^a  

^a Dr B R Ambedkar Veedhi   (India)

Author keywords

Curtius rearrangement; Diphenylphosphoryl azide; One pot synthesis; Peptidyl ureas; Ureidopeptides

Indexed keywords

1,1 DIOXOBENZO[B]THIOPHEN 2 YLMETHYLOXYCARBONYL; AMINO ACID; AZIDE; BUTYL OXY CARBONYL; CARBAMIC ACID METHYL ESTER; CARBONYL DERIVATIVE; DIPHENYLPHOSPHORYL AZIDE; FLUORENYL METHOXY CARBONYL; PEPTIDE DERIVATIVE; PEPTIDYL UREA DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE; UREIDOPEPTIDE DERIVATIVE;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; SPECTROSCOPY; SYNTHESIS;

EID: 38349112611     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.060     Document Type: Article

References (37)

1. Nowick J.S., Smith E.M., and Pairish M. Chem. Soc. Rev. 25 (1996) 401-415
2. Lam P.Y., Jadhav P.K., Eyermann C.J., Hodge C.N., Ru Y., Bacheler L.T., Meek J.L., Otto M.J., Rayner M.M., Wong Y.N., Chang C.-H., Weber P.C., Jackson D.A., Sharpe T.R., and Erickson-Viitanen S. Science 263 (1994) 380-384
3. Burgess K., Shin H., and Linthicum D.S. Angew. Chem., Int. Ed. Engl. 34 (1995) 907-909
4. Wang X., Huq I., and Rana T.M. J. Am. Chem. Soc. 119 (1997) 6444-6445
5. Cho C.Y., Moran E.J., Cherry S.R., Stephans J.C., Fodor S.P., Adams C.L., Sundaram A., Jacobs J.W., and Schultz P.G. Science 261 (1993) 1303-1305
6. Navia M.A., Fitzgerald P.M.D., McKeever B.M., Leu C.-T., Heimbach J.C., Herber W.K., Sigal I.S., Darke P.L., and Springer J.P. Nature 337 (1989) 615-620
7. Bakshi P., and Wolfe M.S. J. Med. Chem. 47 (2004) 6485-6489
8. Kick E.K., and Ellman J.A. J. Med. Chem. 38 (1995) 1427-1430
9. Broadbridge R.J., Sharma R.P., and Akhtar M. Chem. Commun. (1998) 1449-1450
10. Dales N.A., Bohacek R.S., Satyshur K.A., and Rich D.H. Org. Lett. 3 (2001) 2313-2316
11. Kawasaki K., Maeda M., Watanabe J., and Kaneto H. Chem. Pharm. Bull. 36 (1988) 1766-1771
12. Vegner R.E., and Chipens G.I. J. Gen. Chem. USSR (Engl. Transl.) 45 (1975) 431-434
13. Rodriguez M., Dubreuil P., Bali J.P., and Martinez J. J. Med. Chem. 30 (1987) 758-763
14. Guerlavais V., Boegglin D., Mousseaux D., Oiry C., Heitz A., Deghengi R., Locatelli V., Torsello A., Ghe C., Catapano F., Muccioli G., Galleyrand J.-C., Fehrentz J.-A., and Martinez J. J. Med. Chem. 46 (2003) 1191-1203
15. Teng H., He Y., Wu L., Su J., Feng X., Qiu G., Liang S., and Hu X. Synlett (2006) 877-880
16. Semetey V., Didierjean C., Briand J.-P., Aubry A., and Guichard G. Angew. Chem., Int. Ed. 41 (2002) 1895-1898
17. Fischer L., Semetey V., Lozano J.-M., Schaffner A.P., Briand J.-P., Didierjean C., and Guichard G. Eur. J. Org. Chem. 15 (2007) 2511-2525
18. Patil B.S., Vasanthakumar G.R., and Sureshbabu V.V. J. Org. Chem. 68 (2003) 7274-7280
19. Sureshbabu V.V., Patil B.S., and Venkatramanarao R. J. Org. Chem. 71 (2006) 7697-7705
20. Patil B.S., and Sureshbabu V.V. Lett. Pept. Sci. 10 (2003) 93-97
21. Sureshbabu V.V., Ananda K., and Vasanthakumar G.R. J. Chem. Soc., Perkin Trans. 1 (2000) 4328-4331
22. Myers A.C., Kowalski J.A., and Lipton M.A. Bioorg. Med. Chem. Lett. 14 (2004) 5219-5222
23. Englund E.A., Gopi H.N., and Appella D.H. Org. Lett. 6 (2004) 213-215
24. Smith P.A.S. Org. React. 3 (1946) 337-449
25. Jacobi P.A., and Zheng W. Tetrahedron Lett. 34 (1993) 2581-2584
26. Shao H., Colucci M., Tong S., Zhang H., and Castelhano A.L. Tetrahedron Lett. 39 (1998) 7235-7238
27. Wu Y., Esser L., and De Brabander J.K. Angew. Chem., Int. Ed. 39 (2000) 4308-4310
28. Kedrowski B.L. J. Org. Chem. 68 (2003) 5403-5406
29. Yamada S., Ikota N., Shioiri T., and Tachibana S. J. Am. Chem. Soc. 97 (1975) 7174-7175
30. Ninomiya K., Shioiri T., and Yamada S. Tetrahedron 30 (1974) 2151-2157
31. Lal B., Pramanik B.N., Manhas M.S., and Bose A.K. Tetrahedron Lett. 18 (1977) 1977-1980
32. Richter L.S., and Andersen S. Tetrahedron Lett. 39 (1998) 8747-8750
33. Daisuke S.D., Sasayama S., Takahashi H., and Ikegami S. Tetrahedron Lett. 47 (2006) 7219-7223
34. In: Goodman M., Felix A., Moroder L., and Toniolo C. (Eds). Houben-Weyl: Synthesis of Peptides & Peptidomimetics Vol. E22c (2003), Georg Thieme, Stuttgart, New York and references cited therein
35. Scriven E.F.V., and Turnbull K. Chem. Rev. 88 (1988) 297-368
36. 3 doublets when optically pure phenylethylamines were coupled) during the reaction. Instead, the reaction resulted in optically pure product.
37. Karle I.L., Pramanik A., Banerjee A., Bhattacharjya S., and Balaram P. J. Am. Chem. Soc. 119 (1997) 9087-9095