Cross-metathesis and ring-closing metathesis reactions of amino acid-based substrates

Tetrahedron

Volumn 64, Issue 18, 2008, Pages 3980-3997

  Vernall, Andrea J ^a   Ballet, Steven ^b,c   Abell, Andrew D ^a,c  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

^b VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

^c UNIVERSITY OF ADELAIDE   (Australia)

Author keywords

Amino acid dimerization; Cross metathesis (CM); Cyclic amino acids; Ring closing metathesis (RCM)

Indexed keywords

ALKENE DERIVATIVE; AMINO ACID; ARGININE; CYSTINE; MACROCYCLIC COMPOUND; PHENYLALANINE; SERINE; TYROSINE;

AMINO ACID SYNTHESIS; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS METATHESIS; CYCLIZATION; DIMERIZATION; OLEFINATION; PRIORITY JOURNAL; RING CLOSING METATHESIS;

EID: 40849140628     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.043     Document Type: Article

References (56)

1. Heldin C. Cell 80 (1995) 213-223
2. Balasubramanian D., and Kanwar R. Mol. Cell. Biochem. 234/235 (2002) 27-38
3. Miller A.G., Meade S.J., and Gerrard J.A. Bioorg. Med. Chem. 11 (2003) 843-852
4. Cobb B.A., and Kasper D.L. Eur. J. Immunol. 35 (2005) 352-356
5. Paulson J.C. Trends Biochem. Sci. 14 (1989) 272-276
6. Adessi C., and Soto C. Curr. Med. Chem. 9 (2002) 963-978
7. Carrithers M.D., and Lerner M.R. Chem. Biol. 3 (1996) 537-542
8. Lazarus L.H., Guglietta A., Wilson W.E., Irons B.J., and de Casteglione R. J. Biol. Chem. 264 (1989) 354-362
9. Hultsch C., Pawelke B., Bergmann R., and Wuest F. Bioorg. Med. Chem. 14 (2006) 5913-5920
10. Stewart J.M. Peptides 25 (2004) 527-532
11. Li T., Fujita Y., Shiotani K., Miyazaki A., Tsuda Y., Ambo A., Sasaki Y., Jinsmaa Y., Marczak E., Bryant S.D., Salvadori S., Lazarus L.H., and Okada Y. J. Med. Chem. 48 (2005) 8035-8044
12. Krajewski K., Long Y., Marchand C., Pommier Y., and Roller P.P. Bioorg. Med. Chem. Lett. 13 (2003) 3203-3205
13. Krajewski K., Marchand C., Long Y., Pommier Y., and Roller P.P. Bioorg. Med. Chem. Lett. 14 (2004) 5595-5598
14. Okada Y., Tsuda Y., Fujita Y., Yokoi T., Sasaki Y., Ambo A., Konishi R., Nagata M., Salvadori S., Jinsmaa Y., Bryant S.D., and Lazarus L.H. J. Med. Chem. 46 (2003) 3201-3209
15. Jinsmaa Y., Miyazaki A., Fujita Y., Li T., Fujisawa Y., Shiotani K., Tsuda Y., Yokoi T., Ambo A., Sasaki Y., Bryant S.D., Lazarus L.H., and Okada Y. J. Med. Chem. 47 (2004) 2599-2610
16. Weltrowska G., Lemieux C., Chung N.N., and Schiller P.W. J. Pept. Sci. 63 (2004) 63-68
17. Vernall A.J., and Abell A.D. Org. Biomol. Chem. 2 (2004) 2555-2557
18. Zaman S., Campaner P., and Abell A.D. Bioorg. Med. Chem. 14 (2006) 8323-8331
19. Ghosh A.K., Swanson L.M., Cho H., Leshchenko S., Hussain K.A., Kay S., Walters D.E., Koh Y., and Mitsuya H. J. Med. Chem. 48 (2005) 3576-3585
20. Goudreau N., Brochu C., Cameron D.R., Duceppe J.-S., Faucher A.-M., Ferland J.-M., Grand-Maitre C., Poirier M., Simoneau B., and Tsantrizos Y.S. J. Org. Chem. 69 (2004) 6185-6201
21. Nantermet P.G., and Selnick H.G. Tetrahedron Lett. 44 (2003) 2401-2404
22. Lee K., Zhang M., Liu H., Yang D., and Burke Jr. T.R. J. Med. Chem. 46 (2003) 2621-2630
23. Chippindale A.M., Davies S.G., Iwamoto K., Parkin R.M., Smethurst C.A.P., Smith A.D., and Rodriguez-Solla H. Tetrahedron 59 (2003) 3253-3265
24. Schafmeister C.E., Po J., and Verdine G.L. J. Am. Chem. Soc. 122 (2000) 5891-5892
25. Piscopio A.D., Miller J.F., and Koch K. Tetrahedron 55 (1999) 8189-8198
26. Banerji B., Bhattacharya M., Madhu R.B., Kumar Das S., and Iqbal J. Tetrahedron Lett. 43 (2002) 6473-6477
27. Loughlin W.A., Tyndall J.D.A., Glenn M.P., and Fairlie D.P. Chem. Rev. 104 (2004) 6085-6117
28. Tyndall J.D.A., and Fairlie D.P. Curr. Med. Chem. 8 (2001) 893-907
29. Biagini S.C.G., Gibson S.E., and Keen S.P. J. Chem. Soc., Perkin Trans. 1 (1998) 2485-2499
30. Randl S., Gessler S., Wakamatsu H., and Blechert S. Synlett (2001) 430-432
31. Pernerstorfer J., Schuster M., and Blechert S. Chem. Commun. (1997) 1949-1950
32. Gibson S.E., Gibson V.C., and Keen S.P. Chem. Commun. (1997) 1107-1108
33. Poulsen S., and Bornaghi L.F. Tetrahedron Lett. 46 (2005) 7389-7392
34. Hultsch C., Berndt M., Bergmann R., and Wuest F. Appl. Radiat. Isot. 65 (2007) 818-826
35. Neumeyer J.L., Peng X., Knapp B.I., Bidlack J.M., Lazarus L.H., Salvadori S., Trapella C., and Balboni G. J. Med. Chem. 49 (2006) 5640-5643
36. Portoghese P.S. J. Med. Chem. 44 (2001) 2259-2269
37. Connon S.J., and Blechert S. Bioorg. Med. Chem. Lett. 12 (2002) 1873-1876
38. Carpino L.A., Shroff H., Triolo S.A., Mansour E.-L.M.E., Wenschuh H., and Albericio F. Tetrahedron Lett. 34 (1993) 7829-7832
39. Chatterjee A.K., Choi T.-L., Sanders D.P., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 11360-11370
40. Lebreton S., Xie X., Fergusonc D., and De Brabandera J.K. Tetrahedron 60 (2004) 9638-9647
41. Formentín P., Gimeno N., Steinke J.H.G., and Vilar R. J. Org. Chem. 70 (2005) 8235-8238
42. Forman G.S., McConnell E., Tooze R.P., van Rensburg W.J., Meyer W.H., Kirk M.M., Dwyer C.L., and Serfontein D.W. Organometallics 24 (2005) 4528-4542
43. Schmidt B. Eur. J. Org. Chem. (2004) 1865-1880
44. Lee D., Sello J.K., and Schreiber S.L. J. Am. Chem. Soc. 121 (1999) 10648-10649
45. Bressy C., and Piva O. Synlett (2003) 87-90
46. Waller A.S., and Clements J.M. Curr. Opin. Drug Discov. Devel. 5 (2002) 785-795
47. Jain R., Chen D., White R.J., Patel D.V., and Yuan Z. Curr. Med. Chem. 12 (2005) 1607-1621
48. Clements J.M., Ayscough A.P., Keavey K., and East S.P. Curr. Med. Chem.: Anti-Infect. Agents 1 (2002) 239-249
49. Hu X., Nguyen K.T., Verlinde C.L.M.J., Hol W.G.J., and Pei D. J. Med. Chem. 46 (2003) 3771-3774
50. Reddy A.S., Kumar M.S., and Reddy G.R. Tetrahedron Lett. 41 (2000) 6285-6288
51. Bruker-AXS, S. 1997-1999.
52. Sheldrick G.M. Acta Crytallogr., Sect. A A46 (1990) 467-473
53. Sheldrick G.M. SADABS (1998), University of Gottingen, Gottingen, Germany
54. Ahn Y.M., Yang K., and Georg G.I. Org. Lett. 3 (2001) 1411-1413
55. Halgren T.A. J. Comput. Chem. 20 (1999) 720-729
56. Halgren T.A. J. Comput. Chem. 17 (1996) 490-519