The urea-dipeptides show stronger H-bonding propensity to nucleate β-sheetlike assembly than natural sequence

Tetrahedron

Volumn 65, Issue 39, 2009, Pages 8269-8276

  Ke, Damei ^a,b   Zhan, Chuanlang ^a   Li, Xiao ^a,b   Li, Alexander D Q ^c   Yao, Jiannian ^a  

^a PEKING UNIVERSITY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE DERIVATIVE; UREA DERIVATIVE;

AMINO ACID SEQUENCE; ARTICLE; BETA SHEET; CIRCULAR DICHROISM; HYDROGEN BOND; PEPTIDE ANALYSIS; PRIORITY JOURNAL; PROTEIN ASSEMBLY; PROTEIN STRUCTURE; X RAY DIFFRACTION;

EID: 69049119158     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.07.048     Document Type: Article

References (52)

1. Zhao X., Chang Y.-L., Fowler F.W., and Lauher J.W. J. Am. Chem. Soc. 112 (1990) 6627-6634
2. Cbang Y.-L., West M.-A., Fowler F.W., and Lauher J.W. J. Am. Chem. Soc. 115 (1993) 5991-6000
3. Coe S., Kane J.J., Nguyen T.L., Toledo L.M., Wininger E., Fowler F.W., and Lauher J.W. J. Am. Chem. Soc. 119 (1997) 86-93
4. Castellano R.K., Kim B.H., and Rebek Jr. J. J. Am. Chem. Soc. 119 (1997) 12671-12672
5. Rincon A.M., Prados P., and de Mendoza J. J. Am. Chem. Soc. 123 (2001) 3493-3498
6. Carroll J.B., Gray M., McMenimen K.A., Hamilton D.G., and Rotello V.M. Org. Lett. 5 (2003) 3177-3180
7. Vos M.R.J., Jardl G.E., Pallas A.L., Breurken M., van Asselen O.L.J., Bomans P.H.H., Leclere P.E.L.G., Frederik P.M., Nolte R.J.M., and Sommerdijk N.A.J.M. J. Am. Chem. Soc. 127 (2005) 16768-16769
8. Wang C., Zhang D., and Zhu D. J. Am. Chem. Soc. 127 (2005) 16372-16373
9. Inokuma T., Hoashi Y., and Takemoto Y. J. Am. Chem. Soc. 128 (2006) 9413-9419
10. Li H.-Y., Jin Y., Morisseau C., Hammock B.D., and Long Y.-Q. Bioorg. Med. Chem. 14 (2006) 6586-6592
11. Morisseau C., Goodrow M.H., Newman J.W., Wheelock C.E., Dowdy D.L., and Hammock B.D. Biochem. Pharmacol. 63 (2002) 1599-1608
12. Morisseau C., Goodrow M.H., Dowdy D., Zheng J., Greene J.F., Sanborn J.R., and Hammock B.D. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 8849-8854
13. Nowick J.S., Powell N.A., Martinez E.J., Smith E.M., and Noronha G. J. Org. Chem. 57 (1992) 3763-3765
14. Nowick J.S., Abdi M., Bellamo K.A., Love J.A., Martinez E.J., Noronha G., Smith E.M., and Ziller J.W. J. Am. Chem. Soc. 117 (1995) 89-99
15. Nowick J.S. Acc. Chem. Res. 32 (1999) 287-296
16. Burgess K., Linthicum D.S., and Shin H. Angew. Chem., Int. Ed. Engl. 34 (1995) 907-909
17. Burgess K., Ibarzo J., Linthicum D.S., Russell D.H., Shin H., Shitankoon A., Totani R., and Zhang A.J. J. Am. Chem. Soc. 119 (1997) 1556-1564
18. Kim J.M., Bi Y., Parkoff S.J., and Schultz P.G. Tetrahedron Lett. 37 (1996) 5305-5308
19. Kim J.M., Wilson T.E., Norman T.C., and Schultz P.G. Tetrahedron Lett. 37 (1996) 5309-5312
20. He J.X., Cody W.L., and Doherty A.M. J. Org. Chem. 60 (1995) 8262-8266
21. Llinàs-Brunet M., Moss N., Scouten E., Liuzzi M., and Déziel R. Bioorg. Med. Chem. Lett. 6 (1996) 2881-2886
22. Ranganathan D., Kurur S., Madhusudanan K.P., and Karle I.L. Tetrahedron Lett. 38 (1997) 4659-4662
23. Decicco C.P., Seng J.L., Kennedy K.E., Covington M.B., Welch P.K., Arner E.C., Magolda R.L., and Nelson D.J. Bioorg. Med. Chem. Lett. 7 (1997) 2331-2336
24. Konda Y., Takahashi Y., Mita H., Takeda K., and Harigaya Y. Chem. Lett. (1997) 345-346
25. Kruijtzer J.A.W., Lefeber D.J., and Liskamp R.M.J. Tetrahedron Lett. 36 (1995) 2583-2586
26. Boeijen A., and Liskamp R.M.J. Eur. J. Org. Chem. (1999) 2127-2135
27. Semetey V., Rognan D., Hemmerlin C., Graff R., Briand J.-P., Marraud M., and Guichard G. Angew. Chem., Int. Ed. 41 (2002) 1893-1895
28. Violette A., Averlant-Petit M.C., Semetey V., Hemmerlin C., Casimir R., Graff R., Marraud M., Briand J.-P., Rognan D., and Guichard G. J. Am. Chem. Soc. 127 (2005) 2156-2164
29. Sureshbabu V.V., Patil B.S., and Venkataramanarao R. J. Org. Chem. 71 (2006) 7697-7705
30. Semetey V., Didierjean C., Briand J.-P., Aubry A., and Guichard G. Angew. Chem., Int. Ed. 41 (2002) 1895-1898
31. Stefanelli S., Cavaletti L., Sarubbi E., Ragg E., Colombo L., and Selva E. J. Antibiot. 48 (1995) 332-334
32. Sarubbi E., Seneci P.F., Angelastro M.R., Peet N.P., Denaro M., and Islam K. FEBS Lett. 319 (1993) 253-256
33. Watanbe T., and Murao S. Agric. Biol. Chem. 43 (1979) 243-250
34. Stella S., Saddler G.S., Sarubb E., Colombo S., Stefanelli M., Denaro M., and Selva E. J. Antibiot. 44 (1991) 1019-1022
35. Zhang X., Rodrigues J., Evans L., Hinkle B., Ballantyne L., and Pena M. J. Org. Chem. 62 (1997) 6420-6423
36. Page P., Bradley M., Walters I., and Teague S. J. Org. Chem. 64 (1999) 794-799
37. Schmidt E.W., Harper M.K., and Faulkner D.J. J. Nat. Prod. 60 (1997) 779-782
38. Reshef V., and Carmeli S. J. Nat. Prod. 65 (2002) 1187-1189
39. Mueller D., Krick A., Kehraus S., Mehner C., Hart M., Kuepper F.C., Saxena K., Prinz H., Schwalbe H., Janning P., Waldmann H., and Koenig G.M. J. Med. Chem. 49 (2006) 4871-4878
40. Robinson S.J., Tenney K., Yee D.F., Martinez L., Media J.E., Valeriote F.A., Van Soest R.W.M., and Crews P. J. Nat. Prod. 70 (2007) 1002-1009
41. Dales N.A., Bohacek R.S., Satyshur K.A., and Rich D.H. Org. Lett. 3 (2001) 2313-2316
42. Slater M.J., Amphlett E.M., Andrews D.M., Bamborough P., Carey S.J., Johnson M.R., Jones P.S., Mills G., Parry N.R., Somers D.O.'N., Stewart A.J., and Skarzynski T. Org. Lett. 5 (2003) 4627-4630
43. Kaneto R., Chiba H., Dobashi K., Kojima I., Saki K., Shibamoto N., Nishida H., Okamoto R., Akagawa H., and Mizuno S. J. Antibiot. 46 (1993) 1622-1624
44. Malcolm B.A., Lowe C., Shechosky S., Mckay R.T., Yang C.C., Shah V.J., Simon R.J., Vederas J.C., and Santi D.V. Biochemistry 34 (1995) 8172-8179
45. Ke D., Zhan C., Li X., Li A.D.Q., and Yao J. Synlett (2009) 1506-1510
46. Ke D., Zhan C., Li X., Wang Y., Li A.D.Q., and Yao J. Tetrahedron Lett. 50 (2009) 3926-3928
47. Pistia-Brueggeman G., and Hollingsworth R.I. Carbohydr. Res. 338 (2003) 455-458
48. Smith L.J., Bolin K.A., Schwalbe H., MacArthur M.W., Thornton J.M., and Dobson C.M. J. Mol. Biol. 255 (1996) 494-506
49. Wishart D.S., Sykes B.D., and Richards F.M. Biochemistry 31 (1992) 1647-1651
50. Kelly S.M., Jess T.J., and Price N.C. Biochim. Biophys. Acta 1751 (2005) 119-139
51. Ke D., Zhan C., Li X., Wang X., Zeng Y., and Yao J. J. Colloid Interface Sci. 337 (2009) 54-60
52. Makin O.S., and Serpell L.C. Fibre Diffr. Rev. 12 (2004) 29-35