Helix formation in ε-amino acid oligomers

Journal of Molecular Structure: THEOCHEM

Volumn 907, Issue 1-3, 2009, Pages 109-114

  Schramm, Peter ^a   Hofmann, Hans Jörg ^a  

^a Faculty of Biosciences Pharmacy and Psychology   (Germany)

Author keywords

Amino acids; Peptides; Ab initio MO theory; Foldamers; Secondary structure

Indexed keywords

EID: 67349190517     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2009.04.033     Document Type: Article

References (73)

1. In: Hecht S., and Huc I. (Eds). Foldamers: Structure, Properties and Applications (2007), Wiley-VCH, Weinheim
2. Guichard G. In: Nielsen P.E. (Ed). Pseudopeptides in Drug Discovery (2004), Wiley-VCH, Weinheim 33
3. Seebach D., and Matthews J.L. Chem. Commun. (1997) 2015
4. Gellman S.H. Acc. Chem. Res. 31 (1998) 173
5. Kirschenbaum K., Zuckerman R.N., and Dill D.A. Curr. Opin. Struct. Biol. 9 (1999) 530
6. Stigers K.D., Soth M.J., and Nowick J.S. Curr. Opin. Chem. Biol. 3 (1999) 714
7. Smith M.D., and Fleet G.W.J. J. Pept. Sci. 5 (1999) 425
8. Hill D.J., Mio M.J., Prince R.B., Hughes T.S., and Moore J.S. Chem. Rev. 101 (2001) 3893
9. Cheng R.P., Gellman S.H., and De Grado W.F. Chem. Rev. 101 (2001) 3219
10. Venkatraman J., Shankaramma S.C., and Balaram P. Chem. Rev. 101 (2001) 3131
11. Cubberley M.S., and Iverson B.L. Curr. Opin. Chem. Biol. 5 (2001) 650
12. Martinek T.A., and Fülöp F. Eur. J. Biochem. 270 (2003) 3657
13. Seebach D., Beck A.K., and Bierbaum D.J. Chem. Biodivers. 1 (2004) 1111
14. Chatterjee S., Roy R.S., and Balaram P. J. Roy. Soc. Interf. 4 (2007) 587
15. Goodmaan C.M., Choi S., Shandler S., and DeGrado W.F. Nat. Chem. Biol. 3 (2007) 252
16. Horne W.S., and Gellman S.H. Acc. Chem. Res. 41 (2008) 1399
17. Appella D.H., Christianson L.A., Karle I.L., Powel D.R., and Gellman S.H. J. Am. Chem. Soc. 118 (1996) 13071
18. Seebach D., Overhand M., Kühnle F.N.M., Martinoni B., Oberer L., Hommel U., and Widmer H. Helv. Chim. Acta 79 (1996) 913
19. Brenner M., and Seebach D. Helv. Chim. Acta 84 (2001) 1181
20. Hintermann T., Gademann K., Jaun B., and Seebach D. Helv. Chim. Acta 81 (1998) 983
21. Hanessian S., Luo X., Schaum R., and Michnick S. J. Am. Chem. Soc. 120 (1998) 8569
22. Hanessian S., Luo X., and Schaum R. Tetrahedron Lett. 40 (1999) 4925
23. Vasudev P.G., Shamala N., Ananda K., and Balaram P. Angew. Chem. Int. Ed. 44 (2005) 4972
24. Grison C., Coutrot P., Geneve S., Didierjean C., and Marraud M. J. Org. Chem. 70 (2005) 10753
25. Szabo L., Smith B.L., McReynolds K.D., Parrill A.L., Morris E.R., and Gervay J. J. Org. Chem. 63 (1998) 1074
26. Rai R., Vasudev P.G., Ananda K., Ragothama S., Shamala N., Karle I.L., and Balaram P. Chem. Eur. J. 13 (2007) 5917
27. Vasudev P.G., Ananda K., Chatterjee S., Aravinda S., Shamala N., and Balaram P. J. Am. Chem. Soc. 129 (2007) 4039
28. Ananda K., Vasudev P.G., Sengupta A., Raja K.M.P., Shamala N., and Balaram P. J. Am. Chem. Soc. 127 (2005) 16668
29. Aravinda S., Ananda K., Shamala N., and Balaram P. Chem. Eur. J. 9 (2003) 4789
30. Roy R.S., Karle I.L., Ragothama S., and Balaram P. Proc. Natl. Acad. Sci. USA 101 (2004) 16478
31. Hayen A., Schmitt M.A., Nagassa N., Thomson K.A., and Gellman S.H. Angew. Chem. Int. Ed. 43 (2004) 505
32. De Pol S., Zorn C., Klein C.D., Zerbe O., and Reiser O. Angew. Chem. Int. Ed. 43 (2004) 511
33. Seebach D., Jaun B., Sebesta R., Mathad R.I., Flogel O., Limbach M., Sellner H., and Cottens S. Helv. Chim. Acta 89 (2006) 1801
34. Sharma G.V.M., Jadhav V.B., Ramakrishna K.V.S., Jayaprakash P., Narsimulu K., Subash V., and Kunwar A.C. J. Am. Chem. Soc. 128 (2006) 14657
35. Sharma G.V.M., Nagender P., Radha Krishna P., Jayaprakash P., Ramakrishna K.V.S., and Kunwar A.C. Angew. Chem. Int. Ed. 44 (2005) 5878
36. Srinivasulu G., Kiran Kumar S., Sharma G.V.M., and Kunwar A.C. J. Org. Chem. 71 (2006) 8395
37. Navas J.J., Alemán C., and Muñoz-Guerra S. J. Org. Chem. 61 (1996) 6849
38. Alemán C., Navas J.J., and Muñoz-Guerra S. Biopolymers 41 (1997) 721
39. Wu Y.-D., and Wang D.-P. J. Am. Chem. Soc. 120 (1998) 13485
40. Möhle K., Günther R., Thormann M., Sewald N., and Hofmann H.-J. Biopolymers 50 (1999) 167
41. Wu Y.-D., and Wang D.-P. J. Am. Chem. Soc. 121 (1999) 9352
42. Günther R., and Hofmann H.-J. J. Am. Chem. Soc. 123 (2001) 247
43. Günther R., and Hofmann H.-J. Helv. Chim. Acta 85 (2002) 2149
44. Baldauf C., Günther R., and Hofmann H.-J. Helv. Chim. Acta 86 (2003) 2573
45. Baldauf C., Günther R., and Hofmann H.-J. Angew. Chem. Int. Ed. 43 (2004) 1594
46. Beke T., Csizmadia I.G., and Perczel A. J. Comput. Chem. 25 (2004) 285
47. Baldauf C., Günther R., and Hofmann H.-J. J. Org. Chem. 69 (2004) 6214
48. Baldauf C., Günther R., and Hofmann H.-J. J. Org. Chem. 70 (2005) 5351
49. Baldauf C., Günther R., and Hofmann H.-J. Biopolymers 80 (2005) 675
50. Baldauf C., Günther R., and Hofmann H.-J. Biopolymers 84 (2006) 408
51. Baldauf C., Günther R., and Hofmann H.-J. J. Org. Chem. 71 (2006) 1200
52. Beke T., Csizmadia I.G., and Perczel A. J. Am. Chem. Soc. 128 (2006) 5158
53. Baldauf C., Günther R., and Hofmann H.-J. J. Phys. Biol. 3 (2006) S1-S9
54. Daura X., Van Gunsteren W.F., Rigo D., Jaun B., and Seebach D. Chem. Eur. J. 3 (1997) 1410
55. Daura X., Jaun B., Seebach D., Van Gunsteren W.F., and Mark A.E. J. Mol. Biol. 280 (1998) 925
56. Daura X., Van Gunsteren W.F., and Mark A.E. Proteins: Struct. Funct. Genet. 34 (1999) 269
57. Seebach D., Schreiber J.V., Abele S., Daura X., and Van Gunsteren W.F. Helv. Chim. Acta 83 (2000) 34
58. Aharoni S.M. N-Nylons (1997), J. Wiley
59. Kohan M.I. Nylon Plastics Handbook (1995), Hanser, Munich
60. Carothers W.H. Collected Papers on High Polymeric Substances. third ed. (1956), Interscience Publishers, New York
61. Banerjee A., and Balaram P. Curr. Sci. 73 (1997) 1067
62. van Well R.M., Marinelli L., Altona C., Erkelens K., Siegal G., van Raaij M., Llamas-Saiz A.L., Kessler H., Novellino E., Lavecchia A., van Boom J.H., and Overhand M. J. Am. Chem. Soc. 125 (2003) 10822
63. Hehre W.J., Ditchfield R., and Pople J.A. J. Chem. Phys. 56 (1972) 2257
64. Hariharan P.C., and Pople J.A. Chem. Phys. Lett. 66 (1972) 217
65. Becke A.D. J. Chem. Phys. 98 (1993) 5648
66. Lee C., Yang W., and Parr R.G. Phys. Rev. B37 (1988) 785
67. Cancès M.T., Mennucci B., and Tomasi J. J. Chem. Phys. 107 (1997) 3032
68. Mennucci B., and Tomasi J. J. Chem. Phys. 106 (1997) 5151
69. Mennucci B., Cancès E., and Tomasi J. J. Phys. Chem. B 101 (1997) 10506
70. Tomasi J., Mennucci B., and Cancès E. J. Mol. Struct. (Theochem) 464 (1999) 211
71. Frisch M.J., et al. Gaussian 03, Revision C.02 (2004), Gaussian Inc., Wallingford, CT
72. Banerjee A., Pramanik A., Bhattacharjya S., and Balaram P. Biopolymers 39 (1996) 769
73. Choi S.H., Guzei I.A., Spencer L.C., and Gellman S.H. J. Am. Chem. Soc. 130 (2008) 6544