Expanding the peptide β -turn in α γ hybrid sequences: 12 atom hydrogen bonded helical and hairpin turns

Journal of the American Chemical Society

Volumn 131, Issue 16, 2009, Pages 5956-5965

  Chatterjee, Sunanda ^a   Vasudev, Prema G ^a   Raghothama, Srinivasarao ^a   Ramakrishnan, Chandrasekharan ^a   Shamala, Narayanaswamy ^a   Balaram, Padmanabhan ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1-FORMS; AMINO ACID RESIDUES; GAUCHE CONFORMATION; HAIRPIN CONFORMATION; HAIRPIN STRUCTURES; HYBRID PEPTIDES; HYBRID SEQUENCES; HYDROGEN-BONDED STRUCTURES; OCTAPEPTIDES; THEORETICAL CALCULATIONS; TORSION ANGLE;

AMINATION; AMINO ACIDS; HYDROGEN; HYDROGEN BONDS; METHANOL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; PEPTIDES; POLYPEPTIDES;

AMINES;

AMYLOID BETA PROTEIN; CARBON; GABAPENTIN; HYDROGEN; METHANOL; 4 AMINOBUTYRIC ACID; AMINE; CYCLOHEXANECARBOXYLIC ACID DERIVATIVE; PEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; CONFORMATION; CRYSTAL STRUCTURE; HYDROGEN BOND; PEPTIDE SYNTHESIS; SOLID STATE; STEREOCHEMISTRY; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; PROTEIN CONFORMATION; PROTEIN SECONDARY STRUCTURE; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINES; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; CYCLOHEXANECARBOXYLIC ACIDS; GAMMA-AMINOBUTYRIC ACID; HYDROGEN BONDING; MODELS, MOLECULAR; PEPTIDES; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; STEREOISOMERISM;

EID: 70249130943     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja900618h     Document Type: Article

References (70)

1. For reviews. see: (a) Seebach. D. Beck A. K. Bierbaum. D. J. Chem. Biodiversitv 2004. 1. 1111-1239.
2. (b) Cheng R. P. Gellman S. H. DeGrado W. F. Chem. Rev. 2001, 101, 3219-3232.
3. (c) Goodman C. M. Choi, S. Shandler S. DeGrado. W. F Nay. Chem. Biol. 2007. 3, 252-262.
4. (d) Gellman. S. H. Acc. Chem. Res. 1998, 31, 173-180.
5. (e) Home W. S. Gellman S. H. Acc. Chem. Res. 2008. 41, 1399-1408.
6. For representative references. see: (a) Roy R. S. Balaram. P. J. Peptide Res. 2004, 63, 279-289.
7. (b) Chatterjee. S. Roy. R. S. Balaram. P. J. R. Soc. Interface 2006, 4, 587-606.
8. (c) Choi S. H. Guzei I. A. Gellman S. H. J Am Chem. Soc. 2007, 129, 13780-13781.
9. (d) Home, W. S. Price J. L. Keck J. L. Gellman S. H. 6J Am. Chem. Soc. 2007. 129. 4178-4180.
10. (e) De Pol S. Zorn C. Klein C. D. Zerbe O. Reiser O. Angew. Chem., Int. Ed. 2004, 43, 511-514.
11. (t) Seebach D. Jaun. B. Sebesta R. Mathad. R. I. Flogel O. Limbach, M. Sellner H. Cottens S. Helv. Chim. Acta 2006, 89, 1801-1825.
12. (g) Srinivasulu G. Kumar S. K. Sharma G. V. M. Kunwar A. C. J. Org. Chem. 2006, 71, 8395-8400.
13. (h) Baldauf C. Gunther R. Hofmann H. J. Biopolymers 2006. 84, 408-413.
14. (i) Baldauf C. Gunther R. Hofmann H. J. J. Org Chem. 2006, 71, 1200-1208.
15. (a) Seebach D. Overhand M. Kiihnle F. N. M. Martinoni B. Helv. Chim. Acta 1996, 79, 913-941.
16. (b) Appella. D. H. Christianson L. A. Karle, I. L. Powell. D. R. Gellman S. H. J. Am Chem. Soc. 1996, 118, 13071-13072.
17. (c) Appella D. H. Christianson L. A. Klem D. A. Powell D. R. Huang X. Barchi. J. J., Jr. Gellman. S. H. Nature (London) 1997, 387, 381-384.
18. (d) Appella D. H. Christianson L. A. Klein D. A. Richards M. R. Powell. D. R. Gellman. S. H. J. Am. Chem. Soc. 1999, 121, 7574-7581.
19. (a) Seebach D. Gardiner J. Acc. Chem. Res., 2008. 41, 1366-1375.
20. (b) Schmitt M. A. Weisblum. B. Gellman S. H. J Am. Chem. Soc. 2007, 129, 417-428.
21. (c) Stephens O. Kim S. Welch B. D. Hodsdon M. E. Kay M. S. Schepartz A. J. Am. Chem. Soc. 2005, 127, 13126-13127.
22. (d) Kritzer J. S. Stephens O. M. Guarracino D. A. Reznik S. K. Schepartz A. Bioorg. Med. Chem. 2005, 13, 11-16.
23. Helices: (a) Karle. I. L. Pramanik A. Banerjee. A. Battachaijva. S. Balaram P. J. Am. Chem. Soc. 1997, 119, 9087-9095.
24. (b) Roy, R. S. Karle, I. L. Raghothama S. Balaram P. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 16478-16482.
25. (c) Ananda. K. Vasudev P. G. Sengupta. A. Raja K. M. P. Shamala N. Balaram P. J. Am. Chem. Soc. 2005, 127, 16668-16674.
26. (d) Choi S. H. Guzei, l. A. Spencer L. C. Gellman S. H. J Am. Chem. Soc. 2008, 130, 6544-6550β -hairpins
27. (e) Karle I. L. Gopi H. N. Balaram P. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 5160-5164.
28. (f) Karle I. L. Gopi H. N; Balaram P. Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 3716-3719.
29. (g) Roy R. S. Gopi H. N. Raghothama S. Karle I. L. Balaram P. Chem.-Eur. J. 2006. 12. 295-3302.
30. (h) Rai R. Vasudev P. G. Ananda K. Raghothama S. Shamala. N. Karle I. L. Balaram. P. Chem.-Eur. J. 2007, 13, 5917-5926.
31. (a) Prasad B. V. V. Balaram P. CRC Crit. Rev. Biochem. 1984, 16, 307-347.
32. (b) Karle I. L. Balaram P. Biochemistry 1990, 29, 6747-6756.
33. (c) Aravinda S. Shamala N. Roy R. S. Balaram P. Proc. Indian Acad. Sci. (Chem. Sci.) 2003. 115, 373-400.
34. (d) Toniolo C. Benedetti E. Macromolecules 1991, 24, 4004-4009.
35. (e) Crisma M. Formaggio F. Toniolo C. Moretto. A. Biopolxmers (Peptide Sci.) 2006, 84, 3-12.
36. (t) Bolin K. A. Millhauser G. l. Acc. Chem. Res. 1999, 32, 1027-1033.
37. (g) Marshall. G. R. Bosshard H. E. Circ. Res. 1972, 30/31, 143.
38. (a) Seebach D. Abele S. Sifferlen T. Hänggi M. Gruner S. Seiler P. Helv. Chim. Acta 1998, 81, 2218-2243.
39. (b) Vasudev. P. G. Rai. R. Shamala. N. Balaram. P. Biopolymers (Pept. Sci.) 2008. 90, 138-150.
40. (a) Ananda K. Aravinda, S. Vasudev P. G. Raja K. M. P. Sivaramakrishnan H. Nagarajan K. Shamala. N. Balaram P. Curr. Sci, 2003, 85, 1002-1011.
41. (b) Vasudev P. G. Ananda K. Chatterjee S. Aravinda S. Shamala N. Balaram P. J. Am. Chem. Soc. 2007, 129, 4039-4048.
42. (c) Chatterjee S. Vasudev P. G. Ananda K. Raghothama. S. Shamala. N. Balaram P. J. Org Chem. 2008. 73, 6595-6606.
43. (d) Vasudev. P. G. Chatterjee S. Ananda K. Shamala N. Angew. Chem., Int. Ed. 2008, 47, 6430-6432.
44. (a) Venkatachalam C. M. Bwpolymers 1968, 6, 1425-1436.
45. (b) Ramachandran G. N. Sasisekharan. V. Adv. Protein Chem. 1968, 23, 284-438.
46. (c) Paul P. K. C. Ramaknshnan C. J. Biomol. Struct. Dyn. 1985, 2, 879-898.
47. Schneider T. R. Sheldrick. G. M. Acta Crystallogr. 2002. D58, 1772-1779.
48. Peptides: Synthesis, structure and applications Gutte B. Ed.; Academic Press: New York, 1995.
49. Sheldrick G. M. SHELXL-97, A program for crystal structure refinement; University of Göttingen: Göttingen, 1997.
50. Corey R. B. Pauling L. Proc. R. Soc. London 1953, B141, 10-20.
51. Ramachandran G. N. Ramakrishnan. C. Sasisekharan V. J. Mol Biol. 1963, 7, 95-99.
52. (a) Donohue J. Proc. Natl. Acad. Sci. U. S. A. 1953, 39, 470-478.
53. (b) Toniolo C. Benedetti E. Trends Biochem. Sci. 1991, 16, 350-353.
54. Aravinda S. Shamala N. Balaram P. Chem Biodiversity 2008, 5, 1238-1262.
55. Mahalakshmi. R. Raghothama S. Balaram. P. J. Am. Chem. Soc. 2006, 128, 1125-1138.
56. (a) Ramachandran G. N. Lakshminarayanan A. V. Balasubramanian R. Tegoni G. Biochim. Biophys. Acta 1970, 221, 165-181.
57. (b) Lewis P. N. Momanv F. A. Scheraga H. A. Biochim. Biophvs. Acta 1973, 303, 211-229.'
58. (c) Wilmot C. M. Thornton J. M. J. Mol. Biol. 1988, 203. 221-232.
59. (d) Rose G. D. Gierasch L. M. Smith J. A. Adv Protein Cham. 1985, 37, 1-109.
60. (e) Sibanda. B. L. Thornton J. M. Nature (London) 1985, 316, 170-174.
61. (f) Gunasekaran K. Gomathi L. Ramakrishnan C. Chandrasekhar. J. Balaram P. J. Mol. Biol. 1998, 284, 1505-1516.
62. Venkataraman J. Shankaramma. S. C. Balaram. P. Chem. Rev. 2001. 101, 3131-3152.
63. (a) Gellman S. H. Curr. Opin. Chem. Biol. 1998. 2, 717-725.
64. (b) Hughes R. M. Waters. M. L. Curr: Opin. Struct. Biol. 2006, 16, 514-524.
65. (c) Robinson J. A. Acc. Chem. Res. 2008, 41, 1278-1288.
66. For a definition of torsion angle nomenclature in backbone homologated amino acids, see: Banerjee A. Balaram P. Curr. Sci. 1997, 73, 1067-1077, and ref lb.
67. 7 hydrogen bonds (γ -turns) in α amino acid peptides, see: (a) Nemethy G. Printz. M. P. Macromolecules 1972. 5, 755-758.
68. (b) Milner-White E. J. Ross B. M. Ismail R. Belhady- Mostafa. K. Poet. R. J. Mol. Biol. 1988, 204, 777-782.
69. (c) Milner- White E. J. J. Mol. Biol. 1990, 216, 385-397.
70. (d) Matthews B. W. Macromolecules 1972, 5, 818-819.