Addition of a peptide fragment on an α-helical depsipeptide induces α/310-conjugated helix: Synthesis, crystal structure, and CD spectra of Boc-Leu-Leu-Ala-(Leu-Leu-Lac)3-Leu-Leu-OEt

Biopolymers

Volumn 75, Issue 3, 2004, Pages 242-254

  Oku, Hiroyuki ^a   Ohyama, Takafumi ^a   Hiroki, Akihiro ^a   Yamada, Keiichi ^a   Fukuyama, Keiichi ^b   Kawaguchi, Hiroyuki ^c   Katakai, Ryoichi ^a  

^a GUNMA UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

helix; 310 helix; Crystal structure; Depsipeptide; Lactic acid; Leucine; Liquid phase peptide synthesis; Nanomaterial; Segment condensation

Indexed keywords

CRYSTALLINE MATERIALS; SPECTRUM ANALYSIS;

DEPSIPEPTIDE; PEPTIDES;

CRYSTAL STRUCTURE;

DEPSIPEPTIDE;

ALPHA HELIX; AMINO ACID SEQUENCE; ARTICLE; CIRCULAR DICHROISM; CONFORMATION; CONJUGATION; CRYSTAL STRUCTURE; MICROCRYSTALLINE SUSPENSION; PEPTIDE SYNTHESIS;

CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; DEPSIPEPTIDES; DIPEPTIDES; HYDROGEN BONDING; LEUCINE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OLIGOPEPTIDES; PEPTIDE FRAGMENTS; PROTEIN STRUCTURE, SECONDARY; PROTONS; SOLUTIONS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 7044261949     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/bip.20117     Document Type: Article

References (93)

1. Ballard, C. E.; Yu, H.; Wang, B. Curr Med Chem 2002, 4, 471-498.
2. Pratt, W. B.; Ruddon R. W.; Ensminger, W. D.; Maybaum, J. The Anticancer Drugs; Oxford University Press: New York, 1994.
3. Shigematsu, N.; Ueda, H.; Takase, S.; Tanaka, H.; Yamamoto, K.; Tada, T. J Antibiot (Tokyo) 1994, 47, 311-314.
4. Arad, O.; Goodman, M. Biopolymers 1990, 29, 1633-1649.
5. Mammi, S.; Goodman, M. Int J Peptide Protein Res 1986, 28, 29-44.
6. Becktel, W. J.; Wouters, G.; Simmons, D. M.; Goodman, M. Macromolecules 1985, 18, 630-634.
7. Katakai, R.; Goodman, M. Macromolecules 1982, 15, 25-30.
8. Ingwall, R. T.; Goodman, M. Macromolecules 1974, 7, 598-605.
9. Gallo, E. A.; Gellman, S. H. J Am Chem Soc 1993, 115, 9774-9788.
10. Haque, T. S.; Little, J. C.; Gellman, S. H. J Am Chem Soc 1996, 118, 6975-6985.
11. Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D.; Oberer, L.; Hommel, U.; Amstutz, R.; Widmer, H. Helv Chim Acta 1996, 79, 2043-2066.
12. Seebach, D.; Mahajan, Y. R.; Senthilkumar, R.; Rueping, M.; Jaun, B. Chem Commun 2002, 15, 1598-1599.
13. Peggion, C.; Barazza, A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Villa, M.; Tomasini, C.; Mayrhofer, H.; Pochlauer, P.; Kaptein, B.; Broxterman, Q. B. J Chem Soc Perkin 2 2002, 3, 644-651.
14. Karle, I. L.; Das, C.; Balaram, P. Biopolymers 2001, 59, 276-289.
15. Aravinda, S.; Shamala, N.; Das, C.; Balaram, P. Biopolymers 2002, 64, 255-267.
16. Katakai, R. J Chem Soc, Chem Commun 1988, 1229-1230.
17. Katakai, R.; Kobayashi, K.; Yonezawa, N.; Yoshida, M. Biopolymers 1995, 38, 285-290.
18. Ohyama, T.; Oku, H.; Maekawa, Y.; Yoshida, M.; Katakai, R. Biopolymers 2000, 38, 285-290.
19. Ohyama, T.; Oku, H.; Yoshida, M.; Katakai, R. Biopolymers 2001, 58, 636-642.
20. Oku, H.; Yamada, K.; Katakai, R. Acta Cryst 2003, E59, o1130-o1132.
21. Oku, H.; Shichiri, K.; Yamada, K.; Katakai, R. Acta Cryst 2003, E59, o1413-o1415.
22. Oku, H.; Yamada, K.; Katakai, R. Acta Cryst 2003, E53, o1581-o1583.
23. Oku, H.; Suda, T.; Yamada, K.; Katakai, R. Acta Cryst 2004, E60, o720-o721.
24. Katakai, R.; Kobayashi, K.; Yamada, K.; Oku, H.; Emori, N. Biopolymers 2004, 73, 641-644.
25. Ohyama, T., Hiroki, A.; Kobayashi, K.; Katakai, R. In Peptide Chemistry 1996; Kitada, C., Ed.; Protein Reserach Foundation: Osaka, 1997; pp 365-368.
26. Ohyama, T.; Hiroki, A.; Kobayashi, K.; Wakamatsu, K.; Katakai, R. In Peptide Science - Present and Future; Shimonishi, Y., Ed.; Kluwer Academic Publishers: Dordrecht, 1999; pp 284-285.
27. Ohyama, T.; Oku, H.; Katakai, R. In Peptide Science 1999; Fujii, N., Ed.; Protein Research Foundation: Osaka, 2000; pp 287-290.
28. Oku, H.; Tetsuka, Y; Ohyama, T.; Katakai, R. In Peptide Science 1999; Fujii, N., Ed.; Protein Research Foundation: Osaka, 2000; pp 291-294.
29. Yasuno, K.; Oku, H.; Yamada, K.; Katakai, R. In Peptide Science 2000; Fujii, N. Ed.; Protein Research Foundation: Osaka, 2001; pp 297-300.
30. Taira, T.; Oku, H.; Yamada, K.; Katakai, R. In Peptide Science 2003; Ueki, M. Ed.; Protein Research Foundation: Osaka, 2004; pp 177-180.
31. Blankenship, J. W.; Balambika, R.; Dawson, P. E. Biochemistry 2002, 41, 15676-15684.
32. Rijkers, D. T. S.; Hoppener, J. W. M.; Posthuma, G.; Lips, C. J. M.; Liskamp, R. M. J. Chem Eur J 2002, 8, 4285-4291.
33. Ellman, J. A.; Mendel, D.; Schultz, P. G. Science 1992, 255, 197-200.
34. Shin, I.; Ting, A. Y.; Schultz, P. G. J Am Chem Soc 1997, 119, 12667-12668.
35. Chapman, E.; Thorson, J. S.; Schultz, P. G. J Am Chem Soc 1997, 119, 7151-7152.
36. Koh, J. T.; Cornish, V. W.; Schultz, P. G. Biochemistry 1997, 36, 11314-11322.
37. Groeger, C.; Wenzel, H. R.; Tschesche, H. Int J Peptide Protein Res 1994, 44, 166-172.
38. Lu, W.; Qasim, M. A.; Laskowski, M., Jr.; Kent, S. B. H. Biochemistry 1990, 36, 673-679.
39. Shirahama, H; Umemoto, K; Yasuda, H. J Biomater Sci Polym Ed 1999, 10, 621-39.
40. Shirahama, H.; Nagasawa, M.; Umemoto, K.; Yasuda, H. Kobunshi Ronbunshu 1998, 55, 359-366.
41. Ohya Y., Matsunami H., Yamabe E., Ouchi T. J Biomed Mater Res 2003, 65A, 79-88.
42. Yoshida, M.; Asano, M.; Kumakura, M.; Katakai, R.; Mashimo, T.; Yuasa, H.; Imai, K.; Yamanaka, H. J Biomed Mater Res 1990, 24, 1173-1184.
43. Ohya, Y.; Matsunami, H.; Ouchi, T. J Biomater Sci Polym Ed. 2004, 15, 111-123.
44. Ohya, Y.; Matsunami, H.; Yamabe, E.; Ouchi, T. J Biomed Mater Res 2003, 65A, 79-88.
45. Miller, R.; Gallo, S. M.; Khalak, H. G.; Weeks, M. C. J Appl Cryst 1994, 27, 613-621.
46. Burla, M. C.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; Giacovazzo, C.; Polidori, G.; Spagna, R. J Appl Cryst 2003, 36, 1103.
47. Walker, N.; Stuart, D. Acta Cryst A 1983, 39, 158-166.
48. α-Helix, (φ,φ) = (-57°, -47°): Arnott, S.; Wonacott, A. J. J Mol Biol 1966, 21, 371-383.
49. 10-helix, (φ,φ) = (-60°, -30°): Toniolo, C.; Benedetti, E. Trends Biochem Sci 1991, 16, 350-353.
50. 10-Helices in proteins, (φ,φ) = (-71°, -18°): Barlow, D. J.; Thornton, J. M. J Mol Biol 1988, 201, 601-619.
51. IUPAC-IUB Commission on Biochemical Nomenclature J Mol Biol 1970, 52, 1-17.
52. Janin, J.; Wodak, S.; Levitt, M.; Maigret, B. J Mol Biol 1978, 125, 357-386.
53. Benedetti, E.; Morelli, G.; Nemethy, G.; Scheraga, H. A. Int J Peptide Protein Res 1983, 22, 1-15.
54. Ponnuswamy, P. K.; Sasisekaran, V. Int J Peptide Protein Res 1971, 3, 9-18.
55. Ramakrishnan, C.; Prasad, N. Int J Protein Res 1971, 3, 209-231.
56. Stickle, D. F.; Presta, L. G.; Dill, K. A.; Rose, G. D. J Mol Biol 1992, 226, 1143-1159.
57. Toniolo, C. CRC Crit Rev Biochem 1980, 9, 1-44.
58. Datta, S.; Shamala, N.; Banerjee, A.; Balaram, P. J Peptide Res 1997, 49, 604-611.
59. Tinoco, I., Jr.; Woody, R. W.; Bradley, D. F. J Chem Phys 1963, 38, 1317-1325.
60. Katakai, R.; Iizuka, Y. J Am Chem Soc 1984, 106, 5715-5718.
61. Manning, M. C.; Woody, R. W. Biopolymers 1991, 31, 569-586.
62. Fasman, G. D., Ed. Circular Dichroism and the Conformational Analysis of Biomolecules; Plenum Press: New York, 1996.
63. Holworth, G.; Doty, P. J. J Am Chem Soc 1965, 87, 218-228.
64. Greenfield, N.; Fasman, G. D. Biochemistry 1969, 8, 4108-4116.
65. Goodman, M.; Naider, P.; Rupp, R. Bioorg Chem 1971, 1, 310-328.
66. Becker, J. M.; Naider, F. Biopolymers 1974, 13, 1747-1750.
67. Bonora, G. M.; Toniolo, C. Biopolymers 1974, 13, 1067-1078.
68. Bosnich, B.; Harrowfield, J. MacB. J Am Chem Soc 1972, 94, 3425.
69. Hu, H.-Y.; Li, Q.; Cheng, H.-C.; Du, H.-N. Biopolymers 2000, 62, 15-21.
70. Formaggio, F.; Crisma, M.; Toniolo, C.; Kamphuis, J. Biopolymers 1996, 38, 301-304.
71. Polese, A.; Formaggio, F.; Crisma, M.; Valle, G.; Toniolo, C.; Bonora, G. M.; Broxterman, Q. B.; Kamphuis, J. Chem Eur J 1996, 2, 1104-1111.
72. Inai, Y.; Sakakura, Y.; Hirabayashi, T. Polym J 1998, 30, 828-832.
73. Kuroda, R. In Circular Dichroism, 2nd ed.; Berova, N.; Nakanishi, K., Woody, R. W., Eds.; Wiley-VCH: New York, 2000; pp 159-184.
74. Kuroda, R.; Saito, Y. Bull Chem Soc Jpn 1976, 49, 433-436.
75. Toda, F.; Miyamoto, H.; Kanemoto, K. J Org Chem 1996, 61, 6490-6491.
76. Toda, F.; Miyamoto, H.; Shiro, K.; Kuroda, R.; Nagami, F. J Am Chem Soc 1996, 118, 11315-11316.
77. Toniolo, C.; Polese, A.; Formaggio, F.; Crisma, M.; Kamphuis, J. J Am Chem Soc 1996, 118, 2744-2745.
78. Sudha, T. S.; Vijayakumar, E. K. S.; Balaram, P. Int J Pept Protein Res 1983, 22, 464-468.
79. Katakai, R. J Chem Soc Perkin 1 1979, 905-909.
80. Katakai, R.; Nakayama, Y. Polymer 1977, 18, 755-758.
81. Katakai, R.; Nakayama, Y. J Chem Soc Chem Commun 1977, 924-925.
82. Katakai, R.; Nakayama, Y. J Chem Soc Chem Commun 1977, 805-806.
83. Katakai, R. J Chem Soc Perkin 1, 1977, 1193-1196.
84. Katakai, R. J Am Chem Soc 1977, 99, 232-234.
85. Toniolo, C. Biopolymers 1977, 16, 219-224.
86. Palumbo, M.; Rin, S. D.; Bonora, G. M.; Toniolo, C. Macromol Chem 1976, 177, 1477-1492.
87. Balcerski, J. S.; Pysh, E. S.; Bonora, G. M.; Toniolo, C. J Am Chem Soc 1976, 98, 3470-3473.
88. Fujie, A.; Komoto, T.; Oya, M.; Kawai, T. Makromol Chem 1973, 169, 301-321.
89. Manuscript in preparation.
90. PDB code: 1QRE (Thrl94-Glu211). Iverson, T. M.; Alber, B. E.; Kisker, C.; Ferry, J. G.; Rees, D. C. Biochemistry, 2000, 39, 9222-9231.
91. PDB code: 1QQS and 1DFV (Thr145-Leu159). Goetz, D. H.; Willie, S. T.; Armen, R. S.; Bratt, T.; Borregaard, N.; Strong, R. K. Biochemistry 2000, 39, 1935-1941.
92. PDB code: 1AYZ (Asp101-Phe113, Asn123-Met153). Worthylake, D. K.; Prakash, S.; Prakash, L.; Hill, C. P. J Biol Chem 1998, 273, 6271-6276.
93. PDB code: 1GNK (Leu13-Ser22, Glu69-Tyr82). Xu, Y.; Cheah, E.; Carr, P. D.; van Heeswijk, W. C.; Westerhoff, H. V.; Vasudevan, S. G.; Ollis, D. L. J Mol Biol 1998, 282, 149-165.