Resonance Raman examination of the electronic excited states of glycylglycine and other dipeptides: Observation of a carboxylate → amide charge transfer transition

Journal of the American Chemical Society

Volumn 118, Issue 40, 1996, Pages 9705-9715

  Chen, X G ^a,b   Li, Pusheng ^b   Holtz, Janet S W ^b   Chi, Zhenhuan ^b   Pajcini, Vasil ^b   Asher, Sanford A ^b   Kelly, Lisa A ^c  

^a EUNICE KENNEDY SHRIVER NATIONAL INSTITUTE OF CHILD HEALTH AND HUMAN DEVELOPMENT   (United States)

^b UNIVERSITY OF PITTSBURGH   (United States)

^c BROOKHAVEN NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; AQUEOUS SOLUTIONS; CHARGE TRANSFER; ELECTRON ENERGY LEVELS; RAMAN SPECTROSCOPY;

AMIDES; CARBOXYLATES; CHARGE TRANSFER TRANSITIONS; DIPEPTIDES; ELECTRON TRANSFER; GLYCYLGLYCINE; RAMAN DEPOLARIZATION RATIOS;

POLYPEPTIDES;

DIPEPTIDE; GLYCYLGLYCINE;

ARTICLE; MOLECULAR DYNAMICS; PROTEIN ANALYSIS; PROTEIN STRUCTURE; RAMAN SPECTROMETRY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0030577123     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960421+     Document Type: Article

References (64)

1. (a) Shang, H. S.; Head-Gordon, T. J. Am. Chem. Soc. 1994, 116, 1528.
2. (b) Head-Gordon, T.; Head-Gordon, M.; Frisch, M. J.; Brooks, C. L., III; Pople, J. A. J. Am. Chem. Soc. 1991, 113, 5989.
3. Ryan, J. A.; Whitten, J. L. J. Am. Chem. Soc. 1972, 94, 2396.
4. Petke, J. D. J. Chem. Phys. 1990, 93, 2561.
5. Pellegrini, M.; Doniach, S. J. Chem. Phys. 1995, 103, 2696.
6. Stites W. E.; Pranata, J. Protein Struct. Funct. Gen. 1995 22, 132.
7. Li, Y.; Garrell, R. L.; Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5895.
8. Robin, M. B. Higher Excited States of Polyatomic Molecules; Academic Press: Orlando, 1975; Vol. II.
9. Hill, R. R.; Coyle, J. D.; Birch, D.; Dawe, E.; Jeffs, G. E.; Randall, D.; Stec, I.; Stevenson, T. M. J. Am. Chem. Soc. 1991, 113, 1805.
10. (a) Krimm, S.; Song, S.; Asher, S. A. J. Am. Chem. Soc. 1989, 111, 4290.
11. (b) Song, S.; Asher, A. S.; Krimm, S.; Shaw, K. D. J. Am. Chem. Soc. 1991, 113, 1155.
12. (c) Song, S.; Asher, S. A. J. Am. Chem. Soc. 1989, 111, 4295.
13. (a) Wang, Y.; Purrello, R.; Georgiou, S.; Spiro, T. G. J. Am. Chem. Soc. 1991, 113, 6359.
14. (b) Wang, Y.; Purrello, R.; Spiro, T. G. J. Am. Chem. Soc. 1989, 111, 8274.
15. Clark, L. B. J. Am. Chem. Soc. 1995, 117, 7974.
16. Klapstein, D.; Olivato, P. R.; Oike, F.; Martins, M. A. P.; Rittner, R. Can. J. Spectrosc. 1988, 33, 161.
17. Miyazawa, M.; Kyogoku, Y.; Sugeta, H. Spectrochim. Acta 1994, 50A, 1505.
18. (a) Biswas, A. B.; Hughes, E. W.; Sharma, B. D.; Wilson, J. N. Acta Crystallogr. 1968, B24, 40.
19. (b) Hughes, E. W Acta Crystallogr. 1968, B24, 1128.
20. Freeman, H. C.; Paul, G. L. Acta Crystallogr. 1970, B26, 925.
21. Pajcini, V.; Chen, X. G.; Bormett, R. W.; Geib, S. J.; Li, P.; Asher, S. A.; Lidiak, E. G. J. Am. Chem. Soc. 1996, 118, 9716 (following paper in this issue).
22. Koetzle, T. F.; Hamilton, W. C. Acta Crystallogr. 1972, B28, 2083.
23. Beeson, C.; Dix, T. A. J. Chem. Soc., Perkin. Trans. 2 1991, 1913.
24. (a) Chen, X. G.; Asher, S. A.; Schweitzer-Stenner, R.; Mirkin, N. G.; Krimm, S. J. Am. Chem. Soc. 1995, 117, 2884.
25. (b) Chen, X. G.; Schweitzer-Stenner, R.; Asher, S. A.; Mirkin, N. G.; Krimm, S. J. Phys. Chem. 1995, 99, 3074.
26. (a) Hudson, B. S. In press.
27. (b) Mayne, L. C.; Hudson, B. J. Phys. Chem. 1991, 95, 2962.
28. Scheliman, J. A.; Becktel, W. J. Biopolymers 1983, 22, 171.
29. Tinoco, I., Jr.; Cantor, C. R. Methods Biochem. Anal. 1970, 18, 81.
30. Wasielewski, M. R. In Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part A, p 161.
31. Isied, S. S. Electron Transfer Inorg. Org. Biol. Syst. 1991, 228, 229.
32. Weinkauf, R.; Schanen, P.; Yang, D.; Soukara, S.; Schlag, E. W. J. Phys. Chem. 1995, 99, 11255.
33. (a) Neilsen, E. B.; Schellman, J. A. J. Phys. Chem. 1967, 71, 2297.
34. (b) Schellman, J. A.; Neilsen, E. B. J. Phys. Chem. 1967, 71, 3914.
35. (a) Kaya, K.; Nagakuru, S. J. Mol. Spectrosc. 1972, 44, 279.
36. (b) Kaya, K.; Nagakuru Theor. Chim. Acta 1967, 117.
37. Saidel, L. J. Arch. Biochem. Biophys. 1955, 56, 45.
38. Swenson, C. A.; Koob, L. J. J. Phys. Chem. 1970, 74, 3376.
39. Chen, X. G.; Lemmon, D. H.; Bormett, R. W.; Asher, S. A. Appl. Spectrosc. 1993, 47, 248.
40. (a) Asher, S. A. Anal. Chem. 1993, 65, 59A.
41. (b) Asher, S. A. Anal. Chem. 1993, 65, 201A.
42. (c) Asher, S. A.; Bormett, R. W.; Chen, X. G.; Lemmon, D. H.; Cho, N.; Peterson, P.; Arrigoni, M.; Spinelli, L.; Cannon, J. Appl. Spectrosc. 1993, 47, 628.
43. Holtz, J. S. W; Bormett, R. W.; Chi, Z.; Cho, N.; Chen, X. G.; Pajcini, V.; Asher, S. A.; Spinelli, L.; Owen, P.; Arrigoni, M. Appl. Spectrosc. In press.
44. Jones, C. M.; Devito, V. L.; Harmon, P. A.; Asher, S. A. Appl. Spectrosc. 1987, 41, 1268.
45. Dudik, J. M.; Johnson, C. R.; Asher, S. A. J. Chem. Phys. 1985, 82, 1732.
46. (a) DeVito, V. L.; Asher, S. A. J. Phys. Chem. Soc. 1992, 96, 6917.
47. (b) DeVito, V. L.; Asher, S. A. J. Am. Chem. Soc. 1989, 111, 9143.
48. Sutherland, J. C.; Keck, P. C.; Griffin, K. P.; Takacs, P. Z. Nucl. lnstrum. Methods 1982, 195, 375.
49. Albrecht, A. C.; Hutley, M. C. J. J. Chem. Phys. 1971, 55, 4438.
50. (a) Oboodi, M. R.; Alva, C.; Diem, M. J. Phys. Chem. 1984, 88, 501.
51. (b) Diem, M.; Lee, O.; Robert, G. M. J. Phys. Chem. 1992, 96, 548.
52. (c) Robert, G. M.; Lee, O.; Diem, M. J. Am. Chem. Soc. 1988, 110, 1749.
53. Wang, Y.; Purrello, R.; Georgiou, S.; Spiro, T. G. J. Am. Chem. Soc. 1991, 113, 6368.
54. Dudik, J. M.; Johnson, C. R.; Asher, S. A. J. Phys. Chem. 1985, 89, 3805.
55. (a) Long, D. A. Roman Spectroscopy; McGraw-Hill: New York, 1977.
56. (b) Udagawa, Y.; Iijima, M.; Ito, M. J. Raman Spectrosc. 1974, 2, 315.
57. Cantor, C. R.; Schimmel, P. R. Biophysical Chemistry, II, W. H. Freeman and Company, San Francisco, 1980; p 367.
58. The C-O bond lengths of the protonated carboxyl group of acetylglycine are 1.196 and 1.306 Å (Donohue, J.; Marsh, R. E. Acta Crystallogr. 1962, 15, 941). The C-O bond lengths of the deprotonated carboxylate group of alanylglycine are 1.263 and 1.260 Å (Koch, M. H. J.; Germain, G. Acta Crystallogr. Sect. B 1970, 26, 410). The average C-O bond length in the protonated carboxyl group contracts by 0.011 Å compared to that of the deprotonated carboxylate group.
59. The C-O bond lengths of the protonated carboxyl group of acetylglycine are 1.196 and 1.306 Å (Donohue, J.; Marsh, R. E. Acta Crystallogr. 1962, 15, 941). The C-O bond lengths of the deprotonated carboxylate group of alanylglycine are 1.263 and 1.260 Å (Koch, M. H. J.; Germain, G. Acta Crystallogr. Sect. B 1970, 26, 410). The average C-O bond length in the protonated carboxyl group contracts by 0.011 Å compared to that of the deprotonated carboxylate group.
60. Myers, A. B.; Mathies, R. A. Biological Applications of Raman Spectroscopy; Spiro, T. G., Ed.; John Wiley & Sons Inc.: New York, 1987; Vol. 2, p 1.
61. Li, P.; Sage, J. T.; Champion, P. M. J. Chem. Phys. 1992, 97, 3214.
62. (a)Shin, K-S. K.; Zink, J. I. J. Am. Chem. Soc. 1990, 112, 7148.
63. (b) Hildebrandt, P.; Tsuboi, M.; Spiro, T. G. J. Phys. Chem. 1990, 94, 2274.
64. Salem, L. The Molecular Orbital Theory of Conjugated Systems; W. A. Benjamin, Inc.: Reading, MA, 1966; p 65.