1H NMR spectroscopic investigations on the conformation of amphiphilic aromatic amino acid derivatives in solution: Effect of chemical architecture of amphiphiles and polarity of solvent medium

Journal of Physical Chemistry B

Volumn 114, Issue 43, 2010, Pages 13691-13702

  Vijay, R ^a   Mandal, A B ^b   Baskar, Geetha ^a  

^a Industrial Chemistry Laboratory   (India)

^b CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; AMINO ACIDS; AROMATIC COMPOUNDS; DIMETHYL SULFOXIDE; ESTERS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS;

ALIPHATIC CHAINS; ALKYL CHAIN; AMPHIPHILICS; AROMATIC AMINO ACID; AROMATIC RINGS; CHEMICAL STRUCTURE; EFFECT OF CHEMICALS; H NMR SPECTRA; L-PHENYLALANINE; L-TYROSINE; MOLECULAR MODELS; NUCLEAR OVERHAUSER ENHANCEMENT; PHENYL RINGS; SHIFT-AND; SOLVENT POLARITY; SPECTROSCOPIC INVESTIGATIONS;

CONFORMATIONS;

DEUTERIUM OXIDE; DIMETHYL SULFOXIDE; DRUG DERIVATIVE; ESTER; PHENYLALANINE; SOLVENT; TYROSINE;

ARTICLE; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTION AND SOLUBILITY;

DEUTERIUM OXIDE; DIMETHYL SULFOXIDE; ESTERS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHENYLALANINE; SOLUTIONS; SOLVENTS; TYROSINE;

EID: 78549287112     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp104194j     Document Type: Article

References (67)

1. Liu, Q. F.; Wei, W.; Lu, M.; Sun, F.; Li, J.; Zhang, Y. C. Catal. Lett. 2009, 131, 485.
2. Branco, L. C.; Ferreira, F. C.; Santos, J. L.; Crespo, J. G.; Afonso, C. A. M. Adv. Synth. Catal. 2008, 350, 2086.
3. Itoh, J.; Fuchibe, K.; Akiyama, T. Synthesis 2006, 4075.
4. Ikkala, O.; ten Brinke, G. Science 2002, 295, 2407.
5. Zhang, D. B.; Qi, L. M.; Ma, J. M.; Cheng, H. M. Adv. Mater. 2002, 14, 1499.
6. Jiang, C. L.; Wang, Y. F. Mater. Chem. Phys. 2009, 113, 531.
7. Cheng, Y. Y.; Wu, Q. L.; Li, Y. W.; Hu, J. J.; Xu, T. W. J. Phys. Chem. B 2009, 113, 8339.
8. Torchilin, V. P. J. Controlled Release 2001, 73, 137.
9. Uchegbu, I. F.; Vyas, S. P. Int. J. Pharm. 1998, 172, 33.
10. Lawrence, M. J. Chem. Soc. Rev. 1994, 23, 417.
11. Miller, D. J.; Henning, T.; Grunbein, W. Colloids Surf., A 2001, 183, 681.
12. Nishimoto, M.; Morimitsu, T.; Tamai, N.; Kaneshina, S.; Nagamune, H.; Matsuki, H. Colloids Surf., B 2010, 75, 80.
13. Anderson, J. M.; Andukuri, A.; Lim, D. J.; Jun, H.-W. ACS Nano 2009, 3, 3447.
14. Fernandez, G.; Garcia, F.; Aparicio, F.; Matesanz, E.; Sanchez, L. Chem. Commun. (Cambridge, U. K.) 2009, 7155.
15. Zhou, W.; Gu, W.; Xu, Y.; Pecinovsky, C. S.; Gin, D. L. Langmuir 2003, 19, 6346.
16. Rizvi, S. A. A.; Shamsi, S. A. Electrophoresis 2003, 24, 2514.
17. Zhang, Y. J.; Jin, M.; Lu, R.; Song, Y. L.; Jiang, L.; Zhao, Y. Y.; Li, T. J. J. Phys. Chem. B 2002, 106, 1960.
18. Infante, M. R.; Perez, L.; Pinazo, A.; Clapes, P.; Moran, M. C.; Angelet, M.; Garcia, M. T.; Vinardell, M. P. C. R. Chim. 2004, 7, 583.
19. Tuin, G.; Candau, F.; Zana, R. Colloids Surf., A 1998, 131, 303.
20. Matsuoka, K.; Yonekawa, A.; Ishii, M.; Honda, C.; Endo, K.; Moroi, Y.; Abe, Y.; Tamura, T. Colloid Polym. Sci. 2006, 285, 323.
21. Ryhanen, S. J.; Sally, V. M. J.; Parry, M. J.; Luciani, P.; Mancini, G.; Alakoskela, J. M. I.; Kinnunen, P. K. J. J. Am. Chem. Soc. 2006, 128, 8659.
22. Bakshi, M. S.; Kaur, N.; Mahajan, R. K.; Singh, J.; Singh, N. Colloid Polym. Sci. 2006, 284, 879.
23. Gaspar, L. J. M.; Baskar, G.; Reddy, B. S. R. Langmuir 2004, 20, 9029.
24. Gaspar, L. J. M.; Baskar, G. Biomacromolecules 2006, 7, 1318.
25. Lakowicz; J. R. Principles of Fluorescence Spectroscopy; Academic/Plenum Publishers: New York.
26. Vijay, R.; Angayarkanny, S.; Baskar, G. Colloids Surf., A 2008, 317, 643.
27. Marx, K. A.; Alva, K. S.; Sarma, R. Mater. Sci. Eng., C 2000, 11, 155.
28. Marx, K. A.; Lee, J. S.; Sung, C. Biomacromolecules 2004, 5, 1869.
29. Fukuda, K.; Shibasaki, Y.; Nakahara, H.; Liu, M. h. Adv. Colloid Interface Sci. 2000, 87, 113.
30. Chhatre, A. S.; Joshi, R. A.; Kulkarni, B. D. J. Colloid Interface Sci. 1993, 158, 183.
31. Holmberg, K. Curr. Opin. Colloid Interface Sci. 2003, 8, 187.
32. Merritt, M. V.; Chang, I. W.; Flannery, C. A.; Hsieh, S.-J.; Lee, K.; Yung, J. J. Am. Chem. Soc. 1995, 117, 9791.
33. Vijay, R.; Singh, J.; Baskar, G.; Ranganathan, R. J. Phys. Chem. B 2009, 113, 13959.
34. Melvin, A.; Vijay, R.; Chaudhari, V. R.; Gupta, B.; Prakash, R.; Haram, S.; Baskar, G.; Khushalani, D. J. Colloid Interface Sci. 2010, 346, 265.
35. Loksztejn, A.; Dzwolak, W. Biochemistry 2009, 48, 4846.
36. Yang, Z. R. W.; Tendian, S. W.; Carson, W. M.; Brouillette, W. J.; Delucas, L. J.; Brouillette, C. G. Protein Sci. 2004, 13, 830.
37. Markarian, S. A.; Terzyan, A. M. J. Chem. Eng. Data 2007, 52, 1704.
38. Rodriguez, A.; del Mar Graciani, M.; Angulo, M.; Moya, M. L. Langmuir 2007, 23, 11496.
39. Sorensen-Stowell, K.; Hengge, A. C. J. Org. Chem. 2006, 71, 7180.
40. Bernasconi, C. F.; Fairchild, D. E.; Montanez, R. L.; Aleshi, P.; Zheng, H. B.; Lorance, E. J. Org. Chem. 2005, 70, 7721.
41. Llauger, L.; Miranda, M. A.; Cosa, G.; Scaiano, J. C. J. Org. Chem. 2004, 69, 7066.
42. Catalan, J.; Diaz, C.; Garcia-Blanco, F. J. Org. Chem. 2001, 66, 5846.
43. Bernasconi, C. F.; Leyes, A. E.; Rappoport, Z. J. Org. Chem. 1999, 64, 2897.
44. Ariga, K.; Anslyn, E. V. J. Org. Chem. 1992, 57, 417.
45. Das, S.; Bhirud, R. G.; Nayyar, N.; Narayan, K. S.; Kumar, V. V. J. Phys. Chem. 1992, 96, 7454.
46. Yuan, H. Z.; Tan, X. L.; Cheng, G. Z.; Zhao, S.; Zhang, L.; Mao, S. Z.; An, J. Y.; Yu, J. Y.; Du, Y. R. J. Phys. Chem. B 2003, 107, 3644.
47. Baskar, G.; Baran Mandal, A. Chem. Phys. Lett. 1997, 266, 443.
48. Baskar, G.; Mandal, A. B. Langmuir 2000, 16, 3957.
49. Yuan, H.-Z.; Cheng, G.-Z.; Zhao, S.; Miao, X.-J.; Yu, J.-Y.; Shen, L.-F.; Du, Y.-R. Langmuir 2000, 16, 3030.
50. Yuan, H. Z.; Zhao, S.; Cheng, G. Z.; Zhang, L.; Miao, X. J.; Mao, S. Z.; Yu, J. Y.; Shen, L. F.; Du, Y. R. J. Phys. Chem. B 2001, 105, 4611.
51. Kim, B.-J.; Im, S.-S.; Oh, S.-G. Langmuir 2000, 17, 565.
52. Kabir ud, D.; Fatma, W.; Khan, Z. A.; Dar, A. A. J. Phys. Chem. B 2007, 111, 8860.
53. Furo, I. J. Mol. Liq. 2005, 117, 117.
54. Ma, J.-h.; Guo, C.; Tang, Y.-l.; Liu, H.-z. Langmuir 2007, 23, 9596.
55. Bernardez, L. A. Colloids Surf., A 2008, 324, 71.
56. Yang, Q. Q.; Zhou, Q.; Somasundaran, R. J. Mol. Liq. 2009, 146, 105.
57. Zhang, S. Z.; Fu, X. J.; Wang, H.; Yang, Y. J. Chin. Chem. Lett. 2008, 19, 1119.
58. Andrade-Dias, C.; Lima, S.; Teixeira-Dias, J. J. J. Colloid Interface Sci. 2007, 316, 31.
59. Ernst, R. R.; Bodenhausen, G.; Wokaun, A. Principles of Nuclear Magnetic Resonance in One and Two Dimensions; Oxford University Press: New York, 1987.
60. Macura, S.; Ernst, R. R. Mol. Phys. 1980, 41, 95.
61. Kriz, J.; Dybal, J. i. J. Phys. Chem. B 2010, 114, 3140.
62. Suzuki, M.; Sano, M.; Kimura, M.; Hanabusa, K.; Shirai, H. Eur. Polym. J. 1999, 35, 1079.
63. Luan, Y. X.; Song, A. X.; Xu, G. Y. Soft Matter 2009, 5, 2587.
64. Yang, L. J.; Yang, X. Q.; Huang, K. M.; Jia, G. Z.; Shang, H. Int. J. Mol. Sci. 2009, 10, 1261.
65. Rule, G. S.; Hitchens, T. K. Focus on Structural Biology, 26th ed.; Springer: Dordrecht; Vol. 5, 2006.
66. Yuan, H. Z.; Tan, X. L.; Cheng, G. Z.; Zhao, S.; Zhang, L.; Mao, S. Z.; An, J. Y.; Yu, J. Y.; Du, Y. R. J. Phys. Chem. B 2003, 107, 3644.
67. Borgias, B. A.; Gochin, M.; Kerwood, D. J.; James, T. L. Prog. Nucl. Magn. Reson. Spectrosc. 1990, 22, 83.