Aggregation behavior of tetraenoic fatty acids in aqueous solution

Angewandte Chemie - International Edition

Volumn 46, Issue 8, 2007, Pages 1333-1336

  Wang, Yonghui ^a   Ma, Jianguo ^a   Cheon, Hwan Sung ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Aggregation; Chromophores; Doping; Fatty acids; Micelles

Indexed keywords

LIGHT ABSORPTION; MOLECULAR DYNAMICS; SOLUTIONS;

LOCAL SENSE; UV ABSORPTIONS;

FATTY ACIDS;

FATTY ACID; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SOLUTION AND SOLUBILITY; SPECTROSCOPY; TITRIMETRY;

FATTY ACIDS; MOLECULAR STRUCTURE; SOLUTIONS; SPECTRUM ANALYSIS; TITRIMETRY; WATER;

EID: 34247247627     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603979     Document Type: Article

References (32)

1. See Supporting Information for the syntheses of TE-FAs and TriE-FAs.
2. 18-t,t,t,t-TE-FAs I and II are known as α- and β-parinaric acids, respectively. Both I and II were isolated from the plant Parinarium glaberrimum [a) J. P. Riley, J. Chem. Soc. 1950, 12;
3. b) L. A. Sklar, B. S. Hudson, R. D. Simoni, Proc. Natl. Acad. Sci. USA 1975, 72, 1649]
4. and were used as a fluorescent probe for monitoring the complexation between methylated polysaccharides and fatty acids: c) K. K. Yabusaki, C. E. Ballou, Proc. Natl. Acad. Sci. USA 1978, 75, 691;
5. d) T. Kiho, C. E. Ballou, Biochemistry 1988, 27, 5824. (Chemical Equation Presented)
6. For the isolation and characterization of MMP, see: a) G. R. Gray, C. E. Ballou, J. Biol. Chem. 1971, 246, 6835;
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8. c) S. K. Maitra, C. E. Ballou, J. Biol. Chem. 1977, 252, 2459, and references therein.
9. The design and synthesis of sMMP and sMGP will be reported elsewhere, a) M. C. Hsu, J. Lee, Y. Kishi, unpublished results;
10. b) M. Meppen, Y. Wang, H.-S. Cheon, Y. Kishi, unpublished results.
11. For the isolation and characterization of MGLP/MGP, see: a) Y. C. Lee, C. E. Ballou, J. Biol. Chem. 1964, 239, PC3602;
12. b) L. S. Forsberg, A. Dell, D. J. Walton, C. E. Ballou, J. Biol. Chem. 1982, 257, 3555, and references therein. On the basis of the structure of the polysaccharide isolated from Mycobacterium bovis BCG, Rivière suggested a revision on the structure proposed by Ballou;
13. see: G. Tuffal, R. Albigot, M. Rivière, G. Puzo, Glycobiology 1998, 8, 675. Regarding the structural heterogeneity of MGP, Ballou commented that at least two forms of MGP containing 21 hexoses exist;
14. see: K. Kamisango, A. Dell, C. E. Ballou, J. Biol. Chem. 1987, 262, 4580;
15. see also: G. Tuffal, R. Albigot, B. Monsarrat, C. Ponthus, C. Picard, M. Rivière, G. Puzo, J. Carbohydr. Chem. 1995, 14, 631.
16. See Supporting Information for details.
17. UV spectroscopy studies showed that 1c forms a 1:1 complex with sMMP 16-mer and sMGP 16-mer: H.-S. Cheon, Y. Wang, J. Ma, Y. Kishi, ChemBioChem 2007, DOI: 10.1002/cbic.200600499.
18. a) R. M. Hochstrasser, M. Kasha, Photochem. Photobiol. 1964, 3, 317;
19. b) M. Kasha, H. R. Rawls, M. A. El-Bayoumi, Pure Appl. Chem. 1965, 11, 371;
20. c) for a review on this subject, see: P. W. Bohn, Annu. Rev. Phys. Chem. 1993, 44, 37.
21. a) D. G. Whitten, Acc. Chem. Res. 1993, 26, 502;
22. b) N. C. Maiti, S. Mazumdar, N. Periasamy, J. Phys. Chem. B 1998, 102, 1528.
23. For the aggregation of fatty acids containing an aromatic system, see: a) trans-stilbene: X. Song, C. Geiger, M. Farahat, J. Perlstein, D. G. Whitten, J. Am. Chem. Soc. 1997, 119, 12 481;
24. b) trans-azobenzene: X. Song, J. Perlstein, D. G. Whitten, J. Am. Chem. Soc. 1997, 119, 9144;
25. c) diphenylpolyene: S. P. Spooner, D. G. Whitten, J. Am. Chem. Soc. 1994, 116, 1240;
26. d) phenyl/biphenyl/terphenyl: H. C. Geiger, J. Perlstein, R. J. Lachicotte, K. Wyrozebski, D. G. Whitten, Langmuir 1999, 15, 5606.
27. 2+), and 3) the pH (pH 3.0, 7.0, and 10.0) significantly affect the formation and properties of the aggregates.
28. The aggregate formed from a 1:1 mixture of 3a and 3c did not give a characteristic blue-shifted UV peak, but rather gave a broad UV absorption. See Supporting Information for details.
29. On dilution with methanol, the sample with a broad UV absorption gave the normal UV absorption for tetraenes, thereby verifying that the broad UV absorption does not result from decomposition of the TE-FA.
30. 1-aggregate is irreversible. For details, see Figure 10 S in the Supporting Information.
31. 2-states were detected by UV spectroscopy. See Figure 7 S in the Supporting Information.
32. The aggregation behavior of chiral tetraenoic fatty acids will be reported elsewhere: J. Ma, H.-S. Cheon, Y. Kishi, Org. Lett. 2007, in press.