Supramolecular structures from lysine peptides and carbon dioxide

Journal of Organic Chemistry

Volumn 71, Issue 23, 2006, Pages 8696-8705

  Stastny, Vaclav ^a   Anderson, Anjenique ^a   Rudkevich, Dmitry M ^a  

^a UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; BENZENE; CARBON DIOXIDE; GELS; ORGANIC SOLVENTS; SUPRAMOLECULAR CHEMISTRY; TEMPERATURE CONTROL;

CO2; COUMARIN; LYSINE PEPTIDES; NOVEL LINEAR POLYMERS;

ORGANIC POLYMERS;

BENZENE; CARBAMIC ACID DERIVATIVE; CARBON DIOXIDE; COUMARIN; LYSINE; METHANOL; MONOMER; ORGANIC SOLVENT; TRICHLOROETHYLENE; TRIPEPTIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CROSS LINKING; ENVIRONMENTAL TEMPERATURE; PHYSICAL PARAMETERS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

CARBON DIOXIDE; COUMARINS; HYDROGEN BONDING; LYSINE; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PEPTIDES; POLYMERS; SENSITIVITY AND SPECIFICITY;

EID: 33750874753     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061144k     Document Type: Article

References (41)

1. (a) Supmmolecular Polymers, 2nd ed.; Ciferri, A., Ed.; CRC Press: Boca Raton, FL, 2005.
2. (b) Bosman, A. W.; Brunsveld, L.; Folmer, B. J. B.; Sijbesma, R. P.; Meijer, E. W. Macromol. Symp. 2003, 201, 143-154.
3. (c) Lehn, J.-M. Polym. Int. 2002, 51, 825-839.
4. (d) Schubert, U. S.; Eschbaumer, C. Angew. Chem., Int. Ed. 2002, 41, 2892-2926.
5. (e) ten Cate, A. T.; Sijbesma, R. P. Macromol. Rapid Commun. 2002, 23, 1094-1112.
6. (f) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097.
7. (g) Schmuck, C.; Wienand, W. Angew. Chem., Int. Ed. 2001, 40, 4363-4369.
8. (h) Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci. USA 1997, 94, 7132-7137.
9. (i) Lange, R. F. M.; van Gurp, M.; Meijer, E. W. J. Polym. Sci., Part A 1999, 37, 3657-3670.
10. (j) Castellano, R. K.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3657-3663.
11. Review from this laboratory: Rudkevich, D. M.; Xu, H. Chem. Commun. 2005, 2651-2659.
12. (a) Zhao, X.; Zhang, S. Trends Biotechnol. 2004, 22, 470-476.
13. (b) Voyer, N.; Lamothe, J. Tetrahedron 1995, 51, 9241-9284.
14. (a) Dell'Amico, D. B.; Calderazzo, F.; Labella, L.; Marchetti, F.; Pampaloni, G. Chem. Rev. 2003, 103, 3857-3898.
15. (b) Hampe, E. M.; Rudkevich, D. M. Tetrahedron 2003, 59, 9619-9625.
16. (c) Masuda, K.; Ito, Y.; Horiguchi, M.; Fujita, H. Tetrahedron 2005, 61, 213-229.
17. (a) Yamaguchi, T.; Koval, C. A.; Nobel, R. D.; Bowman, C. Chem. Eng. Sci. 1996, 51, 4781-4789.
18. (b) Yamaguchi, T.; Boetje, L. M.; Koval, C. A.; Noble, R. D.; Bowman, C. N. Ind. Eng. Chem. Res. 1995, 34, 4071-4077.
19. (c) Kosaraju, P.; Kovvali, A. S.; Korikov, A.; Sirkar, K. K. Ind. Eng. Chem. Res. 2005, 44, 1250-1258 and references therein.
20. (d) Bates, E. D.; Mayton, R. D.; Ntai, I.; Davis, J. H., Jr. J. Am. Chem. Soc. 2002, 124, 926-927.
21. (a) George, M.; Weiss, R. G. J. Am. Chem. Soc. 2001, 123, 10393-10394.
22. (b) George, M.; Weiss, R. G. Langmuir 2002, 18, 7124-7135.
23. (c) George, M.; Weiss, R. G. Langmuir 2003, 19, 1017-1025.
24. (d) George, M.; Weiss, R. G. Langmuir 2003, 19, 8168-8176.
25. (e) Carretti, E.; Dei, L.; Baglioni, P.; Weiss, R. G. J. Am. Chem. Soc. 2003, 125, 5121-5129.
26. (a) Davis, A. S.; O'Brien, P.; Nunn, P. B. Bioorg. Chem. 1993, 21, 309-318.
27. (b) Chen, J.-G.; Sandberg, M.; Weber, S. G. J. Am. Chem. Soc. 1993, 115, 7343-7350.
28. (c) McGhee, W.; Riley, D.; Christ, K.; Pan, Y.; Parnas, B. J. Org. Chem. 1995, 60, 2820-2830.
29. For the preliminary results from this laboratory, see: (a) Xu, H.; Rudkevich, D. M. Chem.-Eur. J. 2004, 10, 5432-5442.
30. (b) Rudkevich, D. M.; Woldemariam, G. A.; Xu, H. Polym. Prepr. 2005, 6, 1162-1163.
31. MacroModel 7.1; MM2 and Amber* Force Field. See: Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
32. (a) Hampe, E. M.; Rudkevich, D. M. Chem. Commun. 2002, 1450-1451.
33. (b) Aresta, M.; Ballivet-Tkatchenko, D.; Dell'Amico, D. B.; Bonnet, M. C.; Boschi, D.; Calderazzo, F.; Faure, R.; Labella, L.; Marchetti, F. Chem. Commun. 2000, 1099-1100 and references therein.
34. (c) Wittmann, K.; Wisniewski, W.; Mynott, R.; Leitner, W.; Kranemann, C. L.; Rische, T.; Eilbracht, P.; Kluwer, S.; Ernsting, J. M.; Elsevier, C. J. Chem.-Eur. J. 2001, 7, 4584-4589.
35. (d) Fürstner, A.; Ackermann, L.; Beck, K.; Hori, H.; Koch, D.; Langemann, K.; Liebl, M.; Six, C.; Leitner, W. J. Am. Chem. Soc. 2001, 123, 9000-9006.
36. 3) solutions. For the discussion, see: Ito, Y.; Ushitora, H. Tetrahedron 2006, 62, 226-235.
37. 2 in DMSO solution. For the detailed discussion, see ref 4c.
38. For the preliminary results from this laboratory, see: Xu, H.; Rudkevich, D. M. Org. Lett. 2005, 7, 3223-3226.
39. max = 358 nm was recorded. No visible changes were observed after 10 min.
40. Xiaoding, X.; Moulijn, J. A. Energy Fuels 1996, 10, 305-325.
41. Xu, H.; Kinsel, G. R.; Zhang, J.; Li, M.; Rudkevich, D. M. Tetrahedron 2003, 59, 5837-5848.