Biotin-amino acid conjugates: An approach toward self-assembled hydrogelation

Organic Letters

Volumn 7, Issue 9, 2005, Pages 1741-1744

  Bhuniya, Sankarprasad ^a   Sun, Min Park ^a   Byeang, Hyean Kim ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AMINO ACID DERIVATIVE; BIOTIN; BUFFER;

ARTICLE; CONJUGATION; GELATION; MOLECULAR WEIGHT; PH;

AMINO ACIDS; BIOTIN; DRUG CARRIERS; HYDROGELS; HYDROGEN-ION CONCENTRATION; MICROSCOPY, ELECTRON, SCANNING; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; ZIDOVUDINE;

EID: 18844461191     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050300r     Document Type: Article

References (36)

1. Okano, T. Biorelated Polymers and Gels; Academic Press: San Diego, 1998.
2. Dagani, R. Chem. Eng. News 1997, 75, 26.
3. (a) Nishikawa, T.; Akiyoshi, K.; Sunamoto, J. J. Am. Chem. Soc. 1996, 118, 6110.
4. (b) Osada, Y.; Gong, J. P. Adv. Mater. 1998, 10, 827.
5. (a) Oda, R.; Huc, I.; Candau, S. J. Angew. Chem., Int. Ed. 1998, 37, 2689.
6. (b) Oda, R.; Huc, I.; Schmutz, M.; Chandu, S. J.; MacKintosh, F. C. Nature 1999, 399, 566.
7. (c) Menger, F. M.; Caram, K. L.; Seredyuk, V. A.; Apkarian, R. P. J. Am. Chem. Soc. 2002, 124, 1140.
8. (a) Tachibana, T.; Kamabara, H. J. Am. Chem. Soc. 1965, 87, 3015.
9. (b) Yanagawa, H.; Ogawa, Y. Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567.
10. (c) Bhattacharya, S.; Acharya, S. N. G. Chem. Mater. 1999, 11, 3504.
11. (a) Shimizu, T.; Masuda, M. J. Am. Chem. Soc. 1997, 119, 2812.
12. (b) Iwaura, R.; Yoshida, K.; Masuda, U.; Yase, K.; Shimizu, T. Chem. Mater. 2002, 14, 3047.
13. (c) Iwaura, R.; Yoshida, K.; Masuda, M.; Ohnishi-Kameyama, M.; Yoshida, M.; Shimizu, T. Angew. Chem., Int. Ed. 2003, 42, 1009.
14. (a) Hamilton, A. D.; Estroff, L. A. Angew. Chem., Int. Ed. 2000, 39, 3447.
15. (b) Maitra, U.; Mukhopadhyay, S.; Sarkar, A.; Rao, P.; Indi, S. Angew. Chem., Int. Ed. 2001, 40, 2281.
16. (c) Hirst, A. R.; Smith, D. K.; Feiters, M. C.; Geurts, H. P. M.; Wright, A. C. J. Am. Chem. Soc. 2003, 125, 9010.
17. (d) Park, S. M.; Lee, Y. S.; Kim, B. H. Chem. Commun. 2003, 2912.
18. (e) Köhler, K.; Förster, G.; Hauser, A.; Dobner, B.; Heiser, U. F.; Ziethe, F.; Richter, W.; Steniger, F.; Drechsler, M.; Stettin, H.; Blume, A. Angew. Chem., Int. Ed. 2004, 43, 245.
19. (f) Yang, Z.; Gu, H. W.; Zhang, Y.; Wang, L.; Xu, B. Chem. Commun. 2004, 208.
20. (g) Numata, K. M.; Fujita, N.; Park, S. M., Yun, Y. J.; Kim, B. H.; Shinkai, S. Chem. Commun. 2004, 1996.
21. Xing, B.; Yu, C.-W.; Chow, K.-H.; Ho, P.-L.; Fu, D.; Xu, B. J. Am. Chem. Soc. 2002, 124, 14846.
22. Crisp, G. T.; Gore, J. Synth. Commun. 1997, 27, 2203.
23. Friedrich, W. Vitamins; Walter de Grueter & Co.: Berlin, 1998; see also references therein.
24. (a) Hofmann, K.; Titus, G.; Montibeller, J. A. Finn, F. A. Biochemistry 1982, 21, 978.
25. (b) Weber, P. C.; Ohlendorf, D. H.; Wendoloski, J. J.; Salemme, F. R. Science 1989, 24, 85.
26. Menger, F. M.; Caran, K. L. J. Am. Chem. Soc. 2000, 122, 11679.
27. Xerogel of hydrogelators was obtained by freezing and pumping the gels of correspoding gelators for 6 h.
28. See Supporting Information.
29. 1H NMR data.
30. (a) Suzuki, M.; Yumoto, M.; Kimura, M.; Shirai, M.; Hanabusa, K. Helv. Chim. Acta 2003, 86, 2228.
31. (b) Kogigo, M.; Yumoto, M.; Kimura, M.; Shirai, H.; Hanabusa, K. Chem. Eur. J. 2003, 9, 348.
32. (a) Billiot, F. H.; McCarroll, M.; Billiot, E. J.; Rugutt, J. K.; Morris, K.; Warner, I. M. Langmuir 2002, 18, 2993.
33. (b) Rabenstein, D. L. J. Am. Chem. Soc. 1973, 95, 2797.
34. DeTitta, G. T.; Eddmonds, J. W.; Stallings, W.; Donohue, J. J. Am. Chem. Soc. 1976, 98, 1920.
35. We used MOPAC6 software (available at http://www.ccl.net) to estimate the hydrogen bonding interactions among these molecules.
36. We did not extend this experiment further by addition of higher concentration of streptadividin, as its solubility in water is very low (0.1 mg/mL).