Directed molecular recognition: Design and synthesis of neutral receptors for biotin to bind both its functional groups

Journal of Organic Chemistry

Volumn 71, Issue 19, 2006, Pages 7280-7287

  Goswami, Shyamaprosad ^a   Dey, Swapan ^a  

^a INDIAN INSTITUTE OF ENGINEERING SCIENCE AND TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULES; ORGANIC COMPOUNDS; PROTEINS; SYNTHESIS (CHEMICAL); UREA; VITAMINS;

BIOTIN; CHLOROFORM; MOLECULAR RECOGNITION; NEUTRAL RECEPTORS;

MOLECULAR DYNAMICS;

BIOTIN; CARBOXYL GROUP; CHLOROFORM; FUNCTIONAL GROUP; UREA;

ARTICLE; COMPLEX FORMATION; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

BINDING SITES; BIOTIN; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIDINES;

EID: 33748999268     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061013j     Document Type: Article

References (35)

1. Lehn, J. M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, Germany, 1995.
2. (b) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383.
3. (a) Mazik, M.; Radunz, W.; Boese, R. J. Org. Chem. 2004, 69, 7448.
4. (b) Chou, H.-C.; Hsu, C.-H.; Cheng, Y.-M.; Cheng, C.-C.; Liu, H.-W.; Pu, S.-C.; Chou, P.-T. J. Am. Chem. Soc. 2004, 126, 1650.
5. (c) Hegde, V.; Hung, C.-Y.; Madhukar, P.; Cunningham, R.; Hopfner, T.; Thummel, R. P. J. Am. Chem. Soc. 1993, 115, 872.
6. (d) Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210.
7. (a) Goswami, S. P.; Ghosh, K.; Dasgupta, S. J. Org. Chem. 2000, 65, 1907.
8. (b) Goswami, S. P.; Ghosh, K.; Mukherjee, R. Tetrahedron 2001, 57, 4987.
9. (c) Goswami, S. P.; Ghosh, K.; Mukherjee, R. J. Ind. Chem. Soc. 1999, 661.
10. (d) Goswami, S. P.; Ghosh, K.; Dasgupta, S. Tetrahedron 1996, 52, 12223.
11. (e) Alvarez-Rua, C.; Garci̊a-Granda, S.; Goswami, S. P.; Mukherjee, R.; Dey, S.; Claramunt, R. M.; Santa Maria, M. D.; Rozas, I.; Jagerovic, N.; Alkorta, I.; Elguero, J. New J. Chem. 2004, 28, 700.
12. Goswami, S. P.; Dey, S.; Maity, A. C.; Jana, S. Tetrahedron Lett. 2005, 46, 1315.
13. (a) Goswami, S. P.; Hamilton, A. D.; Van Engen, D. J. Am. Chem. Soc. 1989, 111, 3425.
14. (b) Goswami, S. P.; Mahapatra, A. K.; Mukherjee, R. J. Chem. Soc., Perkin Trans. 1 2001, 2717.
15. (c) Goswami, S. P.; Mukherjee, R. Tetrahedron Lett. 1997, 38, 1619.
16. (d) Goswami, S. P.; Mukherjee, R.; Roy, J. Org. Lett. 2005, 7, 1283.
17. Nelson, D. L.; Cox, M. M. Lehninger Principles of Biochemistry, 3rd ed.; Worth Publishers: New York, 2000.
18. Confalone, P. N.; Pizzolato, G.; Lollar-Confalone, D.; Uskokovic, M. R. J. Am. Chem. Soc. 1980, 102, 1954.
19. (a) DeTitta, G. T.; Edmonds, J. W.; Stallings, W.; Donohue, J. J. Am. Chem. Soc. 1976, 98, 1920.
20. (b) DeTitta, G. T.; Blessing, R. H.; Moss, G. R.; King, H. F.; Sukumaran, D. K.; Roskwitalski, R. L. J. Am. Chem. Soc. 1994, 116, 6485.
21. (a) Adrian, J. C., Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1989, 111, 8055.
22. (b) Rao, P.; Maitra, U. Supramol. Chem. 1998, 9, 325.
23. (a) Herranz, F.; Santa Marý'a, M. D.; Claramunt, M. R. J. Org. Chem. 2006, 71, 2944.
24. (b) Rosa, M.; Claramunt, R. M.; Herranz, F.; Marý'a, M. D. S.; Pinilla, E.; Torres, M. R.; Elguero, J. Tetrahedron 2005, 61, 5089.
25. (c) Rosa, M.; Claramunt, R. M.; Herranz, F.; Marý'a, M. D. S.; Jaime, C.; Federicob, M. D.; Elguero, J. Biosens. Bioelectron. 2004, 20, 1242.
26. (d) Peikert, C.; Seeger, K.; Bhat, R. K.; Berger, S. Org. Biomol. Chem, 2004, 2, 1777.
27. Papadopoulon, M. V.; Goswami, S. P.; Hamilton, A. D. J. Heterocyclic Chem. 1995, 32, 2675.
28. See the Supporting Information.
29. PCMODEL Serena Software 93.
30. a proton of receptor 3 as a function of molar concentration of biotin.
31. a) calculations see: (a) Connors, K. A. Binding Constants; The Measurement of Molecular Complex Stability; Wiley-Interscience: New York, 1987.
32. (b) Liao, J.-H.; Chen, C.-T.; Chou, H.-C.; Cheng, C.-C.; Chou, P.-T.; Fang, J.-M.; Slanina, Z.; Chow, T. J. Org. Lett. 2002, 4, 3107.
33. (a) By Foster-Fyfe analysis of the titration data at 25 °C. Foster, F.; Fyfe, C. A. Prog. Nucl. Magn. Reson. Spectrosc. 1969, 4, 1.
34. (b) Fielding, L. Tetrahedron 2000, 56, 6151.
35. Mazik, M.; Blaser, D.; Boese, R. Tetrahedron 1999, 55, 12771.