Structure of ortho-Substituted Arylboronic Acids - a Key to Sugar Receptor Activity
|Andrzej Sporzyński 1, Agnieszka Lewandowska 1, Beata T. Stepien 2, Michal K. Cyranski 2|
1. Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, Warszawa 00-664, Poland
Arylboronic acids are widely used as carbohydrate receptors [1, 2]. Their activity is based on the selective formation of esters with polyols. A typical fluorescent receptor consists of a fluorophore linked by a spacer to the receptor containing B(OH)2 group. Frequently used compounds are ortho-substituted boronic acids:
Intramolecular interactions play a key role in the mechanism of the fluorescence activity of such compounds. For the compounds with nitrogen atom in the beta position there is a possibility of intramolecular hydrogen bond formation (structure I) or N→B donor-acceptor interaction (structure II) [3, 4]:
The examples of the both types of the structures in solid state, as well as the spectroscopic characterization in solution will be discussed.
 T. D. James, S. Shinkai, Top. Curr. Chem. 2002, 218, 159.
 J. F. Callan, A. P. de Silva, D. C. Magri, Tetrahedron 2005, 61, 8551.
 L. Zhu, S. H. Shabbir, M. Gray, V. M. Lynch, S. Sorey, E. V. Anslyn, J. Am. Chem. Soc. 2006, 128, 1222.
 A. Sporzyński, A. Lewandowska, B. T. Stępień, M. K. Cyrański, to be published.
Presentation: oral at 18th Conference on Physical Organic Chemistry, Symposium 2, by Andrzej Sporzyński
See On-line Journal of 18th Conference on Physical Organic Chemistry
Submitted: 2006-06-20 14:02 Revised: 2009-06-07 00:44
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