Structure of ortho-Substituted Arylboronic Acids - a Key to Sugar Receptor Activity

Andrzej Sporzyński 1Agnieszka Lewandowska 1Beata T. Stepien 2Michal K. Cyranski 2

1. Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, Warszawa 00-664, Poland
2. Warsaw University, Faculty of Chemistry, Pasteura 1, Warszawa 02-093, Poland

Abstract

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:

aspor1.jpg

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]:

aspor2.jpg

The examples of the both types of the structures in solid state, as well as the spectroscopic characterization in solution will be discussed.

[1] T. D. James, S. Shinkai, Top. Curr. Chem. 2002, 218, 159.

[2] J. F. Callan, A. P. de Silva, D. C. Magri, Tetrahedron 2005, 61, 8551.

[3] L. Zhu, S. H. Shabbir, M. Gray, V. M. Lynch, S. Sorey, E. V. Anslyn, J. Am. Chem. Soc. 2006, 128, 1222.

[4] A. Sporzyński, A. Lewandowska, B. T. Stępień, M. K. Cyrański, to be published.

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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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