The DOI matches its Crossref record; 6 of the 6 references it cites were found in a registry or an index.
An Improved Class of Sugar-Binding Boronic Acids, Soluble and Capable of Complexing Glycosides in Neutral Water
Abstract
This study describes a new class of carbohydrate-binding boronic acids. ortho-Hydroxymethyl phenylboronic acid (boronophthalide) was shown to be superior to the well-established dialkylamino ("Wulff-type") analogues, and it is more soluble in aqueous solvents. The most significant finding in this work is the surprising ability of ortho-hydroxyalkyl arylboronic acids to complex model glycopyranosides under physiologically relevant conditions. These boronic acid units appear to complex hexopyranosides mainly using their 4,6-diol. This behavior is significant because a majority of cell-surface glycoconjugates present free 4,6-diols. Thus, conjugatable forms of these boronic acids could be used in the design of oligomeric receptors and sensors to exploit multivalency effects. Such receptors could dramatically expand the potential of boronic acids toward the selective recognition of cell-surface glycoconjugates.
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Cites
A detailed examination of boronic acid–diol complexation
Springsteen, G., & Wang, B. (2002) · Tetrahedron · doi:10.1016/s0040-4020(02)00489-1 · Cited by 1,461
Saccharide Sensing with Molecular Receptors Based on Boronic Acid
James, T. D., Sandanayake, K. R. A. S., & Shinkai, S. (1996) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199619101 · Cited by 917
Teaching Old Indicators New Tricks
Wiskur, S. L., Ait-Haddou, H., Lavigne, J. J., & Anslyn, E. V. (2001) · Accounts of Chemical Research · doi:10.1021/ar9600796 · Cited by 763
Wang, W., Gao, X., & Wang, B. (2002) · Current Organic Chemistry · doi:10.2174/1385272023373446 · Cited by 257
ARENEBORONATES FROM DIOLS AND POLYOLS1
KUIVILA, H. G., KEOUGH, A. H., & SOBOCZENSKI, E. J. (1954) · The Journal of Organic Chemistry · doi:10.1021/jo01370a013 · Cited by 222
Non‐invasive glucose sensors and improved informatics – the future of diabetes management
Rohrscheib, M. R., Robinson, R., & Eaton, R. P. (2003) · Diabetes Obesity and Metabolism · doi:10.1046/j.1463-1326.2003.00275.x · Cited by 28
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Wei, Z., Yang, J. H., Zhou, J., Xu, F., Zrínyi, M., Dussault, P. H., Osada, Y., & Chen, Y. M. (2014) · Chem. Soc. Rev. · doi:10.1039/c4cs00219a · Cited by 896
Supramolecular Chemistry in Water
Oshovsky, G. V., Reinhoudt, D. N., & Verboom, W. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200602815 · Cited by 708
An Antifungal Agent Inhibits an Aminoacyl-tRNA Synthetase by Trapping tRNA in the Editing Site
Rock, F. L., Mao, W., Yaremchuk, A., Tukalo, M., Crépin, T., Zhou, H., Zhang, Y.-K., Hernandez, V., Akama, T., Baker, S. J., et al. (2007) · Science · doi:10.1126/science.1142189 · Cited by 631
Li, D., Chen, Y., & Liu, Z. (2015) · Chemical Society Reviews · doi:10.1039/c5cs00013k · Cited by 586
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Metadata
- Authors
- Dowlut, M., & Hall, D. G.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-03-15
- Volume
- 128
- Issue
- 13
- Pages
- 4226-4227
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2037667906
- Cited by
- 434
- References
- 6
- FWCI
- 9.97
- Type
- journal article
- Language
- en
- Open access
- closed
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