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A New Glucose-Selective Fluorescent Bisboronic Acid. First Report of Strong α-Furanose Complexation in Aqueous Solution at Physiological pH1
Abstract
A new bisboronic acid based glucose sensor 7 was synthesized from 9,10-bis(chloromethyl)anthracene and 2,2-dimethyl-1,3-propanediol protected 3-pyridineboronic acid. Due to its ionic structure 7 was found sufficiently water soluble for carbohydrate binding studies at neutral pH by means of NMR spectroscopy, fluorometry, and potentiometry. The p K a 's of 7 have been determined to 3.7 and 4.7 by potentiometric titration. From a solution of 7 and glucose (1:1) in water (pH 7.4) we observed the formation of a bisdentate boronic acid complex 7·Glu which has been assigned to a 1,2:3,5 bound α- d -glucofuranose complex. The evidence for this furanose structure comprises 1 H and 13 C NMR data with emphasis on the information from 1 J C - C coupling constants. Complex 7·Glu shows an increased fluorescence compared to 7 . The stability constant for the 1:1 complex (log K = 3.4) was determined from fluorometric titration, potentiometry, and NMR spectroscopy. Boronic acid 7 shows good selectivity for glucose compared to fructose and galactose.
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Cited by
Glucose Sensing in Supramolecular Chemistry
Sun, X., & James, T. D. (2015) · Chemical Reviews · doi:10.1021/cr500562m · Cited by 386
Zhang, L., Zhang, Z.-Y., Liang, R.-P., Li, Y.-H., & Qiu, J.-D. (2014) · Analytical Chemistry · doi:10.1021/ac500289c · Cited by 382
Kong, K. V., Lam, Z., Lau, W. K. O., Leong, W. K., & Olivo, M. (2013) · Journal of the American Chemical Society · doi:10.1021/ja409230g · Cited by 173
Fluorescence Glucose Detection: Advances Toward the Ideal In Vivo Biosensor
Moschou, E. A., Sharma, B. V., Deo, S. K., & Daunert, S. (2004) · Journal of Fluorescence · doi:10.1023/b:jofl.0000039341.64999.83 · Cited by 154
Kong, K. V., Ho, C. J. H., Gong, T., Lau, W. K. O., & Olivo, M. (2014) · Biosensors and Bioelectronics · doi:10.1016/j.bios.2013.12.062 · Cited by 81
Metadata
- Authors
- Eggert, H., Frederiksen, J., Morin, C., & Norrild, J. C.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-05-01
- Volume
- 64
- Issue
- 11
- Pages
- 3846-3852
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2949105946
- Cited by
- 260
- References
- 0
- FWCI
- 9.17
- Type
- journal article
- Language
- en
- Open access
- closed
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- Eggert, H., Frederiksen, J., Morin, C., & Norrild, J. C. (1999). A New Glucose-Selective Fluorescent Bisboronic Acid. First Report of Strong α-Furanose Complexation in Aqueous Solution at Physiological pH1. The Journal of Organic Chemistry. https://doi.org/10.1021/jo9819279
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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