A BINOL Based Fluorescence Sensor for Distinction of D-Glucose
Bangyu Xu
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Search for more papers by this authorJiting Hou
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Search for more papers by this authorCorresponding Author
Kun Li
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China, Tel.: 0086-028-85415886; Fax: 0086-028-85415886Search for more papers by this authorZhengwei Lu
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Search for more papers by this authorCorresponding Author
Xiaoqi Yu
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China, Tel.: 0086-028-85415886; Fax: 0086-028-85415886Search for more papers by this authorBangyu Xu
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Search for more papers by this authorJiting Hou
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Search for more papers by this authorCorresponding Author
Kun Li
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China, Tel.: 0086-028-85415886; Fax: 0086-028-85415886Search for more papers by this authorZhengwei Lu
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Search for more papers by this authorCorresponding Author
Xiaoqi Yu
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China
Key Laboratory of Green Chemistry and Technology (Ministry of Education), College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China, Tel.: 0086-028-85415886; Fax: 0086-028-85415886Search for more papers by this authorAbstract
A saccharide fluorescent receptor based on 1,1′-binaphthol was developed. The boronic acids groups are directly attached to the 3,3′-positions of BINOL which acted as probes to saccharides. The methyl protected receptor R1 showed better response to D-fructose compared to other saccharides in the fluorescence quenching experiment. To improve the selectivity of D-glucose, the triethylene glycol protected receptor R2 was developed. Receptor R2 has a better water-solubility than R1 that can be applied in completely aqueous environment. With receptor R2, D-glucose has a different response to other saccharides that can be useful for the distinction of D-glucose.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
cjoc_201400120_sm_suppl.pdf574.5 KB | suppl |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1
James, T. D.;
Phillips, M. D.;
Shinkai, S.,
Boronic Acids in Saccharide Recognition, RSC Publishing, Dorset, UK, 2006.
10.1039/9781847557612 Google Scholar
- 2 Wild, S.; Roglic, G.; Green, A.; Sicree, R.; King, H.. Diabetes Care, 2004, 27, 1047.
- 3 Smith, J. L. 2011. http://www.mendosa.com/noninvasive_glucose. pdf.
- 4 Peng, B.; Qin, Y.. Anal. Chem., 2008, 80, 6137.
- 5 Mazik, M.. Chem. Soc. Rev., 2009, 38, 935.
- 6 Xu, Z.; Yoon, J.; Spring, D. R.. Chem. Soc. Rev., 2010, 39, 1996.
- 7 Nishiyabu, R.; Kubo, Y.; James, T. D.; Fossey, J. S.. Chem. Commun., 2011, 47, 1124.
- 8 Feng, X.; Liu, L.; Wang, S.; Zhu, D.. Chem. Soc. Rev., 2010, 39, 2411.
- 9 Chen, X.; Pradhan, T.; Wang, F.; Kim, J. S.; Yoon, J.. Chem. Rev., 2012, 112, 1910.
- 10 Yang, Y.; Zhao, Q.; Feng, W.; Li, F.. Chem. Rev., 2013, 113, 192.
- 11 Zhang, Z.; Wang, H.; Zhang, H.; Liu, Y.. Chin. J. Chem., 2013, 31, 598.
- 12 Dai, H.; Xu, H.. Chin. J. Chem., 2012, 30, 267.
- 13 Yang, L.; Xu, K.; Wang, C.; Wang, C.. Chin. J. Org. Chem., 2013, 33, 2496 (in Chinese).
- 14 Guo, Z.; Shin, I.; Yoon, J.. Chem. Commun., 2012, 48, 5956.
- 15 James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S.. J. Chem. Soc., Chem. Commun., 1994, 477.
- 16 James, T. D.; Sandanayake, K.; Shinkai, S.. Angew. Chem., Int. Ed., 1996, 35, 1910.
- 17 Lorand, J. P.; Edwards, J. O.. J. Org. Chem., 1959, 24, 769.
- 18 Bull, S. D.; Davidson, M. G.; Elsen, J. M. H. V. d.; Fossey, J. S.; Jenkins, A. T. A.; Jiang, Y.-B.; Kubo, Y.; Marken, F.; Sakurai, K.; Zhao, J.; James, T. D.. Acc. Chem. Res., 2013, 46, 312.
- 19 Hansen, J. S.; Petersen, J. F.; Hoeg-Jensen, T.; Christensen, J. B.. Tetrahedron Lett., 2012, 53, 5852.
- 20 Noyori, R.. Acc. Chem. Res., 1990, 23, 345.
- 21 Chen, Y.; Yekta, S.; Yudin, A. K.. Chem. Rev., 2003, 103, 3155.
- 22 Pu, L.. Chem. Rev., 1998, 98, 2405.
- 23 Koc̆ovsky, P.; Vyskoc̆il, Š.; Smrc̆ina, M.. Chem. Rev., 2003, 103, 3213.
- 24 Ma, T.-H.; Dong, M.; Dong, Y.-M.; Wang, Y.-W.; Peng, Y.. Chem. Eur. J., 2010, 16, 10313.
- 25 Dong, M.; Peng, Y.; Dong, Y.-M.; Tang, N.; Wang, Y.-W.. Org. Lett., 2012, 14, 130.
- 26 Dong, Y.-M.; Peng, Y.; Dong, M.; Wang, Y.-W.. J. Org. Chem., 2011, 76, 6962.
- 27 Dong, M.; Wang, Y.-W.; Zhang, A.-J.; Peng, Y.. Chem. Asian J., 2013, 8, 1321.
- 28 Wang, Q.; Chen, X.; Tao, L.; Wang, L.; Xiao, D.; Yu, X.-Q.; Pu, L.. J. Org. Chem., 2007, 72, 97.
- 29 Lu, Q.-S.; Dong, L.; Zhang, J.; Li, J.; Jiang, L.; Huang, Y.; Qin, S.; Hu, C.-W.; Yu, X.-Q.. Org. Lett., 2009, 11, 669.
- 30 Chen, X.; Huang, Z.; Chen, S.-Y.; Li, K.; Yu, X.-Q.; Pu, L.. J. Am. Chem. Soc., 2010, 132, 7297.
- 31 Hou, J.-T.; Zhang, Q.-F.; Xu, B.-Y.; Lu, Q.-S.; Liu, Q.; Zhang, J.; Yu, X.-Q.. Tetrahedron Lett., 2011, 52, 4927.
- 32 Wang, M.-Q.; Li, K.; Hou, J.-T.; Wu, M.-Y.; Huang, Z.; Yu, X.-Q.. J. Org. Chem., 2012, 77, 8350.
- 33 Du, J.; Huang, Z.; Yu, X.-Q.; Pu, L.. Chem. Commun., 2013, 49, 5399.
- 34 Pu, L.. Acc. Chem. Res., 2012, 45, 150.
- 35 James, T. D.; Sandanayake, K.; Shinkai, S.. Nature, 1995, 374, 345.
- 36 Gray, C. W.; Houston, T. A.. J. Org. Chem., 2002, 67, 5426.
- 37 Zhao, J.; Fyles, T. M.; James, T. D.. Angew. Chem., Int. Ed., 2004, 43, 3461.
- 38 Ito, S.; Ono, K.; Iwasawa, N.. J. Am. Chem. Soc., 2012, 134, 13962.
- 39 Springsteen, G.; Wang, B. H.. Tetrahedron, 2002, 58, 5291.
- 40 Yoon, J.; Czarnik, A. W.. J. Am. Chem. Soc., 1992, 114, 5874.
- 41 Liu, Y.; Deng, C.; Tang, L.; Qin, A.; Hu, R.; Sun, J. Z.; Tang, B. Z.. J. Am. Chem. Soc., 2011, 660.
- 42 Bosch, L. I.; Fyles, T. M.; James, T. D.. Tetrahedron, 2004, 60, 11175.