"Click-fluors": Modular fluorescent saccharide sensors based on a 1,2,3-triazole ring

Journal of Organic Chemistry

Volumn 73, Issue 7, 2008, Pages 2871-2874

  Scrafton, David K ^a   Taylor, James E ^a   Mahon, Mary F ^a   Fossey, John S ^a   James, Tony D ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CARBOHYDRATES; FLUORESCENCE; SACCHARIFICATION;

FLUORESCENT SENSOR ARRAYS; MODULAR FLUORESCENT SACCHARIDE SENSORS;

CHEMICAL SENSORS;

ACETYLENE; BORONIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; FRUCTOSE; GALACTOSE; MANNOSE; TRIAZOLE; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; CYCLOADDITION; FLUORESCENCE; METABOLISM; MOLECULAR STABILITY; SCREENING; SENSOR; TITRIMETRY;

BORONIC ACIDS; CARBOHYDRATES; CRYSTALLOGRAPHY, X-RAY; FLUORESCENT DYES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; TRIAZOLES;

EID: 41649091459     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702584u     Document Type: Article

References (22)

1. Garrett, R. H.; Grisham, C. M. Biochemistry, 2nd ed.; Saunders College Publishing; Wiley-VCH: London, 1999.
2. Davis, A. P.; James, T. D. In Functional Synthetic Receptors; Schrader, T., Hamilton, A. D., Eds.; Wiley-VCH: Weinheim, 2005; pp 45-110.
3. Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. 1999, 38, 2978-2996.
4. Hall, D. G., Ed. Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine; 2005.
5. James, T. D.; Phillips, M. D.; Shinkai, S. Boronic Acids in Saccharide Recognition; RSC Publishing: Cambridge, UK, 2006.
6. James, T. D.; Shinkai, S. Top. Curr. Chem. 2002, 218, 159-200.
7. (a) Arimori, S.; Bosch, L. I.; Ward, C. J.; James, T. D. Tetrahedron Lett. 2001, 42, 4553-4555.
8. (b) Bosch, L. I.; Mahon, M. F.; James, T. D. Tetrahedron Lett. 2004, 45, 2859-2862.
9. (c) Bosch, L. I.; James, T. D. In Topics in Fluorescence Spectroscopy; Geddes, C. D., Lakowicz, J. R., Eds.; Springer: New York, 2006; Vol. 11, pp 344-350.
10. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984.
11. Zhu, L.; Anslyn, E. V. Angew. Chem., Int. Ed. 2006, 45, 1190-1196.
12. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
13. We have used the phrase "click-fluor" to describe the generation of a fluorophore from non-fluorescent constituent parts via a so called "click reaction". In this case, the triazole ring forms an integral part of the fluorophore; i.e., a new property is imparted on a molecule conceived by a "click reaction".
14. Molander, G. A.; Ham, J. Org. Lett. 2006, 8, 2767-2770.
15. -3. Bond lengths (Å), angles (deg) and torsions (deg): N(1)-N(2) 1.3467-(13), N(2)-N(3) 1.3165(14), B(1)-O(1) 1.3664(16), N(1)-C(7) 1.4681-(15), B(1)-C(1) 1.5653(17); N(1)-N(2)-N(3) 107.12(9), O(1)-B(1)-C(1) 126.09(11); C(1)-C(6)-C(7)-N(1) 98.90, O(1)-B(1)-C(1)-C(6) 6.83.
16. Yuen, A. K. L.; Hutton, C. A. Tetrahedron Lett. 2005, 46, 7899-7903.
17. Perrin, D. D.; Dempsey, B. Buffers for pH and Metal Ion Control; Chapman and Hall: London 1974.
18. The K were analysed in Origin 7 using nonlinear (Levenberg-Marquardt algorithm) curve fitting. The errors reported are the standard errors obtained from the best fit.
19. Cooper, C. R.; James, T. D. J. Chem. Soc., Perkin Trans. 1 2000, 963-969.
20. Lorand, J. P.; Edwards, J. O. J. Org. Chem. 1959, 24, 769-774.
21. Edwards, N. Y.; Sager, T. W.; McDevitt, J. T.; Anslyn, E. V. J. Am. Chem. Soc. 2007, 129, 13575-13583.
22. The PENDANT technique results in primary and tertiary carbon atoms havid a different phase to secondary and quaternary carbon atoms. The phase is represented in the following manner: (+) positive phase; (-) negative phase. Homer, J.; Perry, M. C. J. Chem. Soc., Chem. Commun. 1994, 373-374.