T.-K. Kim et al. / Tetrahedron Letters 49 (2008) 4879–4881
4881
In summary, we have developed a chemosensor (1) based on a
coumarin with an aldehyde functionality. The sensor selectively
reacted with Hcy or Cys via a thiazinane or thiazolidine ring in a
polar protic solvent. Its fluorescence was faded out due to a PET
from a neighboring nitrogen atom of the thiazinane/thiazolidine
ring. Sensor 1 showed a high selectivity and affinity toward Hcy
or Cys over other amino acids. This selectivity could be easily
observed in a naked eye using a fluorescence microscope. Further
study on the Hcy/Cys sensor via the thiazinane/thiazolidine forma-
tion in water is on the progress.
2. Seshadri, S.; Beiser, A.; Selhub, J.; Jacques, P. F.; Rosenberg, I. H.; D’Agostino, R.
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Wang, W.; Rusin, O.; Xu, X.; Kim, K. K.; Escobedo, J. O.; Fakayode, S. O.; Fletcher,
K. A.; Lowry, M.; Schowalter, C. M.; Lawrence, C. M.; Fronczek, F. R.; Warner, I.
M.; Strongin, R. M. J. Am. Chem. Soc. 2005, 127, 15949; (c) Zhang, D. Q.; Zhang,
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(a) Tanaka, F.; Mase, N.; Barbas, C. F., III. Chem. Commun. 2004, 15, 1762; (b)
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Acknowledgements
Financial supports of this work from the Korean Science and
Engineering Foundation for the Scientists Exchange Program
1
29, 10322; (d) Tang, B.; Xing, Y.; Li, P.; Zhang, N.; Yu, F.; Yang, G. J. Am. Chem.
Soc. 2007, 129, 11666; (e) Bouffard, J.; Kim, Y.; Swager, T. M.; Weissleder, R.;
Hilderbrand, S. A. Org. Lett. 2008, 10, 37; (f) Chen, H.; Zhao, Q.; Wu, Y.; Li, F.;
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(
Grant F03-2008-000-10027-0) and 2007 Kyonggi University Spe-
cialization Program are gratefully acknowledged.
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(a) Lee, K.-S.; Lee, J. T.; Hong, J.-I.; Kim, H.-J. Chem. Lett. 2007, 36, 816; (b) Lee,
K.-S.; Kim, H.-J.; Kim, G.-H.; Shin, I.; Hong, J.-I. Org. Lett. 2008, 10, 49.
Supplementary data
9. (a) Chin, J.; Kim, D. C.; Kim, H.-J.; Panosyan, F. B.; Kim, K. M. Org. Lett. 2004, 6,
2591; (b) Kim, K. M.; Park, H.; Kim, H.-J.; Chin, J.; Nam, W. Org. Lett. 2005, 7,
3525; (c) Kim, H.-J.; Kim, W.; Lough, A. J.; Kim, B. M.; Chin, J. J. Am. Chem. Soc.
2005, 127, 16776; (d) Kim, H.-J.; Kim, H.; Alhakimi, G.; Jeong, E. J.; Thavarajah,
Experimental data including NMR/mass for 1, fluorescence
titration and competition graphs, and Job’s plot for 1–Hcy (PDF).
N.; Studnicki, L.; Koprianiuk, A.; Lough, A. J.; Suh, J.; Chin, J. J. Am. Chem. Soc.
005, 127, 16370.
2
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11. The ring formation was too slow (
pH 7.4).
s1/2 ꢀ 8 h) in aqueous HEPES buffer (50 mM,
References and notes
12. When D O was added to 1-Hcy, the thiazinane was reverted to free 1 and Hcy.
2
Therefore, the reaction was assumed to be reversible and we called 1 as a
sensor.
1
.
(a) Wood, Z. A.; Schröder, E.; Harris, J. R.; Poole, L. B. Trends Biochem. Sci. 2003,
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