Journal of the American Chemical Society
Communication
mechanism is unique, and we suggest that is the origin of the
excellent primary amine selectivity observed. We also
demonstrate that the emission maximum and the reaction
kinetics are easily tuned by making changes to the position
flanking the ylidenemalononitrile. Having a series of primary
amine reactive probes with different exchange rates might have
application in both real-time biosensing and array-based sensor
strategies, as we have already demonstrated their ability to label
the transferrin glycoprotein.
(10) For an example of a cis-enamine formation when an
̌
ylidenemalononitrile is treated with a primary amine: Skofic, P.;
Dambrot, C.; Kozelj, M.; Golobic, A.; Barrio, J. R.; Petric, A. Acta
Chim. Slov. 2005, 52, 391.
11) For an example of an amidine formation when an
̌
̌
̌
(
ylidenemalononitrile is treated with a primary amine: Lacroix, A.;
Fleury, J.-P. Tetrahedron Lett. 1978, 19, 3469.
(12) Binstead, R. A.; Jung, B.; Zuberbuhler, A. D. SPECFIT/32 global
analysis software, version 3.0.40 for 32-bit Windows systems; Spectrum
Software Associates: Marlborough, MA, 2007.
(13) (a) Maynor, M. S.; Nelson, T. L.; O’Sulliva, C.; Lavigne, J. J.
ASSOCIATED CONTENT
Supporting Information
Experimental procedures, spectroscopy data, and CIF files. This
Org. Lett. 2007, 9, 3217. (b) Gao, T.; Tillman, E. S.; Lewis, N. S. Chem.
Mater. 2005, 17, 2904.
■
*
S
(14) Medintz, I. L.; Pons, T.; Delehanty, J. B.; Susumu, K.; Brunel, F.
M.; Dawson, P. E.; Mattoussi, H. Bioconjugate Chem. 2008, 19, 1785.
AUTHOR INFORMATION
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
The authors thank the Clinton Health Access Initiative,
Corning Glass, Gates Foundation, and NSF (CHE-1152020)
for support.
REFERENCES
■
(
4
1) Wu, J.; Liu, W.; Ge, J.; Zhang, H.; Wang, P. Chem. Soc. Rev. 2011,
0, 3483.
(
2) (a) Morales, A. R.; Schafer-Hales, K. J.; Marcus, A. I.; Belfield, K.
D. Bioconjugate Chem. 2008, 19, 2559. (b) Meng, Q.; Yu, M.; Zhang,
H.; Ren, J.; Huang, D. Dyes Pigm. 2007, 73, 254. (c) Hoefelschweiger,
B. K.; Duerkop, A.; Wolfbeis, O. S. Anal. Biochem. 2005, 344, 122.
(
(
d) Banks, P. R.; Paquette, D. M. Bioconjugate Chem. 1995, 6, 447.
e) Mornet, D.; Ue, K. Biochemistry 1985, 24, 840.
(
3) (a) Yamaguchi, T.; Asanuma, M.; Nakanishi, S.; Saito, Y.;
Okazaki, M.; Dodo, K.; Sodeoka, M. Chem. Sci. 2014, 5, 1021.
(
(
b) Chan, J.; Dodani, S. C.; Chang, C. J. Nat. Chem. 2012, 4, 973.
c) Tynan, C. J.; Clarke, D. T.; Coles, B. C.; Rolfe, D. J.; Martin-
Fernandez, M. L.; Webb, S. E. D. PLoS One 2012, 7, e36265. (d) Jun,
M. E.; Roy, B.; Ahn, K. H. Chem. Commun. 2011, 47, 7583.
(
8
(
2
4) Soga, T.; Jimbo, Y.; Suzuki, K.; Citterio, D. Anal. Chem. 2013, 85,
973.
5) (a) Hettie, K. S.; Klockow, J. L.; Glass, T. E. J. Am. Chem. Soc.
014, 136, 4877. (b) Shi, L.; Fu, Y.; He, C.; Zhu, D.; Gao, Y.; Wang,
Y.; He, Q.; Cao, H.; Cheng, J. Chem. Commun. 2014, 50, 872. (c) Lee,
B.; Chen, S.; Heinis, C.; Scopelliti, R.; Severin, K. Org. Lett. 2013, 15,
3
456. (d) Wu, J.-S.; Liu, W.-M.; Zhuang, X.-Q.; Wang, F.; Wang, P.-F.;
Tao, S.-L.; Zhang, X.-H.; Wu, S.-K.; Lee, S.-T. Org. Lett. 2006, 9, 33.
e) Secor, K. E.; Glass, T. E. Org. Lett. 2004, 6, 3727. (f) Feuster, E. K.;
Glass, T. E. J. Am. Chem. Soc. 2003, 125, 16174.
6) (a) Ryu, D.; Park, E.; Kim, D.-S.; Yan, S.; Lee, J. Y.; Chang, B.-Y.;
(
(
Ahn, K. H. J. Am. Chem. Soc. 2008, 130, 2394. (b) Mohr, G. J. Anal.
Chim. Acta 2004, 508, 233. (c) Mertz, E.; Zimmerman, S. C. J. Am.
Chem. Soc. 2003, 125, 3424. (d) Mertz, E.; Beil, J. B.; Zimmerman, S.
C. Org. Lett. 2003, 5, 3127.
(
́
7) (a) Chatterjee, S.; Karuso, P.; Boulange, A.; Peixoto, P. a.; Franck,
X.; Datta, A. J. Phys. Chem. B 2013, 117, 14951. (b) Coghlan, D. R.;
Mackintosh, J. a.; Karuso, P. Org. Lett. 2005, 7, 2401. (c) Bell, P. J. L.;
Karuso, P. J. Am. Chem. Soc. 2003, 125, 9304.
(
8) Longstreet, A. R.; Campbell, B. S.; Gupton, B. F.; McQuade, D.
T. Org. Lett. 2013, 15, 5298.
9) Villemin, D.; Belhadj, Z.; Cheikh, N.; Choukchou-Braham, N.;
Bar, N.; Lohier, J.-F. Tetrahedron Lett. 2013, 54, 1664.
(
1
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