Organic Letters
Letter
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9) Jana, A.; Atta, S.; Sarkar, S. K.; Singh, N. D. P. Tetrahedron 2010, 66,
Scheme 3. Stepwise Photorelease of Bimane Caged Ester with
Two Different Carboxylic Acids (12)
9
798−9807.
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136.
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M.; Unash, R.; Smith, E. A.; Winter, A. H. J. Am. Chem. Soc. 2015, 137,
(
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3
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783−3786.
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Antony, L. A. P.; Klan
́
, P.; Wirz, J. J. Org. Chem. 2013, 78, 1833−1843.
carboxylic acids from bimane caged esters (7a−g, 12), which was
supported by high-resolution mass spectroscopy (HRMS). After
photoirradiation for 60 min, the reaction mixture was subjected
to HRMS, and it was found that all the possible intermediates for
the stepwise mechanism were present in the reaction mixture
along with released carboxylic acids (see Figures S23 and S24 in
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15) Lehar, J.; Krueger, A. S.; Avery, W.; Heilbut, A. M.; Johansen, L.
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66.
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17) Kosower, N. S.; Newton, G. L.; Kosower, E. M.; Ranney, H. M.
In summary, we have successfully synthesized single and dual
(
same and different) component caged esters based on bimane
(
for carboxylic and amino acids with interesting photophysical
and photochemical properties. The FPRPGs unmasked their
corresponding carboxylic and amino acids on exposure to visible
light (≥410 nm). Moreover, the release of two different
carboxylic acids from single FPRPG was achieved, which will
be useful in various applications. In the future, we wish to design a
dual drug delivery system using our FPRPG, which will enable us
to release two different drugs simultaneously by visible light.
Biochim. Biophys. Acta, Protein Struct. 1980, 622, 201−209.
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(
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4
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ASSOCIATED CONTENT
Supporting Information
■
Phys. Chem. 1981, 85, 2766−2771.
(23) Schmidt, R.; Geissler, D.; Hagen, V.; Bendig, J. J. Phys. Chem. A
*
S
2
007, 111, 5768−5774.
24) Jana, A.; Nguyen, K. T.; Li, X.; Zhu, P.; Tan, N. S.; Ågren, H.;
Zhao, Y. ACS Nano 2014, 8, 5939−5952.
(
Synthesis details, characterization data, and other
experimental details (PDF)
AUTHOR INFORMATION
■
ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
We thank DST (SERB) for financial support and DST-FIST for
00 and 400 MHz NMR. A.C. is thankful to UGC-New Delhi for
■
6
fellowship. Y.V. is thankful to IIT Kharagpur for fellowship.
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