Organic Letters
Letter
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Scheme 5. One-Pot Disulfide Rebridging of sCT with
Functional Divinylsulfonamides
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functional divinylsulfonamides provide opportunities for the
specific introduction of various functionalities, including affinity
probes, fluorescent tags, and drugs, into peptides. In addition,
given the successful insertion of a linkable group, such as an
alkyne at a specific position, our method also provides an
attractive tool for selectively modifying peptides. We will report
on further developments and applications involving this powerful
new class of reagents.
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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S
(12) Griebenow, N.; Dilmac,
Chem. 2016, 27, 911.
̧ A. M.; Greven, S.; Brase, S. Bioconjugate
̈
Experimental details, characterization data, and NMR
spectra for all new compounds (PDF)
(13) Wilson, P.; Anastasaki, A.; Owen, M. R.; Kempe, K.; Haddleton,
D. M.; Mann, S. K.; Johnston, A. P.; Quinn, J. F.; Whittaker, M. R.;
Hogg, P. J.; Davis, T. P. J. Am. Chem. Soc. 2015, 137, 4215.
(14) Brown, S. P.; Smith, A. B. J. Am. Chem. Soc. 2015, 137, 4034.
(15) Spokoyny, A. M.; Zou, Y.; Ling, J. J.; Yu, H.; Lin, Y. S.; Pentelute,
B. L. J. Am. Chem. Soc. 2013, 135, 5946.
AUTHOR INFORMATION
Corresponding Authors
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(16) Assem, N.; Ferreira, D. J.; Wolan, D. W.; Dawson, P. E. Angew.
Chem., Int. Ed. 2015, 54, 8665.
ORCID
(17) Dadova, J.; Orsag, P.; Pohl, R.; Brazdova, M.; Fojta, M.; Hocek, M.
Angew. Chem., Int. Ed. 2013, 52, 10515.
(18) (a) Furman, J. L.; Kang, M.; Choi, S.; Cao, Y.; Wold, E. D.; Sun, S.
B.; Smider, V. V.; Schultz, P. G.; Kim, C. H. J. Am. Chem. Soc. 2014, 136,
8411. (b) Suh, E. H.; Liu, Y.; Connelly, S.; Genereux, J. C.; Wilson, I. A.;
Kelly, J. W. J. Am. Chem. Soc. 2013, 135, 17869.
(19) Collins, J.; Tanaka, J.; Wilson, P.; Kempe, K.; Davis, T. P.;
McIntosh, M. P.; Whittaker, M. R.; Haddleton, D. M. Bioconjugate
Chem. 2015, 26, 633.
(20) (a) Vinogradov, A. A.; Choo, Z. N.; Totaro, K. A.; Pentelute, B. L.
Org. Lett. 2016, 18, 1226. (b) Lautrette, G.; Touti, F.; Lee, H. G.; Dai, P.;
Pentelute, B. L. J. Am. Chem. Soc. 2016, 138, 8340.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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This work was supported by the National Natural Science
Foundation of China (NFSC; No. 21502114), China Post-
doctoral Science Foundation (No. 2015M581677), and the
Open Foundation of the State Key Laboratory of Drug Research,
China (No. SIMM1601KF-05).
(21) Robin, M. P.; Wilson, P.; Mabire, A. B.; Kiviaho, J. K.; Raymond, J.
E.; Haddleton, D. M.; O’Reilly, R. K. J. Am. Chem. Soc. 2013, 135, 2875.
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