Angewandte Chemie International Edition
10.1002/anie.201711935
COMMUNICATION
Mata, N. W. Luedtke, J. Am. Chem. Soc. 2015, 137, 699-707; h) G.
Mata, O. P. Schmidt, N. W. Luedtke, Chem. Commun. 2016, 52, 4718-
[17] E. Balducci, M. Emanuelli, N. Raffaelli, S. Ruggieri, A. Amici, G. Magni,
G. Orsomando, V. Polzonetti, P. Natalini, Anal. Biochem. 1995, 228,
64-68.
4
721; i) A. Nuthanakanti, M. A. Boerneke, T. Hermann, S. G. Srivatsan,
Angew. Chem. Int. Ed. 2017, 56, 2640-2644.
[18] T. G. Scott, R. D. Spencer, N. J. Leonard, G. Weber, J. Am. Chem.
Soc. 1970, 92, 687-695.
[
6]
a) N. J. Greco, Y. Tor, J. Am. Chem. Soc. 2005, 127, 10784-10785; b)
R. W. Sinkeldam, N. J. Greco, Y. Tor, ChemBioChem 2008, 9, 706-
[19] a) K. Suzuki, H. Nakano, S. Suzuki, J. Biol. Chem. 1967, 242, 3319-
3325; b) W. Ying, Antioxid. Redox Signal. 2008, 10, 179-206.
[20] a) F. Lerner, M. Niere, A. Ludwig, M. Ziegler, Biochem. Biophys. Res.
Commun. 2001, 288, 69-74; b) S. Garavaglia, A. Galizzi, M. Rizzi, J.
Bacteriol. 2003, 185, 4844-4850.
7
1
1
09; c) Y. Xie, A. V. Dix, Y. Tor, J. Am. Chem. Soc. 2009, 131, 17605-
7614; d) Y. Xie, T. Maxson, Y. Tor, J. Am. Chem. Soc. 2010, 132,
1896-11897; e) R. W. Sinkeldam, A. J. Wheat, H. Boyaci, Y. Tor,
Chemphyschem 2011, 12, 567-570.
[
[
[
7]
8]
9]
D. Shin, R. W. Sinkeldam, Y. Tor, J. Am. Chem. Soc. 2011, 133,
[21] a) A. Ronneberg, G. Metz, R. Weld, P. Roffey, C. Craney, J. Labelled
Compd. Radiopharm. 1992, 31, 329-332; b) A. Ochiai, S. Mori, S.
Kawai, K. Murata, Protein Expr. Purif. 2004, 36, 124-130; c) K. Ohashi,
S. Kawai, M. Koshimizu, K. Murata, Mol. Cell. Biochem. 2011, 355, 57-
64.
1
4912-14915.
a) A. R. Rovira, A. Fin, Y. Tor, J. Am. Chem. Soc. 2015, 137, 14602-
4605; b) A. R. Rovira, A. Fin, Y. Tor, Chem. Sci. 2017, 8, 2983-2993.
1
a) R. W. Sinkeldam, L. S. McCoy, D. Shin, Y. Tor, Angew. Chem. Int.
Ed. 2013, 52, 14026-14030; b) W. Liu, D. Shin, Y. Tor, B. S.
Cooperman, ACS Chem. Biol. 2013, 8, 2017-2023; c) R. A. Mizrahi, D.
Shin, R. W. Sinkeldam, K. J. Phelps, A. Fin, D. J. Tantillo, Y. Tor, P. A.
Beal, Angew. Chem. Int. Ed. 2015, 54, 8713-8716; d) M. Sholokh, R.
Improta, M. Mori, R. Sharma, C. Kenfack, D. Shin, K. Voltz, R. H. Stote,
O. A. Zaporozhets, M. Botta, Y. Tor, Y. Mély, Angew. Chem. Int. Ed.
[22] S. W. Cho, J. G. Joshi, Neuroscience 1990, 38, 819-828.
[23] I. Carlberg, B. Mannervik, Methods Enzymol. 1985, 113, 484-490.
[24] A. Meister, M. E. Anderson, Annu. Rev. Biochem 1983, 52, 711-760.
[25] a) C. Moreau, G. K. Wagner, K. Weber, A. H. Guse, B. V. L. Potter, J.
Med. Chem. 2006, 49, 5162-5176; b) Y. Wang, D. Rösner, M. Grzywa,
A. Marx, Angew. Chem. Int. Ed. 2014, 53, 8159-8162.
2
016, 55, 7974-7978; e) Y. Li, A. Fin, L. McCoy, Y. Tor, Angew. Chem.
Int. Ed. 2017, 56, 1303-1307.
10] a) H. Otomo, S. Park, S. Yamamoto, H. Sugiyama, RSC Adv. 2014, 4,
1341-31344; b) S. Park, H. Otomo, L. Zheng, H. Sugiyama, Chem.
[
[
3
Commun. 2014, 50, 1573-1575; c) J. H. Han, S. Yamamoto, S. Park, H.
Sugiyama, Chem. Eur. J. 2017, 23, 7607-7613.
11] a) P. K. Samanta, A. K. Manna, S. K. Pati, J. Phys. Chem. B 2012, 116,
7
618-7626; b) Y.-J. Lee, Y. H. Jang, Y. Kim, S. Hwang, Bull. Korean
Chem. Soc. 2012, 33, 4255-4257; c) M. Gedik, A. Brown, J.
Photochem. Photobiol. A: Chem. 2013, 259, 25-32; d) P. K. Samanta,
S. K. Pati, New J. Chem. 2013, 37, 3640; e) P. K. Samanta, S. K. Pati,
Phys. Chem. Chem. Phys. 2015, 17, 10053-10058; f) M. Chawla, R.
Credendino, E. Chermak, R. Oliva, L. Cavallo, J. Phys. Chem. B 2016,
1
20, 2216-2224; g) M. Chawla, A. Poater, R. Oliva, L. Cavallo, Phys.
Chem. Chem. Phys. 2016, 18, 18045-18053; h) L. Zhang, X. Kong, M.
Wang, M. Zheng, Int. J. Quantum Chem. 2017, 117, e25377.
[
12] a) J. R. Barrio, J. A. Secrist, N. J. Leonard, Proceedings of the National
Academy of Sciences 1972, 69, 2039-2042; b) N. J. Leonard, J. R.
Barrio, Crit. Rev. Biochem. 1984, 15, 125-199; c) G. Pergolizzi, J. N.
Butt, R. P. Bowater, G. K. Wagner, Chem. Commun. 2011, 47, 12655-
1
2657; d) T. Noguchi, A. Dawn, D. Yoshihara, Y. Tsuchiya, T.
Yamamoto, S. Shinkai, Macromol. Rapid Commun. 2013, 34, 779-784;
e) J. Wierzchowski, J. M. Antosiewicz, D. Shugar, Mol. Biosyst. 2014,
1
0, 2756-2774.
[
13] a) C. Vranken, A. Fin, P. Tufar, J. Hofkens, M. D. Burkart, Y. Tor, Org.
Biomol. Chem. 2016, 14, 6189-6192; b) A. R. Rovira, A. Fin, Y. Tor, J.
Am. Chem. Soc. 2017, 139, 15556-15559.
tz
[
[
[
14] We will provide samples of ATP upon request
15] See SI for additional experimental procedures and data.
16] a) N. Raffaelli, L. Sorci, A. Amici, M. Emanuelli, F. Mazzola, G. Magni,
Biochem. Biophys. Res. Commun. 2002, 297, 835-840; b) L. Chen, R.
Petrelli, K. Felczak, G. Gao, L. Bonnac, J. S. Yu, E. M. Bennett, K. W.
Pankiewicz, Curr. Med. Chem. 2008, 15, 650-670.
This article is protected by copyright. All rights reserved.