Page 7 of 7
Organic & Biomolecular Chemistry
Please do not adjust margins
Journal Name
ARTICLE
isomer specific effects. Therefore, the switching moiety was
placed in ortho position increasing on one hand inhibitory
activity and on the other hand isomer dependent effects.
Compound 37 could be identified as a highly inhibitory active
photochromic PETG‐derivative with 5‐fold difference upon
switching and a Ki value of 60 nM (trans‐isomer). However, the
isomer‐specific difference in activity has to be further improved
before starting single molecule studies. Additional docking
analysis explained the experimental observations.
DOI: 10.1039/C8OB02122H
Gelder, R. H. Kramer, Neuron, 2012, 75, 271‐282.
20 I. Tochitsky, A. Polosukhina, V. E. Degtyar, N. Gallerani, C. M.
Smith, A. Friedman, R. N. van Gelder, D. Trauner, D. Kaufer, R.
H. Kramer, Neuron, 2014, 81, 800‐813.
21 N. A. Simeth, A. C. Kneuttinger, R. Sterner, B. König, Chem. Sci.,
2017, 8, 6474‐6483.
22 N. A. Simeth, L. M. Altmann, N. Wössner, E. Bauer, M. Jung, B.
König, J. Org. Chem., 2018, 83, 7919‐7927.
23 B. Eisel, F. Hartrampf, T. Meier, D. Trauner, FEBS Lett., 2018,
592, 343‐355.
24 D. Wilson, J. W. Li, N. R. Branda, ChemMedChem, 2017, 12
,
284‐287.
Conflicts of interest
25 R. Ferreira, J. R. Nilsson, C. Solano, J. Andréasson, M. Grøtli,
There are no conflicts to declare.
Sci. Rep., 2015, 5, 9769‐9776.
26 J. Broichhagen, I. Jurastow, K. Iwan, W. Kummer, D. Trauner,
Angew. Chem. Int. Ed., 2014, 53, 7657‐7660.
27 D. Wutz, D. Gluhaceic, A. Chakrabarti, K. Schmidtkunz, D.
Robaa, F. Erdmann, C. Romier, W. Sippl, M. Jung, B. König,
Org. Biomol. Chem., 2017, 15, 4882‐4896.
28 D. H. Juers, B. W. Matthews, R. E. Huber, Protein Science,
2012, 21, 1792‐1807.
Acknowledgements
KR and BK thank the ERASynBio grant (MODULIGHTOR) (PCIN‐
2015‐163‐C02‐01) for financial support. KR thanks Josef
Kiermaier and Wolfgang Söllner for mass spectrometry analysis.
HHG thanks the DFG for a Heisenberg Fellowship (grant GO
1968/5‐1).
29 Q. Husain, Crit. Rev. Biotechnol., 2010, 30, 41‐62.
30 P. Mogalisetti, H. H. Gorris, M. J. Rojek, D. R. Walt, Chem. Sci.,
2014, 5, 4467‐4473.
31 M. J. Mickert, H. H. Gorris, J. Phys. Chem. B, 2018, 122, 5809‐
5819.
32 A. G. Hadd, D. E. Raymond, J. W. Halliwell, S. C. Jacobson, J. M.
Ramsey, Anal. Chem., 1997, 69, 3407‐3412.
Notes and references
1
2
3
4
5
6
7
8
W. A. Velema, W. Szymanski, B. L. Feringa, J. Am. Chem. Soc.,
2014, 136, 2178‐2191.
33 R. E. Huber, M. T. Gaunt, Can. J. Biochem., 1982, 60, 608‐612.
34 R. B. Liebherr, A. Hutterer, M. J. Mickert, F. C. Vogl, A. Beutner,
A. Lechner, H. Hummel, H. H. Gorris, Anal. Bioanal. Chem.,
2015, 407, 7443‐7452.
D. Bléger and S. Hecht, Angew. Chem. Int. Ed., 2015, 54
,
11338‐11349.
W. Szymanski, J. M. Beierle, H. A. V. Kistemaker, W. A. Velema,
B. L. Feringa, Chem. Rev., 2013, 113, 6114‐6178.
35 M. Kleban, P. Hilgers, J. N. Greul, R. D. Kugler, J. Li, S. Picasso,
M. M. Lerch, M. J. Hansen, G. M. van Dam, W. Szymanski, B.
L. Feringa, Angew. Chem. Int. Ed., 2016, 55, 10987‐10999.
C. Brieke, F. Rohrbach, A. Gottschalk, G. Mayer, A. Heckel,
Angew. Chem. Int. Ed., 2012, 51, 8446‐8476.
P. Vogel, V. Jäger, ChemBioChem, 2001, 2, 365‐368.
36 J. N. Greul, M. Kleban, B. Schneider, S. Picasso, V. Jäger,
ChemBioChem, 2001, , 368‐370.
2
37 H. H. Gorris, D. M. Rissin, D. R. Walt, PNAS, 2007, 104, 17680‐
17685.
M. M. Lerch, M. J. Hansen, W. A. Velema, W. Szymanski, B. L.
Feringa, Nat. Commun., 2016, 7, 12054.
38 E. Mitscherlich, Ann. Pharm. 1834, 12, 311‐314.
39 G. S. Hartley, Nature 1937, 140, 281‐282.
40 L. Lindner, P. Klüfers, Z. Anorg. Allg. Chem., 2015, 641, 1869‐
1873.
H. Bouas‐Laurent and H. Dürr, Pure Appl. Chem., 2001, 73
,
639‐665.
P. Klán, T. Šolomek, C. G. Bochet, A. Blanc, R. Givens, M.
Rubina, V. Popik, A. Kostikov, J. Wirz, Chem. Rev., 2013, 113
,
41 M. P. Seed, M. Burnet, H. J. Gutcke, Assignee Diosamine
119‐191.
Development Corporation Patent, 2008, WO2008059003 A1
.
9
M. M. Lerch, W. Szymanski, B. L. Feringa, Chem. Soc. Rev.,
2018, 47, 1910‐1937.
42 R. Rajaganesh, A. Gopal, T. M. Das, A. Ajayaghosh, Org. Lett.,
2012, 14, 748‐751.
10 J. Garcia‐Amorós, M. Díaz‐Lobo, S. Nonell, D. Velasco, Angew.
Chem. Int. Ed., 2012, 51, 12820‐12823.
11 J. Garcia‐Amorós, M. C. R. Castro, P. Coelho, M. M. M. Raposo,
D. Velasco, Chem. Commun., 2013, 49, 11427‐11429.
12 J. Garcia‐Amorós, S. Nonell, D. Velasco, Chem. Commun.,
2012, 48, 3421‐3423.
43 A. G. Watts, T. Kantner, A. B. MacKenzie, Assignee The
University of Bath, 2010, WO2010070300A2
.
44 L. M. Doyle, S. O’Sullivan, C. Di Salvo, M. McKinney, P.
McArdle, P. V. Murphy, Org. Lett., 2017, 19, 5802‐5805.
45 X. Xiao, Y. Zhao, P. Shu, X. Zhao, Y. Liu, J. Sun, Q. Zhang, J. Zeng,
Q. Wan, J. Am. Chem. Soc., 2016, 138, 13402‐13407.
13 H. Kaufman, S. M. Vratsanos, B. F. Erlanger, Science, 1968,
162, 1487‐1489.
46 X. Li, L. Huang, X. Hu, X. Huang, Org. Biomol. Chem., 2009,
7
,
117‐127.
14 W. J. Deal, B. F. Erlanger, D. Nachmansohn, Proc. Natl. Acad.
Sci. U. S. A., 1969, 64, 1230‐1234.
47 H. Wang, S. Sun, J. Cheng, Tetrahedron Letters, 2017, 58
,
3875‐3878.
15 M. Volgraf, P. Gorostiza, R. Numano, R. H. Kramer, E. Y.
48 M. Poláková, S. Šesták, E. Lattová, L. Petruš, J. Mucha, I.
Tvaroška, J. Kóňa, Eur. J. Med. Chem., 2011, 46, 944‐952.
49 D. Zhao, M. Johansson, J.‐E. Bäckvall, Eur. J. Org. Chem., 2007,
26, 4431‐4436.
50 N. Marquestaut, A. Martin, D. Talaga, L. Servant, S. Ravaine, S.
Reculusa, D. M. Bassani, E. Gillies, F. Lagugné‐Labarthet,
Langmuir, 2008, 24, 11313‐11321.
Isacoff, D. Trauner, Nat. Chem. Biol., 2006, 2, 47‐52.
16 P. Gorostiza, M. Volgraf, R. Numano, S. Szobota, D. Trauner,
E. Y. Isacoff, Proc. Natl. Acad. Sci. U. S. A., 2007, 104, 10865‐
10870.
17 M. Volgraf, P. Gorostiza, S. Szobota, M. R. Helix, E. Y. Isacoff,
D. Trauner, J. Am. Chem. Soc., 2007, 129, 260‐261.
18 M. Wegener, M. J. Hansen, A. J. M. Driessen, W. Szymanski, B.
L. Feringa, J. Am. Chem. Soc., 2017, 139, 17979‐17986.
51 O. Trott, A. J. Olson, J. Comput. Chem., 2010, 31, 455‐461.
52 E. Krieger, G. Vriend, Bioinformatics, 2014, 30, 2981‐2982.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1‐3 | 7
Please do not adjust margins