Journal of Inorganic and General Chemistry
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
–
H
Ar), 5.89 (s, 1 H, –HPh), 5.54 (d, J = 7.9 Hz, 1 H, –HAr), 1.54 (s, 2
H, –HPh), 0.40 (s, 1 H, –HAr), –1.49 (s, 9 H, Pz–CH ), –8.96 (s, 9 H,
Pz–CH ), –13.54 (s, 1 H, B–H) ppm. ATR-IR: ν˜ = 3072 (w), 2919
Keywords: Quercetinase; Flavonolate; O–O activation;
Nickel; Dioxygenation
3
3
(
(
(
(
7
4
6
w), 2509 (w, BH), 1606 (w), 1576 (w), 1544 (m), 1495 (w), 1477
m), 1463 (m), 1449 (m), 1434 (m), 1415 (s), 1385 (m), 1328 (s), 1303
w), 1280 (m), 1245 (s), 1196 (s), 1154 (m), 1129 (w), 1053 (m), 1017
m), 969 (m), 874 (w), 855 (m), 807 (m), 789 (m), 763 (s), 748 (m), References
12 (w), 703 (w), 689 (m), 650 (m), 641 (m), 586 (w), 540 (w),
–1
83 (m), 466 (m), 451 (w) cm . ESI/MS (MeCN, +): m/z =
[
1] S. Tranchimand, P. Brouant, G. Iacazio, Biodegradation 2010, 21,
+
31.1584 ([2+Na] , 100%) (calcd. 631.1577). C30
H31BN
6
NiO
2
S
833–859.
–1
(
(
609.18 g·mol ): C 58.59 (calcd. 59.15); H 5.16 (5.13); N 13.10
13.70); S 5.12 (5.26)%; concerning C deviation see comment above.
[2] a) B. Gopal, L. L. Madan, S. F. Betz, A. A. Kossiakoff, Biochem-
istry 2005, 44, 193–201; b) D. Nianios, S. Thierbach, L. Steimer,
P. Lulchev, D. Klostermeier, S. Fetzner, BMC Biochem. 2015, 16,
10; c) H. Merkens, R. Kappl, R. P. Jakob, F. X. Schmid, S.
Fetzner, Biochemistry 2008, 47, 12185–12196.
Synthesis of 3: This compound was synthesized in a similar manner
as described for the synthesis of [Tp*NiFla] 1 except for the usage of
[
3] J.-H. Jeoung, D. Nianios, S. Fetzner, H. Dobbek, Angew. Chem.
Int. Ed. 2016, 55, 3281–3284.
3
-hydroxyselenoflavone (67.8 mg, 225 μmol) instead of 3-hy-
droxyflavone. The complex was isolated as a brown solid (81.3 mg,
5% yield, 124 μmol). Crystals of 3 suitable for single-crystal X-ray
diffraction studies were obtained by layering a saturated solution of 3
in dichloromethane with MeCN. 1H NMR (400 MHz, CDCl
): δ =
3.80 (s, 3 H, Pz–H), 15.40 (s, 1 H, –HAr), 11.07 (s, 2 H, –HPh), 9.24
s, 1 H, –HAr), 6.19 (s, 2 H, –HPh), 6.03 (s, 1 H, –HAr), 4.79 (s, 1 H,
Ph), 0.74 (s, 1 H, –HAr), –1.26 (s, 9 H, Pz–CH ), –8.46 (s, 9 H,
[
4] a) S. Hoof, M. Sallmann, C. Herwig, B. Braun-Cula, C. Limberg,
Dalton Trans. 2017, 46, 16792–16795; b) P. Holze, T. Corona, N.
Frank, B. Braun-Cula, C. Herwig, A. Company, C. Limberg, An-
gew. Chem. Int. Ed. 2017, 56, 2307–2311.
5
3
6
(
–
[
[
5] M. Sallmann, C. Limberg, Acc. Chem. Res. 2015, 48, 2734–2743.
6] A. W. Addison, T. N. Rao, J. Reedijk, J. van Rijn, G. C. Ver-
schoor, J. Chem. Soc., Dalton Trans. 1984, 1349–1356.
H
3
Pz–CH
3
), –13.20 (s, 1 H, B–H) ppm. ATR-IR: ν˜ = 3071 (w), 2952 [7] a) Y.-J. Sun, Q.-Q. Huang, J.-J. Zhang, Dalton Trans. 2014, 43,
(
(
(
(
(
5
w), 2918 (w), 2512 (m, BH), 1607 (m), 1566 (m), 1544 (m), 1492
6480–6489; b) Y.-J. Sun, Q.-Q. Huang, T. Tano, S. Itoh, Inorg.
Chem. 2013, 52, 10936–10948; c) A. Matuz, M. Giorgi, G.
Speier, J. Kaizer, Polyhedron 2013, 63, 41–49; d) K. Grubel, K.
Rudzka, A. M. Arif, K. L. Klotz, J. A. Halfen, L. M. Berreau, In-
org. Chem. 2010, 49, 82–96.
w), 1471 (m), 1459 (m), 1434 (m), 1406 (s), 1384 (m), 1330 (s), 1312
m), 1300 (m), 1274 (m), 1243 (s), 1192 (s), 1150 (m), 1126 (m), 1096
m), 1057 (m), 1039 (m), 1012 (m), 984 (m), 951 (m), 855 (m), 808
m), 779 (m), 755 (m), 744 (m), 693 (m), 681 (m), 642 (s), 634 (s),
[
8] a) T. Oka, F. J. Simpson, H. G. Krishnamurty, Can. J. Microbiol.
–1
76 (m), 482 (w), 465 (m), 437 (m) cm . ESI/MS (MeCN, +): m/z
1
972, 18, 493–508; b) G. Speier, in Studies in Surface Science
and Catalysis, Book Series, vol. 66 (Ed.: L. I. Simándi), Elsevier,
991, pp. 269–278.
+
=
6 2
679.1020 ([3+Na] , 100%) (calcd. 679.1018). C30H31BN NiO Se
–1
(
(
656.07 g·mol ): C 53.51 (calcd. 54.92); H 4.61 (4.76); N 12.94
12.81)%; concerning C deviation see comment above.
1
[9] a) S. Fetzner, Appl. Environ. Microbiol. 2012, 78, 2505–2514; b)
C. J. Allpress, L. M. Berreau, Coord. Chem. Rev. 2013, 257,
Synthesis of 3-Hydroxy-4-selenoflavone: 3-Hydroxyflavone
200 mg, 840 μmol) was dissolved in toluene (20 mL) and Woollins
reagent (PhPSe (250 mg, 470 μmol) was added. The reaction mix-
ture was stirred for 12 h at 80 °C and all volatiles were removed in
3005–3029.
(
[
10] F. Fusetti, K. H. Schroter, R. A. Steiner, P. I. van Noort, T. Pijn-
ing, H. J. Rozeboom, K. H. Kalk, M. R. Egmond, B. W. Dijkstra,
Structure 2002, 10, 259–268.
2 2
)
vacuo. The residue was dissolved in DCM and filtered through a short [11] a) R. A. Steiner, K. H. Kalk, B. W. Dijkstra, Proc. Natl. Acad.
silica column. The solvent was removed in vacuo and the residue
recrystallized from EtOH to give the product (220 mg, 87% yield,
Sci. USA 2002, 99, 16625–16630; b) R. A. Steiner, I. M. Kooter,
B. W. Dijkstra, Biochemistry 2002, 41, 7955–7962.
[12] J. V. Valente, M. A. Buntine, S. F. Lincoln, A. David Ward, Inorg.
Chim. Acta 2007, 360, 3380–3386.
13] a) A. D. Burrows, R. W. Harrington, M. F. Mahon, S. J. Teat,
Cryst. Growth Des. 2004, 4, 813–822; b) L. S. Maffett, K. L.
Gunter, K. A. Kreisel, G. P. A. Yap, D. Rabinovich, Polyhedron
30 μmol) as a red-brown solid. 1H NMR (400 MHz, CDCl
7
8
1
1
3
): δ =
.80 (s, 1 H, -OH), 8.61 (dd, J = 8.3, 1.2 Hz, 1 H), 8.48 (dd, J = 8.3,
.6 Hz, 2 H), 7.81 (ddd, J = 8.6, 7.0, 1.6 Hz, 1 H), 7.68 (dd, J = 8.6,
[
.1 Hz, 1 H), 7.62–7.47 (m, 4 H) ppm. 13C NMR (101 MHz, CDCl
):
3
δ = 190.26, 150.31, 149.45,133.20, 131.57, 131.37, 131.29, 129.15,
2
007, 26, 4758–4764; c) E. Ramachandran, D. S. Raja, J. L.
1
1
1
28.93, 126.80, 118.64, 77.16 ppm. ATR-IR: ν˜ = 3039, 1688, 1602,
Mike, T. R. Wagner, M. Zeller, K. Natarajan, RSC Adv. 2012, 2,
581, 1568, 1530, 1487, 1457, 1410, 1327, 1303, 1289, 1262, 1242,
8515–8525.
–1
214, 1190, 1163, 1146, 1118, 1095, 1067, 1042, 1027 cm . ESI/MS
[14] CSD version 5.39, Nov 2017 was used to carry out the search.
The average bond lengths were located as outlined in: J.
van de Streek, Acta Crystallogr., Sect. B: Struct. Sci. 2006, 62,
+
(MeCN, +): m/z = 323.9680 ([SeFlavone+Na] , 25%) (calcd.
323.9666).
567–579.
Supporting Information (see footnote on the first page of this article):
Supporting Information contain additional crystallographic data for
[15] D. W. S. Westlake, J. M. Roxburgh, G. Talbot, Nature 1961, 189,
510.
1
(CCDC 1873875), 2 (CCDC 1873876) and 3 (CCDC 1873877), 1H
[16] A. L. Maçanita, F. Elisei, G. G. Aloisi, F. Ortica, V. Bonifácio,
A. Dias, E. Leitão, M. J. Caldeira, C. D. Maycock, R. S. Becker,
Photochem. Photobiol. 2003, 77, 22–29.
NMR and ATR-IR spectra.
[
17] R. Santi, A. M. Romano, A. Sommazzi, M. Grande, C. Bianchini,
Acknowledgements
G. Mantovani, J. Mol. Catal. A 2005, 229, 191–197.
We are grateful to the Humboldt-Universität zu Berlin for financial
support and the cluster of excellence UniCat for valuable discussions.
Received: October 21, 2018
Published online:
Z. Anorg. Allg. Chem. 0000, 0–0
www.zaac.wiley-vch.de
5
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