UPDATES
Laccase/2,2,6,6-Tetramethylpiperidinoxyl Radical (TEMPO)
[12] For selected recent publications, see: a) S. France, A.
Weatherwax, A. E. Taggi, T. Lectka, Acc. Chem. Res.
2004, 37, 592–600; b) L.-S. Wang, H.-C. Chen, Z.-C.
Xiong, X.-B. Pang, C.-D. Xiong, Macromol. Mater. Eng.
2010, 295, 381–385; c) W. R. H. Wright, R. Palkovits,
ChemSusChem 2012, 5, 1657–1667; d) P. Azadi, R.
Carrasquillo-Flores, Y. J. Pagꢁn-Torres, E. I. Gꢇrbꢇz, R.
Farnood, J. A. Dumesic, Green Chem. 2012, 14, 1573–
1576; e) D. M. Alonso, S. G. Wettstein, J. A. Dumesic,
Green Chem. 2013, 15, 584–595.
c) P. Gamez, I. W. C. E. Arends, R. A. Sheldon, J.
Reedijk, Adv. Synth. Catal. 2004, 346, 805–811; d) D.
Geisslmeir, W. G. Jary, H. Falk, Monatsh. Chem. 2005,
136, 1591–1599; e) N. Jiang, A. J. Ragauskas, J. Org.
Chem. 2006, 71, 7087–7090; f) S. Mannam, S. K. Alam-
setti, G. Sekar, Adv. Synth. Catal. 2007, 349, 2253–2258;
g) P. J. Figiel, A. Sibaouih, J. U. Ahmad, M. Nieger,
M. T. Rꢅisanen, M. Leskelꢅ, T. Repo, Adv. Synth.
Catal. 2009, 351, 2625–2632.
[21] P. Gamez, I. W. C. E. Arends, J. Reedijk, R. A. Shel-
[13] For reviews dealing with applications of laccases in bio-
technology and organic chemistry, see: a) S. Riva,
Trends Biotechnol. 2006, 24, 219–226; b) S. R. Couto,
J. L. T. Herrera, Biotechnol. Adv. 2006, 24, 500–513;
c) S. Witayakran, A. J. Ragauskas, Adv. Synth. Catal.
2009, 351, 1187–1209; d) T. Kudanga, G. S. Nyanhongo,
G. M. Guebitz, S. Burton, Enzyme Microb. Technol.
2011, 48, 195–208; e) Z. Yang, Synlett 2012, 23, 2574–
2575; f) M. Mogharabi, M. A. Faramarzi, Adv. Synth.
Catal. 2014, 356, 897–927.
[14] A. Dꢀaz-Rodrꢀguez, I. Lavandera, S. Kanbak-Aksu,
R. A. Sheldon, V. Gotor, V. Gotor-Fernꢁndez, Adv.
Synth. Catal. 2012, 354, 3405–3408.
[15] A. C. Herath, J. Y. Becker, Electrochim. Acta 2008, 53,
4324–4330.
don, Chem. Commun. 2003, 2414–2415.
[22] For methods with PdACTHNUGRTNE(NUG OAc)2: a) T. Nishimura, T.
Onoue, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64,
6750–6755; b) G.-J. Brink, I. W. C. E. Arends, M. Hoo-
genraad, G. Verspui, R. A. Sheldon, Adv. Synth. Catal.
2003, 345, 1341–1352; for methods with Ru-based cata-
lysts, see: c) A. Dijksman, A. Marino-Gonzꢁlez, A. M.
Payeras, I. W. C. E. Arends, R. A. Sheldon, J. Am.
Chem. Soc. 2001, 123, 6826–6833; d) Y. Endo, J.-E.
Bꢅckvall, Chem. Eur. J. 2011, 17, 12596–12601; for
FeACTHNURGTNEUGN(NO3)3, see: e) S. Ma, J. Liu, S. Li, B. Chen, J.
Cheng, J. Kuang, Y. Liu, B. Wan, Y. Wang, J. Ye, Q.
Yu, W. Yuan, S. Yu, Adv. Synth. Catal. 2011, 353, 1005–
1017.
[23] For instance, see: a) T. Morihara, T. Chu, O. Ubeda, W.
Beech, G. M. Cole, J. Neurochem. 2002, 83, 1009–1012;
b) J. L. Eriksen, S. A. Sagi, T. E. Smith, S. Weggen, P.
Das, D. C. McLendon, V. V. Ozols, K. W. Jessing, K. H.
Zavitz, E. H. Koo, T. E. Golde, J. Clin. Invest. 2003,
112, 440–449.
[24] B. P. Babu, Y. Endo, J.-E. Bꢅckvall, Chem. Eur. J. 2012,
18, 11524–11527.
[25] A. Wells, M. Teria, T. Eve, Biochem. Soc. Trans. 2006,
34, 304–308.
[16] J. M. Hoover, S. S. Stahl, J. Am. Chem. Soc. 2011, 133,
16901–16910.
[17] a) J. Rodakiewicz-Nowak, S. M. Kasture, B. Dudek, J.
Haber, J. Mol. Catal. B: Enzym. 2000, 11, 1–11; b) F.
d’Acunzo, A. M. Barreca, C. Galli, J. Mol. Catal. B:
Enzym. 2004, 31, 25–30; c) L. Baratto, A. Candido, M.
Marzorati, F. Sagui, S. Riva, B. Danieli, J. Mol. Catal.
B: Enzym. 2006, 39, 3–8; d) S. Ncanana, L. Baratto, L.
Roncaglia, S. Riva, S. G. Burton, Adv. Synth. Catal.
2007, 349, 1507–1513.
[26] J. Srogl, S. Voltrova, Org. Lett. 2009, 11, 843–845.
[27] In these reactions we used 30 mol% of TEMPO in
order to push the reaction towards the formation of the
lactam derivatives. In fact, when compound 17 was
treated with 15 mol% of TEMPO and the laccase,
a conversion of 55% towards the hemiaminal was ob-
served.
[28] a) K. Kawada, T. Tsushima, Heterocycles 1989, 28, 573–
578; b) K. Seno, S. Hagishita, Chem. Pharm. Bull. 1989,
37, 948–954; c) S. Kamata, N. Haga, T. Tsuri, K.
Uchida, H. Kakushi, H. Arita, K. Hanasaki, J. Med.
Chem. 1990, 33, 229–239; d) M. Ohtani, M. Narisada, J.
Med. Chem. 1990, 33, 1027–1031; e) A. B. Holmes,
A. L. Smith, S. F. Williams, J. Org. Chem. 1991, 56,
1393–1405; f) C. G. Kokotos, V. K. Aggarwal, Chem.
Commun. 2006, 2156–2158.
[18] J. Rodakiewicz-Nowak, Top. Catal. 2000, 11–12, 419–
434.
[19] For more examples where different cosolvents have
been used in laccase-mediated reactions, see: a) A. M.
Barreca, M. Fabbrini, C. Galli, P. Gentili, S. Ljunggren,
J. Mol. Catal. B: Enzym. 2003, 26, 105–110; b) A. Intra,
S. Nicotra, S. Riva, B. Danieli, Adv. Synth. Catal. 2005,
347, 973–977; c) M. Zumꢁrraga, T. Bulter, S. Shleev, J.
Polaina, A. Martꢀnez-Arias, F. J. Plou, A. Ballesteros,
M. Alcalde, Chem. Biol. 2007, 14, 1052–1064; d) N. A.
Mohidem, H. B. Mat, Bioresour. Technol. 2012, 114,
472–477.
[20] For Cu/TEMPO examples: a) M. F. Semmelhack, C. R.
Schmid, D. A. Cortꢈs, C. S. Chou, J. Am. Chem. Soc.
1984, 106, 3374–3376; b) G. Ragagnin, B. Betzemeier,
S. Quici, P. Knochel, Tetrahedron 2002, 58, 3985–3991;
Adv. Synth. Catal. 0000, 000, 0 – 0
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