Citation: CHEN Ming, WANG Lin, TAN Tian, LUO Xue-Cai, ZHENG Zai, YIN Ruo-Chun, SU Ji-Hu, DU Jiang-Feng. Radical Mechanism of Laccase-Catalyzed Catechol Ring-Opening[J]. Acta Physico-Chimica Sinica, 2017, 33(3): 620-626. doi: 10.3866/PKU.WHXB201612011
漆酶催化邻苯二酚开环的自由基反应机制
English
Radical Mechanism of Laccase-Catalyzed Catechol Ring-Opening
-
-
[1]
Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev.1996, 96, 2563. doi: 10.1021/cr950046o
-
[2]
Solomon, E. I.; Heppner, D. E.; Johnston, E. M.; Ginsbach, J.W.; Cirera, J.; Qayyum, M.; Kieber-Emmons, M. T.; Kjaergaard, C. H.; Hadt, R. G.; Tian, L. Chem. Rev.2014, 114, 3659. doi: 10.1021/cr400327t
-
[3]
ten Have, R.; Teunissen, P. J. M. Chem. Rev.2001, 101, 3397. doi: 10.1021/cr000115l
-
[4]
Jiang, B.; Xu, X. Y.; Li, Z. Y. Chin. J. Org. Chem.2008, 28, 1715.[姜标, 徐向亚, 李祖义. 有机化学, 2008, 28, 1715.]
-
[5]
Lee, S. K.; George, S. D.; Antholine, W. E.; Hedman, B.; Hodgson, K. O.; Solomon, E. I. J. Am. Chem. Soc.2002, 124, 6180. doi: 10.1021/Ja0114052.
-
[6]
Hua, J. L.; Song, C. S.; Wang, G. H.; Cai, M. Z. Acta Phys.-Chim. Sin.1999, 15, 173.[花建丽, 宋才生, 王光辉, 蔡明中. 物理化学学报, 1999, 15, 173.] doi: 10.3866/PKU.WHXB19990215
-
[7]
Ma, G. X.; Zhong, Q. D.; Lu, T. H. Sci. China Chem.2010, 53, 1332. doi: 10.1007/s11426-010-3186-x
-
[8]
Zeng, H.; Liao, L.W.; Li, M. F.; Tao, Q.; Kang, J.; Chen, Y. X.Acta Phys.-Chim. Sin.2010, 26, 3217.[曾涵, 廖铃文, 李明芳, 陶骞, 康婧, 陈艳霞. 物理化学学报, 2010, 26, 3217.] doi: 10.3866/Pku.Whxb20101208
-
[9]
Zhang, Q.; Zhang, Y. Q.; Liu, X. Z.; Liang, Y. X.; Zhang, R. F.; Long, N. B. Chin. J. Inorg. Chem.2013, 29, 2065.[张群, 张育淇, 刘晓贞, 梁云霄, 张瑞丰, 龙能兵. 无机化学学报, 2013, 29, 2065.] doi: 10.3969/j.issn.1001-4861.2013.00.324
-
[10]
Li, Y.; Jiang, G. X.; Niu, J. F.; Wang, Y.; Hu, L. J. Prog. Chem.2009, 21, 2028.[李阳, 蒋国翔, 牛军峰, 王颖, 呼丽娟.化学进展, 2009, 21, 2028.]
-
[11]
Gupta, A.; Aartsma, T. J.; Canters, G.W. J. Am. Chem. Soc.2014, 136, 2707. doi: 10.1021/ja411078b
-
[12]
Drauz, K.; Gröger, H.; May, O. Enzyme Catalysis in Organic Synthesis, 3rd ed.; Drauz, K., Gröger, H., May, O. Eds.; Wiley-VCH:Weinheim, 2012.
-
[13]
Polaina, J.; MacCabe, A. P. Industrial Enzymes:Structure,Function, and Applications; Springer:Dordrecht, 2007.
-
[14]
Xu, F.; Damhus, T.; Danielsen, S.; Østergaard, L. H. CatalyticApplications of Laccase. In Modern Biooxidation, Wiley-VCHVerlag GmbH & Co. KGaA, 2007; pp 43-75.
-
[15]
Heppner, D. E.; Kjaergaard, C. H.; Solomon, E. I. J. Am. Chem.Soc.2013, 135, 12212. doi: 10.1021/ja4064525
-
[16]
Heppner, D. E.; Kjaergaard, C. H.; Solomon, E. I. J. Am. Chem.Soc.2014, 136, 17788. doi: 10.1021/ja509150j.
-
[17]
Wan, Y. Y.; Du, Y. M.; Miyakoshi, T. S. Sci. China Ser. B 2008, 51, 669. doi: 10.1007/s11426-008-0071-y
-
[18]
Rappoport, Z. The Chemistry of Phenols;Wiley:Hoboken, NJ, 2003.
-
[19]
Weinshilboum, R. M.; Otterness, D. M.; Szumlanski, C. L.Annu. Rev. Pharmacol. Toxicol 1999, 39, 19. doi: 10.1146/annurev.pharmtox.39.1.19
-
[20]
Brown, C. K.; Vetting, M.W.; Earhart, C. A.; Ohlendorf, D. H.Annu. Rev. Microbiol.2004, 58, 555. doi: 10.1146/annurev.micro.57.030502.090927
-
[21]
Kovaleva, E. G.; Lipscomb, J. D. Science 2007, 316, 453. doi: 10.1126/science.1134697
-
[22]
Zard, S. Z. Advances in Free Radical Chemistry, Vol. 2; JaiPress:Stamford, Conn., 1999.
-
[23]
Chatgilialoglu, C.; Studer, A. Encyclopedia of Radicals in Chemistry, Biology and Materials;Wiley-Blackwell:Oxford, 2012.
-
[24]
Gerson, F.; Huber, W. Electron Spin Resonance Spectroscopy of Organic Radicals;Wiley-VCH:Weinheim, Great Britain, 2003.
-
[25]
Buettner, G. R. Free Radic Biol. Med.1987, 3, 259. doi: 10.1016/S0891-5849(87)80033-3
-
[26]
Alberti, A.; Macciantelli, D. Spin Trapping. In Electron Paramagnetic Resonance, JohnWiley & Sons, Inc.:Hoboken, New Jersey, 2008; pp 285-324.
-
[27]
Sanvoisin, J.; Langley, G. J.; Bugg, T. D. H. J. Am. Chem. Soc.1995, 117, 7836. doi: 10.1021/Ja00134a041
-
[28]
Spence, E. L.; Langley, G. J.; Bugg, T. D. H. J. Am. Chem. Soc.1996, 118, 8336. doi: 10.1021/ja9607704
-
[29]
Lin, G.; Reid, G.; Bugg, T. D. H. J. Am. Chem. Soc.2001, 123, 5030. doi: 10.1021/ja004280u
-
[30]
Xin, M.; Bugg, T. D. H. J. Am. Chem. Soc.2008, 130, 10422. doi: 10.1021/ja8029569
-
[31]
Brivio, M.; Schlosrich, J.; Ahmad, M.; Tolond, C.; Bugg, T. D.H. Org. Biomol. Chem.2009, 7, 1368. doi: 10.1039/b821559f
-
[32]
Mander, L. N.; Williams, C. M. Tetrahedron 2003, 59, 1105. doi: 10.1016/S0040-4020(02)01492-8
-
[33]
Spirkova, K.; Kada, R. Chem. Pap.1987, 41, 787.
-
[34]
Babij, N. R.; McCusker, E. O.; Whiteker, G. T.; Canturk, B.; Choy, N.; Creemer, L. C.; De Amicis, C. V.; Hewlett, N. M.; Johnson, P. L.; Knobelsdorf, J. A.; Li, F. Z.; Lorsbach, B. A.; Nugent, B. M.; Ryan, S. J.; Smith, M. R.; Yang, Q. Org.Process. Res. Dev.2016, 20, 661. doi: 10.1021/acs.oprd.5b00417
-
[35]
Fulmer, G. R.; Miller, A. J. M.; Sherden, N. H.; Gottlieb, H. E.; Nudelman, A.; Stoltz, B. M.; Bercaw, J. E.; Goldberg, K. I.Organometallics 2010, 29, 2176. doi: 10.1021/om100106e
-
[36]
Gunther, H. A. Nmr Spectroscopy:Basic Principles, Concepts and Applications in Chemistry, 3rd ed.; completely revised andupdated edition.
-
[37]
Pietruszka, J.; Wang, C. Green Chemistry 2012, 14, 2402. doi: 10.1039/C2GC35662G
-
[38]
Abdel-Mohsen, H. T.; Conrad, J.; Beifuss, U. J. Org. Chem.2013, 78, 7986. doi: 10.1021/jo401193e
-
[39]
Su, Y. J.; Jia, W.; Jiao, N. Synthesis-Stuttgart 2011, 1678. doi: 10.1055/s-0030-1260028
-
[1]
-
扫一扫看文章
计量
- PDF下载量: 9
- 文章访问数: 1522
- HTML全文浏览量: 286

下载: