Full Paper

You have free access to this content

A Novel Synthesis of Bioactive Catechols by Layer-by-Layer Immobilized Tyrosinase in an Organic Solvent Medium

Dr. Melissa Guazzaroni,
Dr. Marina Pasqualini,
Dr. Giorgia Botta,
Prof. Raffaele Saladino^*

Article first published online: 21 OCT 2011

DOI: 10.1002/cctc.201100229

Issue

ChemCatChem

Volume 4, Issue 1, pages 89–99, January 2, 2012

Additional Information

How to Cite

Guazzaroni, M., Pasqualini, M., Botta, G. and Saladino, R. (2012), A Novel Synthesis of Bioactive Catechols by Layer-by-Layer Immobilized Tyrosinase in an Organic Solvent Medium. ChemCatChem, 4: 89–99. doi: 10.1002/cctc.201100229

Author Information

Department of Agrobiology and Agrochemistry, University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo (Italy), Fax: (+39) 0761-357242

Email: Prof. Raffaele Saladino (saladino@unitus.it)

^*Department of Agrobiology and Agrochemistry, University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo (Italy), Fax: (+39) 0761-357242

Publication History

Issue published online: 27 DEC 2011
Article first published online: 21 OCT 2011
Manuscript Received: 11 JUL 2011

Funded by

Italian Miur PRIN 2008

ARTICLE TOOLS

View Full Article (HTML) Get PDF (753K)

1
H. W. Duchworth, J. E. Coleman, J. Biol. Chem. 1970, 245, 1613–1625.
- PubMed,
- Web of Science® Times Cited: 351
2
2a
S. Halaouli, M. Asther, J. C. Sigoillot, M. Hamdi, A. Lomascolo, J. Appl. Microbiol. 2006, 100, 219–232;
Direct Link:
2b
S.-Y. Seo, V. K. Sharma, N. Sharma, J. Agric. Food Chem. 2003, 51, 2837–2853.
3
3a
L. T. Zheng, G. M. Ryu, B. M. Kwon, W. H. Lee, K. Suk, Eur. J. Pharmacol. 2008, 588, 106–113;
3b
L. C. Nolan, K. E. O’Connor, Biotechnol. Lett. 2008, 30, 1879–1891;
3c
T. Shimizu, Y. Nakanishi, M. Nakahara, N. Wada, Y. Moro-Oka, T. Hirano, T. Konishi, S. Matsugo, J. Clin. Biochem. Nutr. 2010, 47, 181–190.
- CrossRef,
- PubMed,
- CAS,
- Web of Science®
4
4a
M. E. Marín-Zamora, F. Rojas-Melgarejo, F. García-Cánovas, P. A. García-Ruiz, J. Biotechnol. 2009, 139, 163–168;
4b
G. M. J. Carvalho, T. L. M. Alves, D. M. G. Freire, Appl. Biochem. Biotechnol. 2000, 84, 791–800;
4c
R. Ullrich, M. Hofrichter, Cell. Mol. Life Sci. 2007, 64, 271–293;
4d
R. Octávio de Faria, V. Rotuno-Moure, M. A. Lopes deAlmeida, N. Krieger, D. A. Mitchell, Food Technol. Biotechnol. 2007, 45, 287–294.
5
P. Estrada, R. Sanchez-Muniz, C. Acebal, R. Arche, M. P. Castillon, Biotechnol. Appl. Biochem. 1991, 14, 12–20.
- CAS
6
J. C. Espín, C. Soler-Rivas, E. Cantos, F. A. Tomás-Barberán, H. J. Wichers, J. Agric. Food Chem. 2001, 49, 1187–1193.
7
R. Kazandjiand, A. M. Klibanov, J. Am. Chem. Soc. 1985, 107, 5448–5450.
- CrossRef,
- Web of Science® Times Cited: 206
8
8a
S. Kermasha, H. Bao, B. Bisakowski, V. Yaylayan, J. Mol. Catal. B 2002, 19, 335–345;
- CrossRef,
- Web of Science® Times Cited: 2
8b
S. Kermasha, H. Bao, B. Bisakowski, J. Mol. Catal. B 2001, 11, 929–938;
8c
S. Kermasha, M. Tse, J. Chem. Technol. Biotechnol. 2000, 75, 475–483.
Direct Link:
9
N. Durán, M. A. Rosa, A. D′Annibale, L. Gianfreda, Enzyme Microb. Technol. 2002, 31, 907–931.
- CrossRef,
- Web of Science® Times Cited: 245
10
10a
J. C. Warrington, B. A. Saville, Biotechnol. Bioeng. 1999, 65, 325–333;
Direct Link:
10b
P. Estrada, W. Baroto, M. P. Castillon, C. Acebal, R. Arche, J. Chem. Technol. Biotechnol. 1993, 56, 59–65.
Direct Link:
11
11a
P. Ilabahen, L. Roland, M. Kitti, H. Dietmar, R. Thomas, P. Antje, Holzforschung 2009, 63, 715–720;
11b
M. E. Russo, P. Giardina, A. Marzocchella, P. Salatino, G. Sannia, Enzyme Microb. Technol. 2008, 42, 521–530;
11c
L. Baratto, A. Candido, M. Marzorati, F. Sagui, S. Riva, B. Danieli, J. Mol. Catal. B 2006, 39, 3–8.
12
12a
D. Mislovičová, J. Turjan, A. Vikartovská, V. Pätoprstý, J. Mol. Catal. B 2009, 60, 45–49;
12b
D. Mislovičová, E. Michálková, A. Vikartovská, Process Biochem. 2007, 42, 704–709.
13
P. Sukyai, T. Rezìc, C. Lorenz, K. Mueangtoom, W. Lorenz, D. Haltrich, R. Ludwig, J. Biotechnol. 2008, 135, 281–290.
14
G. Decher, Science 1997, 277, 1232–1237.
15
G. Decher, J. Schmitt, Prog. Colloid Polym. Sci. 1992, 89, 160–164.
- CrossRef,
- CAS
16
C. Held, A. Kandelbauer, M. Schroeder, A. Cavaco-Paulo, G. M. Gubitz, Environ. Chem. Lett. 2005, 3, 74–77.
17
17a
S. Bouchilloux, P. McMahill, H. S. Mason, J. Biol. Chem. 1963, 238, 1699–1707;
17b
B. Marongiu, A. Piras, S. Porcedda, E. Tuveri, E. Sanjust, M. Meli, F. Sollai, P. Zucca, A. Rescigno, J. Agric. Food Chem. 2007, 55, 10022–10027.
18
Y. Masamoto, S. Iida, M. Kubo, Planta Med. 1980, 40, 361–365.
19
B. S. Wolfenden, R. L. Willson, J. Chem. Soc. Perkin Trans. 2 1982, 805–810.
20
H. Lineweaver, D. Burk, J. Am. Chem. Soc. 1934, 56, 658–666.
- CrossRef,
- CAS
21
21a
P. Rauch, E. N. Ferri, S. Girotti, H. Rauchova, G. Carrea, R. Bovara, F. Fini, A. Roda, Anal. Biochem. 1997, 245, 133–140;
21b
E. Katchalski-Katzir, D. M. Kraemer, J. Mol. Catal. B 2000, 10, 157–176.
22
22a
C. Acharya, V. Kumar, R. Sen, S. C. Kundu, Biotechnol. J. 2008, 3, 226–233;
Direct Link:
22b
A. Arslan, S. Kiralp, L. Toppare, Y. Yagci, Int. J. Biol. Macromol. 2005, 35, 163–167;
22c
C. L. Huang, W. C. Cheng, J. C. Yang, M. C. Chi, J. H. Chen, H. P. Lin, L. L. Lin, J. Ind. Microbiol. Biotechnol. 2010, 37, 717–725.
- CrossRef,
- PubMed,
- CAS,
- Web of Science®
23
H. Frauenfelder, P. W. Fenimore, B. H. McMahon, Biophys. Chem. 2002, 98, 35–48.
24
Y. Pocker, Cell. Mol. Life Sci. 2000, 57, 1008–1017.
25
Y. Levy, J. N. Onuchic, Annu. Rev. Biophys. Biomol. Struct. 2006, 35, 389–415.
26
D. Zhong, Adv. Chem. Phys. 2009, 143, 83–149.
27
27a
S. Tuncagil, S. K. Kayahan, G. Bayramoglu, M. Y. Arica, L. Toppare, J. Mol. Catal. B 2009, 58, 187–193;
27b
M. Puri, H. Kaur, J. F. Kennedy, J. Chem. Technol. Biotechnol. 2005, 80, 1160–1165;
Direct Link:
27c
D. Quan, Y. Kim, W. Shin, J. Electroanal. Chem. 2004, 561, 181–189.
28
S. G. Burton, J. R. Duncan, P. T. Kaye, P. D. Rose, Biotechnol. Bioeng. 1993, 42, 938–944.
Direct Link:
29
G. K. Ziyatdinova, A. A. Gainetdinova, G. K. Budnikov, J. Anal. Chem. 2010, 65, 929–934.
30
C. R. Dawson, W. B. Tarpley, Ann. N. Y. Acad. Sci. 1963, 100, 937–950.
- PubMed,
- CAS,
- ADS
31
Z-P. Xiao, T-W. Ma, W-C. Fu, X-C. Peng, A-H. Zhang, H-L Zhu, Eur. J. Med. Chem. 2010, 45, 5064–5070.
32
R. Costia, R. Di Santoa, M. Artico, S. Massa, R. Ragno, R. Loddo, M. La Colla, E. Tramontano, P. La Colla, A. Pani, Bioorg. Med. Chem. 2004, 12, 199–215.
33
H. T. Balaydın, İ. Gülçin, A. Menzek, S. Göksu, E. Şahin, J. Enzyme Inhib. Med. Chem. 2010, 25, 685–695.
34
M. Colon, P. Guevara, W. H. Gerwick, J. Nat. Prod. 1987, 50, 368–374.
35
G. Sukhorukov, A. Fery, H. Möhwald, Prog. Polym. Sci. 2005, 30, 885–897.
36
C. Y. Gao, E. Donath, H. Möhwald, J. Shen, Angew. Chem. 2002, 114, 3943–3947;
Direct Link:
Angew. Chem. Int. Ed. 2002, 41, 3789–3793.
Direct Link:
37
37a
M. Tudorache, D. Mahalu, C. Teodorescu, R. Stan, C. Bala, V. I. Parvulescu, J. Mol. Catal. B 2011, 69, 133–139;
37b
D. M. Dotzauer, A. Abusaloua, S. Miachon, J.-A. Dalmon, M. L. Bruening, Appl. Catal. B 2009, 91, 180–188.
38
S. Shinkai, Y. Kusano, O. Manabe, J. Chem. Soc. Perkin Trans. 1 1980, 1622–5.
39
C. Mateo, O. Abian, G. Fernandez-Lorente, J. Predoche, R. Fernandez-Lafuente, J. M. Guisan, Biotechnol. Prog. 2002, 18, 629–634.
Direct Link:
40
40a
R. Perazzini, R. Saladino, M. Guazzaroni, C. Crestini, Bioorg. Med. Chem. 2011, 19, 440–447;
40b
O. P. Tiourina, A. A. Antipov, G. B. Sukhorukov, N. I. Larionova, Y. Lvov, H. Möhwald, Macromol. Biosci. 2001, 1, 209–214.
Direct Link:
- Abstract
- PDF(117K)
41
41a
J. J. Sedmak, S. E. Grossberg, Anal. Biochem. 1977, 79, 544–552;
41b
M. M. Bradford, Anal. Biochem. 1976, 72, 248–254.
42
42a
J. N. Rodríguez-López, L. Gómez-Fenoll, M. J. Penalver, P. A. García-Ruíz, V. Varón, F. Martínez-Ortíz, F. García-Cánovas, J. Tudela, Biochim. Biophys. Acta Protein Struct. Mol. Enzymol. 2001, 1548, 238–256;
42b
C. C. Sweeley, R. Bentlry, M. Makita, W. W. Wells, J. Am. Chem. Soc. 1963, 85, 2497–2507.
43
N. Chernyak, A. S. Dudnik, C. Huang, V. Gevorgyan, J. Am. Chem. Soc. 2010, 132, 8270–8272.
44
O. Chantarasriwong, W. C. Cho, A. Batova, W. Chavasiri, C. Moore, A. L. Rheingold, E. A. Theodorakis, Org. Biomol. Chem. 2009, 7, 4886–4894.
45
S. Nakayama, F. Ikeda, US Patent 5102906, 4985458, 1988.

View Full Article (HTML) Get PDF (753K)

JOURNAL TOOLS

JOURNAL MENU

FIND ISSUES

FIND ARTICLES

GET ACCESS

FOR CONTRIBUTORS

ABOUT THIS JOURNAL

SPECIAL FEATURES

A Novel Synthesis of Bioactive Catechols by Layer-by-Layer Immobilized Tyrosinase in an Organic Solvent Medium

ChemCatChem

How to Cite

Author Information

Publication History

Funded by

ARTICLE TOOLS

More content like this

JOURNAL TOOLS

JOURNAL MENU

FIND ISSUES

FIND ARTICLES

GET ACCESS

FOR CONTRIBUTORS

ABOUT THIS JOURNAL

SPECIAL FEATURES

A Novel Synthesis of Bioactive Catechols by Layer-by-Layer Immobilized Tyrosinase in an Organic Solvent Medium

ChemCatChem

How to Cite

Author Information

Publication History

Funded by

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

More content like this