Preparation and evaluation of the oxidation ability of hematin-appended 6-amino-6-deoxycellulose

Journal of Wood Chemistry and Technology

Volumn 34, Issue 4, 2014, Pages 262-272

  Ozawa, Maki ^a   Fukutome, Asuka ^a   Sannami, Yumi ^a   Kamitakahara, Hiroshi ^a   Takano, Toshiyuki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Biomimetic catalyst; Cellulose derivative ferriprotoporphyrin; Porphyrin; Sinapyl alcohol

Indexed keywords

CATALYTIC OXIDATION; PORPHYRINS;

1 ,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE; ASYMMETRIC INDUCTION; BIOMIMETIC CATALYSTS; CARBONYLDIIMIDAZOLE; HORSE-RADISH PEROXIDASE; N ,N-DIMETHYLFORMAMIDE; OXIDATION ACTIVITIES; SINAPYL ALCOHOLS;

OXIDATION;

EID: 84896329891     PISSN: 02773813     EISSN: 15322319     Source Type: Journal    
DOI: 10.1080/02773813.2013.869605     Document Type: Article

References (18)

1. Redl, F.X.; Lutz, M.; Daub, J. Chemistry of porphyrin-appended cellulose strands with a helical structure: Spectroscopy, electrochemistry, and in situ circular dichroism spectroelectrochemistry. Chemical European Journal 2001, 7, 5350-5358.
2. Dias, S.L.P.; Gushikem, Y.; Ribeiro, E.S.; Benvenutti, E.V. Cobalt(II) hematoporphyrin IX and protoporphyrin IX complexes immobilized on highly dispersed titanium(IV) oxide on a cellulose microfiber surface: Electrochemical properties and dissolved oxygen reduction study. Journal of Electroanalytical Chemistry 2002, 523, 64-69.
3. Sakakibara, K.; Ogawa, Y.; Nakatsubo, F. First cellulose Langmuir-Blodgett films towards photocurrent generation systems. Macromolecular Rapid Communications 2007, 28, 1270-1275.
4. Boufi, S.; Vilar, M.R.; Parra, V.; Ferraria, A.M.; Botelho do Rego, A.M. Grafting porphyrins on cellulose nanometric films. Langmuir 2008, 24, 7309-7315.
5. Akkara, J.A.;Wang, J.; Yang, D.-P.; Gonsalves, K. Hematin-catalyzed polymerization of phenol compounds. Macromolecules 2000, 33, 2377-2382.
6. Sakai, S.; Moriyama, K.; Taguchi, K.; Kawakami, K. Hematin is an alternative catalyst to horseradish peroxidase for in situ hydrogenation of polymers with phenolic hydroxyl groups in vivo. Biomacromolecules 2010, 11, 2179-2183.
7. Singh, A.; Roy, S.; Samuelson, L.; Bruno, F.; Nakarajan, R.; Kumar, J.; John, V.; Kaplan, D.L. Peroxidase, hematin and peglated-hematin catalyzed vinyl polymerizations in water. Journal of Macromolecular Science - Pure Applied Chemistry 2001, A38(12), 1219-1230.
8. Nagarajan, A.; Nagarajan, R.; Bruno, F.; Samuelson, L.A.; Kumar, J. A stable biomimetic redox catalyst obtained by the enzyme catalyzed amidation of iron porphyrin. Green Chemistry 2009, 11, 334-338.
9. Maux, P.L.; Simonneaux, G. First enantioselective iron-porphyrin- catalyzed sulfide oxidation with aqueous hydrogen peroxide. Chem. Commun. 2011, 47, 6957-6959.
10. Olsen, K.W. Affinity chromatography of heme-binding proteins: Synthesis and characterization of hematin-and hematoporphyrin-agarose. In: Methods in Enzymology: Vol. 123, Vitamins and Coenzymes Part H; Chytil, F.; McCormick, D.B., Eds.; Academic Press: Orlando, FL, USA, 1986, 324-331.
11. Matsui, Y.; Ishikawa J.; Kamitakahara, H.; Takano, T.; Nakatsubo, F. Facile synthesis of 6-amino-6-deoxycellulose. Carbohydrate Research 2005, 340, 1403-1406.
12. Yamaguchi, H.; Nakatsubo, F.; Katsura, Y.; Murakami, K. Characterization of (+)-and (-)-syringaresinol di-?-D-glucosides. Holzforschung 1990, 44, 381-385.
13. Klemm, D.; Philipp, B.; Heinze, T.; Heinze, U.; Wagenknecht, W. Comprehensive Cellulose Chemistry; Wiley-VCH: Weinheim, Germany, 1998.
14. Melki, P.G. Résultats obtenus en spectrographie infrarouge sur quelques porphyrines entre 4000 et 400 cm-1. Biochimie. 1971, 53, 875-885.
15. Ambroshio, K.; Rueda, E.; Ferreira, M.L. Magnetite-supported hematin as a biomimetic of horseradish peroxidase in phenol removal by polymerization. Biocatalysis and Biotransformation 2004, 22, 35-44.
16. Tonami, H.; Uyama, H.; Nagahata, R.; Kobayashi, S. Guaiacol oxidation products in the enzymeactivity assay reaction by horseradish peroxidase catalysis. Chemistry Letters 2004, 33, 796-797.
17. Crespo M.P.; Tilley, L.; Klonis, N. Solution behavior of hematin under acidic conditions and implications for its interactions with chloroquine. J. Biol. Inorg. Chem. 2010, 15, 1009-1022.
18. Tanahashi, M.; Higuchi, T. Effect of the hydrophobic regions of hemicelluloses on dehydrogenative polymerization of sinapyl alcohol. Mokuzai Gakkaishi 1990, 36, 424-428.