Product identification of guaiacol oxidation catalyzed by manganese peroxidase

Sangpill Hwang; Chang-Ha Lee; Ik-Sung Ahn

Journal of Industrial and Engineering Chemistry, Vol.14, No.4, 487-492, July, 2008

DOI10.1016/j.jiec.2008.02.008 Export Citation

Product identification of guaiacol oxidation catalyzed by manganese peroxidase

Sangpill Hwang, Chang-Ha Lee , and Ik-Sung Ahn^†

Department of Chemical Engineering, Yonsei University, Seoul 120-749, Republic of Korea

E-mail:

The mechanism underlying the oxidation of guaiacol (2-methoxyphenol) by manganese peroxidase (MnP) was studied by structural identification of the products. After separation by TLC, the products were characterized by NMR, GC.MS, and LC.MS. They were determined to be 3,30-dimethoxy-4,40-biphenol, a mixture of 3,30-dimethoxy-4,40-biphenoquinone and 3,50-dimethoxy-4,40-biphenoquinone, 6-methoxy-4-(4- hydroxy-3-methoxyphenyl)-1,2-benzoquinone, 3-(4-hydroxy-3-methoxy-phenyl)-5,30-dimethoxy-4,40-biphenol, and a mixture of 5-(4-hydroxy-3-methoxyphenyl)-3,30-dimethoxy-4,40-biphenoquinone and 3-(4-hydroxy-3-methoxyphenyl)-5,30-dimethoxy-4,40-biphenoquinone. From the direct GC.MS analysis, two other products were identified as 3-methoxy-catechol and 2-methoxy-1,4-benzoquinone. The reaction mechanism of MnP-catalyzed guaiacol oxidation is suggested on the basis of the structural information obtained for these products.

Keywords:Oxidation;Guaiacol;Manganese peroxidase;Radical coupling;Structural identification

[References]

Kuwahara M, Glenn JK, Morgan MA, Gold MH, Febs Lett., 169, 247 (1984)
Glenn JK, Gold MH, Arch. Biochem. Biophys., 242, 329 (1985)
Paszcynski A, Huynh VB, Crawford R, FEMS Microbiol. Lett., 29, 37 (1985)
Kersten PJ, Tien M, Kalyanamaran B, Kirk TK, J. Biol. Chem., 260, 2609 (1985)
Wariishi H, Valli K, Gold MH, Biochemistry, 28, 6017 (1989)
Tuor U, Wariishi H, Schoemaker HE, Gold MH, Biochemistry, 31, 4986 (1992)
Wariishi H, Dunford HB, MacDonald ID, Gold MH, J. Biol. Chem., 264, 3335 (1989)
Wariishi H, Valli K, Gold MH, J. Biol. Chem., 267, 23688 (1992)
Lackner R, Srebotnik E, Messner K, Biochem. Biophys. Res. Commun., 178, 1092 (1991)
Glenn JK, Akileswaran L, Gold MH, Arch. Biochem. Biophys., 251, 688 (1986)
Forrester IT, Grabski AC, Burgess RR, Leatham GF, Biochem. Biophys. Res. Commun., 157, 992 (1988)
Doerge DR, Divi RL, Churchwell MI, Anal. Biochem., 250, 10 (1997)
Taurog A, Dorris Jr. ML, Guziec FS, Anal. Biochem., 205, 271 (1992)
Tonami H, Uyama H, Nagahata R, Kobayashi S, Chem. Lett., 33(7), 796 (2004)
Park SY, Jun K, J. Ind. Eng. Chem., 13(1), 105 (2007)
Chung E, Oh J, Hwang S, Ahn IS, Yoon YJ, Biotechnol. Lett., 27(7), 477 (2005)
Bonnarme P, Delattre M, Corrieu G, Asther M, Enzyme Microb. Technol., 13, 727 (1991)
Paszczynski A, Crawford R, Huynh VB, Methods Enzymol., 161, 264 (1988)
Kobayashi A, Koguchi Y, Kanzaki H, Kajiyama SI, Biosci. Biotechnol. Biochem., 58, 133 (1994)
Simmons KE, Minard RD, Bollag JM, Soil Sci. Soc. Am. J., 52, 1356 (1988)
Crawford RL, Robinson LE, Foster RD, Appl. Environ. Microbiol., 41, 1112 (1981)

[Referenced By]

[Related Articles]

[1] Kuwahara M, Glenn JK, Morgan MA, Gold MH, Febs Lett., 169, 247 (1984)

[2] Glenn JK, Gold MH, Arch. Biochem. Biophys., 242, 329 (1985)

[3] Paszcynski A, Huynh VB, Crawford R, FEMS Microbiol. Lett., 29, 37 (1985)

[4] Kersten PJ, Tien M, Kalyanamaran B, Kirk TK, J. Biol. Chem., 260, 2609 (1985)

[5] Wariishi H, Valli K, Gold MH, Biochemistry, 28, 6017 (1989)

[6] Tuor U, Wariishi H, Schoemaker HE, Gold MH, Biochemistry, 31, 4986 (1992)

[7] Wariishi H, Dunford HB, MacDonald ID, Gold MH, J. Biol. Chem., 264, 3335 (1989)

[8] Wariishi H, Valli K, Gold MH, J. Biol. Chem., 267, 23688 (1992)

[9] Lackner R, Srebotnik E, Messner K, Biochem. Biophys. Res. Commun., 178, 1092 (1991)

[10] Glenn JK, Akileswaran L, Gold MH, Arch. Biochem. Biophys., 251, 688 (1986)

[11] Forrester IT, Grabski AC, Burgess RR, Leatham GF, Biochem. Biophys. Res. Commun., 157, 992 (1988)

[12] Doerge DR, Divi RL, Churchwell MI, Anal. Biochem., 250, 10 (1997)

[13] Taurog A, Dorris Jr. ML, Guziec FS, Anal. Biochem., 205, 271 (1992)

[14] Tonami H, Uyama H, Nagahata R, Kobayashi S, Chem. Lett., 33(7), 796 (2004)

[15] Park SY, Jun K, J. Ind. Eng. Chem., 13(1), 105 (2007)

[16] Chung E, Oh J, Hwang S, Ahn IS, Yoon YJ, Biotechnol. Lett., 27(7), 477 (2005)

[17] Bonnarme P, Delattre M, Corrieu G, Asther M, Enzyme Microb. Technol., 13, 727 (1991)

[18] Paszczynski A, Crawford R, Huynh VB, Methods Enzymol., 161, 264 (1988)

[19] Kobayashi A, Koguchi Y, Kanzaki H, Kajiyama SI, Biosci. Biotechnol. Biochem., 58, 133 (1994)

[20] Simmons KE, Minard RD, Bollag JM, Soil Sci. Soc. Am. J., 52, 1356 (1988)

[21] Crawford RL, Robinson LE, Foster RD, Appl. Environ. Microbiol., 41, 1112 (1981)