18O incorporation from H2 18O2 in the oxidation of N-methylcarbazole and sulfides catalyzed by microperoxidase-11

Shigeo Nakamura, Tadahiko Mashino, Masaaki Hirobe

研究成果: Article

34 引用 (Scopus)

抄録

Microperoxidase-11 (MP-11), prepared by pepsin digestion of cytochrome c, contains protoheme IX and one proximal histidine ligand. MP-11 oxygenated N-methylcarbazole, methyl phenyl sulfide, and phenacyl phenyl sulfide with 80%, 100%, and 96% 18O atom incorporation from H2 18O2, respectively. These results indicate that the oxygen atom on heme iron of MP-11 immediately rebinds to one-electron-oxidized intermediates of the substrates and that MP-11 catalyzes N-demethylation through a cytochrome P-450-like mechanism rather than a peroxidase-like mechanism.

元の言語English
ページ(範囲)5409-5412
ページ数4
ジャーナルTetrahedron Letters
33
発行部数37
DOI
出版物ステータスPublished - 1992 9 8
外部発表Yes

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Sulfides
Oxidation
Heme
Atoms
Pepsin A
Cytochromes c
Histidine
Cytochrome P-450 Enzyme System
Peroxidase
Digestion
Iron
Electrons
Oxygen
Ligands
N-methylcarbazole
microperoxidase
Substrates

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

これを引用

18O incorporation from H2 18O2 in the oxidation of N-methylcarbazole and sulfides catalyzed by microperoxidase-11. / Nakamura, Shigeo; Mashino, Tadahiko; Hirobe, Masaaki.

:: Tetrahedron Letters, 巻 33, 番号 37, 08.09.1992, p. 5409-5412.

研究成果: Article

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abstract = "Microperoxidase-11 (MP-11), prepared by pepsin digestion of cytochrome c, contains protoheme IX and one proximal histidine ligand. MP-11 oxygenated N-methylcarbazole, methyl phenyl sulfide, and phenacyl phenyl sulfide with 80{\%}, 100{\%}, and 96{\%} 18O atom incorporation from H2 18O2, respectively. These results indicate that the oxygen atom on heme iron of MP-11 immediately rebinds to one-electron-oxidized intermediates of the substrates and that MP-11 catalyzes N-demethylation through a cytochrome P-450-like mechanism rather than a peroxidase-like mechanism.",
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AU - Hirobe, Masaaki

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AB - Microperoxidase-11 (MP-11), prepared by pepsin digestion of cytochrome c, contains protoheme IX and one proximal histidine ligand. MP-11 oxygenated N-methylcarbazole, methyl phenyl sulfide, and phenacyl phenyl sulfide with 80%, 100%, and 96% 18O atom incorporation from H2 18O2, respectively. These results indicate that the oxygen atom on heme iron of MP-11 immediately rebinds to one-electron-oxidized intermediates of the substrates and that MP-11 catalyzes N-demethylation through a cytochrome P-450-like mechanism rather than a peroxidase-like mechanism.

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