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Tetrahydroberberine oxidase

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tetrahydroberberine oxidase
Identifiers
EC number1.3.3.8
CAS number114705-00-9
Databases
IntEnzIntEnz view
BRENDABRENDA entry
ExPASyNiceZyme view
KEGGKEGG entry
MetaCycmetabolic pathway
PRIAMprofile
PDB structuresRCSB PDB PDBe PDBsum
Gene OntologyAmiGO / QuickGO

(S)-Tetrahydroberberine oxidase (EC 1.3.3.8) is an enzyme that catalyzes the final transformation in the biosynthesis of berberine, a quaternary benzylisoquinoline alkaloid of the protoberberine structural subgroup.[1][2] This reaction pathway catalyzes the four-electron oxidation of (S)-tetrahydroberberine (also known as (S)-canadine) in the presence of oxygen to produce berberine and hydrogen peroxide as products.

(S)-Tetrahydroberberine + 2 O2  ⇌  Berberine + 2 H2O2

This enzyme belongs to the family known as oxidoreductases, in this instance the CH-CH moiety acts as the electron donor with oxygen acting as the electron acceptor. The systematic name of this enzyme is (S)-tetrahydroberberine:oxygen oxidoreductase; but it is also known as (S)-THB oxidase, tetrahydroberberine oxidase, and decreasingly, as (S)-tetrahydroprotoberberine oxidase.[3][4]

References

  1. ^ Amann M, Nagakura N, Zenk MH (July 1988). "Purification and properties of (S)-tetrahydroprotoberberine oxidase from suspension-cultured cells of Berberis wilsoniae". European Journal of Biochemistry. 175 (1): 17–25. doi:10.1111/j.1432-1033.1988.tb14160.x. PMID 3402447.
  2. ^ Amann M, Nagakura N, Zenk MH (1984). "(S)-tetrahydroprotoberberine oxidase the final enzyme in protoberberine biosynthesis". Tetrahedron Lett. 25 (9): 953–4. doi:10.1016/S0040-4039(01)80071-X.
  3. ^ Okada N, Shinmyo A, Okada H, Yamada Y (1988). "Purification and characterization of (S)-tetrahydroberberine oxidase from cultured Coptis japonica cells". Phytochemistry. 27 (4): 979–82. doi:10.1016/0031-9422(88)80255-3.
  4. ^ Okada N, Koizumi N, Tanaka T, Ohkubo H, Nakanishi S, Yamada Y (January 1989). "Isolation, sequence, and bacterial expression of a cDNA for (S)-tetrahydroberberine oxidase from cultured berberine-producing Coptis japonica cells". Proceedings of the National Academy of Sciences of the United States of America. 86 (2): 534–8. Bibcode:1989PNAS...86..534O. doi:10.1073/pnas.86.2.534. PMC 286506. PMID 2463630.


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Tetrahydroberberine oxidase
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