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Tetrahydroberberine oxidase

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tetrahydroberberine oxidase
Identifiers
EC no. 1.3.3.8
CAS no. 114705-00-9
Databases
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BRENDA BRENDA entry
ExPASy NiceZyme view
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MetaCyc metabolic pathway
PRIAM profile
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Gene Ontology AmiGO / QuickGO
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NCBI proteins

(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. [3]

+ H+
 
 
2 O2
2 H2O2
Tetrahydroberberine oxidase
 
 
 

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. [4] [5]

Other quaternary benzylisoquinoline alkaloids can be produced by this enzyme, provided that their precursor has (S} configuration at the centre next to the nitrogen. For example, (S)-isocorypalmine is oxidised to columbamine; tetrahydropalmatine to palmatine, and tetrahydropapaverine to papaverine. [3] [6]

+ H+
 
 
2 O2
2 H2O2
Tetrahydroberberine oxidase
 
 
 


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. 1 2 Enzyme 1.3.3.8 at KEGG Pathway Database.
  4. 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. Bibcode:1988PChem..27..979O. doi:10.1016/0031-9422(88)80255-3.
  5. 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.
  6. Mascavage, Linda M.; Jasmin, Serge; Sonnet, Philip E.; Wilson, Michael; Dalton, David R. (2010). "Alkaloids". Ullmann's Encyclopedia of Industrial Chemistry. p. 54. doi:10.1002/14356007.a01_353.pub2. ISBN   978-3-527-30385-4.


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