Cyclohexanone monooxygenase

Cyclohexanone monooxygenase
Identifiers
EC number 1.14.13.22
CAS number 52037-90-8
Databases
IntEnz IntEnz view
BRENDA BRENDA entry
ExPASy NiceZyme view
KEGG KEGG entry
MetaCyc metabolic pathway
PRIAM profile
PDB structures RCSB PDB PDBe PDBsum

Cyclohexanone monooxygenase (EC 1.14.13.22, cyclohexanone 1,2-monooxygenase, cyclohexanone oxygenase, cyclohexanone:NADPH:oxygen oxidoreductase (6-hydroxylating, 1,2-lactonizing)) is an enzyme with systematic name cyclohexanone,NADPH:oxygen oxidoreductase (lactone-forming).[1][2][3][4][5][6] This enzyme catalyses the following chemical reaction

cyclohexanone + NADPH + H+ + O2 \rightleftharpoons hexano-6-lactone + NADP+ + H2O

Cyclohexanone monooxygenase is a flavoprotein (FAD).

References

  1. ↑ Donoghue, N.A., Morris, D.B. and Trudgill, P.W. (1976). "The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB 9871". Eur. J. Biochem. 63 (1): 175–192. doi:10.1111/j.1432-1033.1976.tb10220.x. PMID 1261545.
  2. ↑ Sheng, D., Ballou, D.P. and Massey, V. (2001). "Mechanistic studies of cyclohexanone monooxygenase: chemical properties of intermediates involved in catalysis". Biochemistry 40 (37): 11156–11167. doi:10.1021/bi011153h. PMID 11551214.
  3. ↑ Stewart, J.D. (1998). "Cyclohexanone monooxygenase: a useful reagent for asymmetric Baeyer-Villiger reactions". Curr. Org. Chem. 2: 195–216.
  4. ↑ Chen, G., Kayser, M.M., Milhovilovic, M.D., Mrstik, M.E., Martinez, C.A. and Stewart, J.D. (1999). "Asymmetric oxidations at sulfur catalyzed by engineered strains that overexpress cyclohexanone monooxygenase". New J. Chem. 23 (8): 827–832. doi:10.1039/a902283j.
  5. ↑ Ottolina, G., Bianchi, S., Belloni, B., Carrea, G. and Danieli, B. (1999). "First asymmetric oxidation of tertiary amines by cyclohexanone monooxygenase". Tetrahedron Lett. 40 (48): 8483–8486. doi:10.1016/s0040-4039(99)01780-3.
  6. ↑ Colonna, S., Gaggero, N., Carrea, G., Ottolina, G., Pasta, P. and Zambianchi, F. (2002). "First asymmetric epoxidation catalysed by cyclohexanone monooxygenase". Tetrahedron Lett. 43 (10): 1797–1799. doi:10.1016/s0040-4039(02)00029-1.

External links

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