KEGG   ENZYME: 1.14.14.124
Entry
EC 1.14.14.124              Enzyme                                 
Name
dihydromonacolin L hydroxylase;
LovA (ambiguous)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
dihydromonacolin L acid,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating)
Reaction(IUBMB)
dihydromonacolin L acid + O2 + [reduced NADPH---hemoprotein reductase] = monacolin L acid + [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:R10793];
(1a) dihydromonacolin L acid + O2 + [reduced NADPH---hemoprotein reductase] = 3alpha-hydroxy-3,5-dihydromonacolin L acid + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10791];
(1b) 3alpha-hydroxy-3,5-dihydromonacolin L acid = monacolin L acid + H2O (spontaneous) [RN:R10792]
Reaction(KEGG)
R10791 R10792 R10793
Substrate
dihydromonacolin L acid [CPD:C20851];
O2 [CPD:C00007];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
3alpha-hydroxy-3,5-dihydromonacolin L acid [CPD:C20852]
Product
monacolin L acid [CPD:C20853];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
3alpha-hydroxy-3,5-dihydromonacolin L acid [CPD:C20852]
Comment
A cytochrome P-450 (heme-thiolate) protein. The dehydration of 3alpha-hydroxy-3,5-dihydromonacolin L acid is believed to be spontaneous [1,2]. The enzyme from fungi also catalyses the reaction of EC 1.14.14.125, monacolin L hydroxylase [3].
History
EC 1.14.14.124 created 2014 as EC 1.14.13.197, transferred 2018 to EC 1.14.14.124
Pathway
ec00997  Biosynthesis of various other secondary metabolites
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K20980  dihydromonacolin L/monacolin L hydroxylase
Reference
1  [PMID:2921224]
  Authors
Treiber LR, Reamer RA, Rooney CS, Ramjit HG
  Title
Origin of monacolin L from Aspergillus terreus cultures.
  Journal
J Antibiot (Tokyo) 42:30-6 (1989)
DOI:10.7164/antibiotics.42.30
Reference
2  [PMID:2276977]
  Authors
Nakamura T, Komagata D, Murakawa S, Sakai K, Endo A
  Title
Isolation and biosynthesis of 3 alpha-hydroxy-3,5-dihydromonacolin L.
  Journal
J Antibiot (Tokyo) 43:1597-600 (1990)
DOI:10.7164/antibiotics.43.1597
Reference
3  [PMID:21495633]
  Authors
Barriuso J, Nguyen DT, Li JW, Roberts JN, MacNevin G, Chaytor JL, Marcus SL, Vederas JC, Ro DK
  Title
Double oxidation of the cyclic nonaketide dihydromonacolin L to monacolin J by a single cytochrome P450 monooxygenase, LovA.
  Journal
J Am Chem Soc 133:8078-81 (2011)
DOI:10.1021/ja201138v
  Sequence
[ag:AAD34552]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.124
IUBMB Enzyme Nomenclature: 1.14.14.124
ExPASy - ENZYME nomenclature database: 1.14.14.124
BRENDA, the Enzyme Database: 1.14.14.124

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Pathway (7)   
   KEGG PATHWAY (6)   
   KEGG MODULE (1)   
Chemical substance (7)   
   KEGG COMPOUND (7)   
Chemical reaction (6)   
   KEGG REACTION (3)   
   KEGG RCLASS (3)   
Gene (2)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (1)   
Protein sequence (6)   
   UniProt (3)   
   SWISS-PROT (3)   
Protein domain (4)   
   InterPro (4)   
All databases (32)   

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