KEGG   ORTHOLOGY: K20980
Entry
K20980            Tight     KO                                     

Name
LOVA, CYP68R1
Definition
dihydromonacolin L/monacolin L hydroxylase [EC:1.14.14.124 1.14.14.125]
Pathway
ko00999  Biosynthesis of various secondary metabolites - part 1
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
Module
M00893  Lovastatin biosynthesis, malonyl-CoA => lovastatin acid
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00999 Biosynthesis of various secondary metabolites - part 1
    K20980  LOVA, CYP68R1; dihydromonacolin L/monacolin L hydroxylase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K20980  LOVA, CYP68R1; dihydromonacolin L/monacolin L hydroxylase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.124  dihydromonacolin L hydroxylase
     K20980  LOVA, CYP68R1; dihydromonacolin L/monacolin L hydroxylase
    1.14.14.125  monacolin L hydroxylase
     K20980  LOVA, CYP68R1; dihydromonacolin L/monacolin L hydroxylase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, fungi type
  CYP68 family
   K20980  LOVA, CYP68R1; dihydromonacolin L/monacolin L hydroxylase
Other DBs
RN: R10791 R10792 R10794
COG: COG2124
Genes
AG: AAD34552(LOVA)
Reference
  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

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)
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
ec00999  Biosynthesis of various secondary metabolites - part 1
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
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

KEGG   REACTION: R10792
Entry
R10792                      Reaction                               

Name
3alpha-hydroxy-3,5-dihydromonacolin L acid hydro-lyase
Definition
3alpha-Hydroxy-3,5-dihydromonacolin L acid <=> Monacolin L acid + H2O
Equation
Comment
spontaneous
the second step of two-step reaction (see R10793, R10791+R10792)
Reaction class
RC03281  C20852_C20853
Enzyme
Pathway
rn00999  Biosynthesis of various secondary metabolites - part 1
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00893  Lovastatin biosynthesis, malonyl-CoA => lovastatin acid
Orthology
K20980  dihydromonacolin L/monacolin L hydroxylase [EC:1.14.14.124 1.14.14.125]
Other DBs
RHEA: 24335

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