KEGG ORTHOLOGY: K20984

ORTHOLOGY: K20984

Entry

K20984            Tight     KO

Symbol

LOVF

Name

2-methylbutanoate polyketide synthase [EC:2.3.1.244]

Pathway

map00997

Biosynthesis of various other secondary metabolites

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Module

M00893

Lovastatin biosynthesis, malonyl-CoA => lovastatin acid

Reaction

R11445

malonyl-CoA:malonyl-CoA C-acyltransferase (decarboxylating, methylating, 2-methylbutanoate-forming)

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00997 Biosynthesis of various other secondary metabolites
    K20984  LOVF; 2-methylbutanoate polyketide synthase
Enzymes [BR:ko01000]
2. Transferases
  2.3  Acyltransferases
   2.3.1  Transferring groups other than aminoacyl groups
    2.3.1.244  2-methylbutanoate polyketide synthase
     K20984  LOVF; 2-methylbutanoate polyketide synthase

Genes

AG:	AAD34559(LOVF)

Reference

PMID:10334994

Authors

Kennedy J, Auclair K, Kendrew SG, Park C, Vederas JC, Hutchinson CR

Title

Modulation of polyketide synthase activity by accessory proteins during lovastatin biosynthesis.

Journal

Science 284:1368-72 (1999)
DOI:10.1126/science.284.5418.1368

Sequence

[ag:AAD34559]

LinkDB

ENZYME: 2.3.1.244

Entry

EC 2.3.1.244                Enzyme

Name

2-methylbutanoate polyketide synthase;
LovF

Class

Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups

Sysname

acyl-CoA:malonyl-CoA C-acyltransferase (2-methylbutanoate-forming)

Reaction(IUBMB)

2 malonyl-CoA + [2-methylbutanoate polyketide synthase] + 2 NADPH + 3 H+ + S-adenosyl-L-methionine = (S)-2-methylbutanoyl-[2-methylbutanoate polyketide synthase] + 2 CoA + 2 CO2 + 2 NADP+ + S-adenosyl-L-homocysteine + H2O [RN:R11445]

Reaction(KEGG)

R11445

Substrate

malonyl-CoA [CPD:C00083];
[2-methylbutanoate polyketide synthase];
NADPH [CPD:C00005];
H+ [CPD:C00080];
S-adenosyl-L-methionine [CPD:C00019]

Product

(S)-2-methylbutanoyl-[2-methylbutanoate polyketide synthase];
CoA [CPD:C00010];
CO2 [CPD:C00011];
NADP+ [CPD:C00006];
S-adenosyl-L-homocysteine [CPD:C00021];
H2O [CPD:C00001]

Comment

This polyketide synthase enzyme forms the (S)-2-methylbutanoate side chain during lovastatin biosynthesis by the filamentous fungus Aspergillus terreus. The overall reaction comprises a single condensation reaction followed by alpha-methylation, beta-ketoreduction, dehydration, and alpha,beta-enoyl reduction.

History

EC 2.3.1.244 created 2015, modified 2016

Pathway

ec00997

Biosynthesis of various other secondary metabolites

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K20984

2-methylbutanoate polyketide synthase

Reference

1 [PMID:10334994]

Authors

Kennedy J, Auclair K, Kendrew SG, Park C, Vederas JC, Hutchinson CR

Title

Modulation of polyketide synthase activity by accessory proteins during lovastatin biosynthesis.

Journal

Science 284:1368-72 (1999)
DOI:10.1126/science.284.5418.1368

Sequence

[ag:AAD34559]

Reference

2 [PMID:21069965]

Authors

Meehan MJ, Xie X, Zhao X, Xu W, Tang Y, Dorrestein PC

Title

FT-ICR-MS characterization of intermediates in the biosynthesis of the alpha-methylbutyrate side chain of lovastatin by the 277 kDa polyketide synthase LovF.

Journal

Biochemistry 50:287-99 (2011)
DOI:10.1021/bi1014776

Sequence

[ag:AAD34559]

Other DBs

ExplorEnz - The Enzyme Database:

2.3.1.244

IUBMB Enzyme Nomenclature:

2.3.1.244

ExPASy - ENZYME nomenclature database:

2.3.1.244

BRENDA, the Enzyme Database:

2.3.1.244

LinkDB

REACTION: R11445

Entry

R11445                      Reaction

Name

malonyl-CoA:malonyl-CoA C-acyltransferase (decarboxylating, methylating, 2-methylbutanoate-forming)

Definition

2 Malonyl-CoA + Acyl-carrier protein + 2 NADPH + 2 H+ + S-Adenosyl-L-methionine <=> (S)-2-Methylbutanoyl-[acp] + 2 CoA + 2 CO2 + 2 NADP+ + S-Adenosyl-L-homocysteine + H2O

Equation

2 C00083 + C00229 + 2 C00005 + 2 C00080 + C00019 <=> C21129 + 2 C00010 + 2 C00011 + 2 C00006 + C00021 + C00001

Comment

Acy-carrier protein is acp domain of the enzyme itself [KO:K20984].

Reaction class

RC00039

C00229_C21129

Enzyme

2.3.1.244

Pathway

rn00997

Biosynthesis of various other secondary metabolites

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Module

M00893

Lovastatin biosynthesis, malonyl-CoA => lovastatin acid

Brite

Enzymatic reactions [BR:br08201]
2. Transferase reactions
  2.3  Acyltransferases
   2.3.1  Transferring groups other than aminoacyl groups
    2.3.1.244
     R11445  2 Malonyl-CoA + Acyl-carrier protein + 2 NADPH + 2 H+ + S-Adenosyl-L-methionine <=> (S)-2-Methylbutanoyl-[acp] + 2 CoA + 2 CO2 + 2 NADP+ + S-Adenosyl-L-homocysteine + H2O

Orthology

K20984

2-methylbutanoate polyketide synthase [EC:2.3.1.244]

Other DBs

RHEA:

42855

LinkDB

DBGET integrated database retrieval system