KEGG ORTHOLOGY: K12709

ORTHOLOGY: K12709

Entry

K12709                      KO

Symbol

novL, cloL, couL

Name

8-demethylnovobiocic acid synthase [EC:6.3.1.15]

Pathway

map00401

Novobiocin biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Reaction

R06776

R06777

R06778

R10453

3-dimethylallyl-4-hydroxybenzoate:3-amino-4,7-dihydroxycoumarin ligase (AMP-forming)

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00401 Novobiocin biosynthesis
    K12709  novL, cloL, couL; 8-demethylnovobiocic acid synthase
Enzymes [BR:ko01000]
6. Ligases
  6.3  Forming carbon-nitrogen bonds
   6.3.1  Acid-D-ammonia (or amine) ligases (amide synthases)
    6.3.1.15  8-demethylnovobiocic acid synthase
     K12709  novL, cloL, couL; 8-demethylnovobiocic acid synthase

Genes

SANL:

KZO11_24540

STUI:

GCM10017668_29390

SHK:	J2N69_02925

SDD:	D9753_06660

SLON:

LGI35_32545

SCAJ:

O1G22_18810

NGV:	CDO52_02200

ASIC:

Q0Z83_043110

AG:	AAF67505(novL) AAG29784(couL) AAN65228(cloL)

Reference

PMID:10770754

Authors

Steffensky M, Muhlenweg A, Wang ZX, Li SM, Heide L

Title

Identification of the novobiocin biosynthetic gene cluster of Streptomyces spheroides NCIB 11891.

Journal

Antimicrob Agents Chemother 44:1214-22 (2000)
DOI:10.1128/AAC.44.5.1214-1222.2000

Sequence

[ag:AAF67505]

Reference

PMID:12480894

Authors

Pojer F, Li SM, Heide L.

Title

Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: new insights into the biosynthesis of aminocoumarin antibiotics.

Journal

Microbiology 148:3901-11 (2002)
DOI:10.1099/00221287-148-12-3901

Sequence

[ag:AAN65228]

Reference

PMID:14622269

Authors

Schmutz E, Steffensky M, Schmidt J, Porzel A, Li SM, Heide L.

Title

An unusual amide synthetase (CouL) from the coumermycin A1 biosynthetic gene cluster from Streptomyces rishiriensis DSM 40489.

Journal

Eur J Biochem 270:4413-9 (2003)
DOI:10.1046/j.1432-1033.2003.03830.x

Sequence

[ag:AAG29784]

LinkDB

ENZYME: 6.3.1.15

Entry

EC 6.3.1.15                 Enzyme

Name

8-demethylnovobiocic acid synthase;
novL (gene name);
novobiocin ligase;
novobiocic acid synthetase (misleading);
8-desmethyl-novobiocic acid synthetase;
8-demethylnovobiocic acid synthetase;
3-dimethylallyl-4-hydroxybenzoate:3-amino-4,7-dihydroxycoumarin ligase (AMP-forming)

Class

Ligases;
Forming carbon-nitrogen bonds;
Acid-D-ammonia (or amine) ligases (amide synthases)

Sysname

4-hydroxy-3-prenylbenzoate:3-amino-4,7-dihydroxycoumarin ligase (AMP-forming)

Reaction(IUBMB)

ATP + 4-hydroxy-3-prenylbenzoate + 3-amino-4,7-dihydroxycoumarin = AMP + diphosphate + 8-demethylnovobiocic acid [RN:R10453]

Reaction(KEGG)

R10453

Substrate

ATP [CPD:C00002];
4-hydroxy-3-prenylbenzoate [CPD:C12458];
3-amino-4,7-dihydroxycoumarin [CPD:C12468]

Product

AMP [CPD:C00020];
diphosphate [CPD:C00013];
8-demethylnovobiocic acid [CPD:C20629]

Comment

The enzyme is involved in the biosynthesis of the aminocoumarin antibiotic novobiocin.

History

EC 6.3.1.15 created 2013

Pathway

ec00401

Novobiocin biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K12709

8-demethylnovobiocic acid synthase

Genes

SANL:

KZO11_24540

STUI:

GCM10017668_29390

SHK:	J2N69_02925

SDD:	D9753_06660

SLON:

LGI35_32545

SCAJ:

O1G22_18810

NGV:	CDO52_02200

ASIC:

Q0Z83_043110

Reference

1 [PMID:10801869]

Authors

Steffensky M, Li SM, Heide L

Title

Cloning, overexpression, and purification of novobiocic acid synthetase from Streptomyces spheroides NCIMB 11891.

Journal

J Biol Chem 275:21754-60 (2000)
DOI:10.1074/jbc.M003066200

Sequence

[ag:AAF67505]

Reference

2 [PMID:15218104]

Authors

Pi N, Meyers CL, Pacholec M, Walsh CT, Leary JA

Title

Mass spectrometric characterization of a three-enzyme tandem reaction for assembly and modification of the novobiocin skeleton.

Journal

Proc Natl Acad Sci U S A 101:10036-41 (2004)
DOI:10.1073/pnas.0403526101

Sequence

[ag:AAF67505]

Reference

3 [PMID:16274243]

Authors

Pacholec M, Tao J, Walsh CT

Title

CouO and NovO: C-methyltransferases for tailoring the aminocoumarin scaffold in coumermycin and novobiocin antibiotic biosynthesis.

Journal

Biochemistry 44:14969-76 (2005)
DOI:10.1021/bi051599o

Other DBs

ExplorEnz - The Enzyme Database:

6.3.1.15

IUBMB Enzyme Nomenclature:

6.3.1.15

ExPASy - ENZYME nomenclature database:

6.3.1.15

BRENDA, the Enzyme Database:

6.3.1.15

LinkDB

REACTION: R10453

Entry

R10453                      Reaction

Name

3-dimethylallyl-4-hydroxybenzoate:3-amino-4,7-dihydroxycoumarin ligase (AMP-forming)

Definition

ATP + 3-Dimethylallyl-4-hydroxybenzoate + 3-Amino-4,7-dihydroxycoumarin <=> AMP + Diphosphate + 8-Demethylnovobiocic acid

Equation

C00002 + C12458 + C12468 <=> C00020 + C00013 + C20629

Reaction class

RC00162

C12458_C20629

RC00416

C12468_C20629

Enzyme

6.3.1.15

Pathway

rn00401

Novobiocin biosynthesis

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Brite

Enzymatic reactions [BR:br08201]
6. Ligase reactions
  6.3  Forming carbon-nitrogen bonds
   6.3.1  Acid-D-ammonia (or amine) ligases (amide synthases)
    6.3.1.15
     R10453  ATP + 3-Dimethylallyl-4-hydroxybenzoate + 3-Amino-4,7-dihydroxycoumarin <=> AMP + Diphosphate + 8-Demethylnovobiocic acid

Orthology

K12709

8-demethylnovobiocic acid synthase [EC:6.3.1.15]

Other DBs

RHEA:

36702

LinkDB

DBGET integrated database retrieval system