KEGG   ENZYME: 2.1.1.303Help
Entry
EC 2.1.1.303                Enzyme                                 

Name
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase;
NcsB1;
neocarzinostatin O-methyltransferase
Class
Transferases;
Transferring one-carbon groups;
Methyltransferases
BRITE hierarchy
Sysname
S-adenosyl-L-methionine:2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase
Reaction(IUBMB)
S-adenosyl-L-methionine + 2,7-dihydroxy-5-methyl-1-naphthoate = S-adenosyl-L-homocysteine + 2-hydroxy-7-methoxy-5-methyl-1-naphthoate [RN:R10963]
Reaction(KEGG)
Substrate
S-adenosyl-L-methionine [CPD:C00019];
2,7-dihydroxy-5-methyl-1-naphthoate [CPD:C20857]
Product
S-adenosyl-L-homocysteine [CPD:C00021];
2-hydroxy-7-methoxy-5-methyl-1-naphthoate [CPD:C20841]
Comment
The enzyme from the bacterium Streptomyces carzinostaticus is involved in the biosynthesis of 2-hydroxy-7-methoxy-5-methyl-1-naphthoate. This compound is part of the enediyne chromophore of the antitumor antibiotic neocarzinostatin. In vivo the enzyme catalyses the regiospecific methylation at the 7-hydroxy group of its native substrate 2,7-dihydroxy-5-methyl-1-naphthoate. In vitro it also recognizes other dihydroxynaphthoic acids and catalyses their regiospecific O-methylation.
History
EC 2.1.1.303 created 2014
Pathway
ec01059  Biosynthesis of enediyne antibiotics
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
ec01130  Biosynthesis of antibiotics
Orthology
K20421  2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase
Genes
NCY: NOCYR_3137(dnrK)
NNO: NONO_c58190
NTP: CRH09_14165 CRH09_23690 CRH09_25100 CRH09_33960
NOD: FOH10_15005 FOH10_16430
RHU: A3Q40_00430(rdmB)
DTM: BJL86_2741
SMA: SAVERM_2382
SSX: SACTE_5196 SACTE_6329
SHY: SHJG_8512 SHJG_8515
SHO: SHJGH_8272 SHJGH_8275
SALU: DC74_6556
SALL: SAZ_34135
SPRI: SPRI_3765
SLE: sle_66100(sle_66100)
NAL: B005_2465(dnrK)
SEN: SACE_4650
AMD: AMED_3230
AMN: RAM_16420
AMM: AMES_3195
AMZ: B737_3195
AOI: AORI_6472
AMYY: YIM_09465(dnrK1) YIM_15125(dnrK2)
PDX: Psed_0831
AMI: Amir_4382
SESP: BN6_04400
ACTI: UA75_06455
ACAD: UA74_06455
AHG: AHOG_06225(dnrK1)
SAQ: Sare_4955
MIL: ML5_4683
SUS: Acid_5654
 » show all
Taxonomy
Reference
1  [PMID:18387946]
  Authors
Luo Y, Lin S, Zhang J, Cooke HA, Bruner SD, Shen B
  Title
Regiospecific O-methylation of naphthoic acids catalyzed by NcsB1, an O-methyltransferase involved in the biosynthesis of the enediyne antitumor antibiotic neocarzinostatin.
  Journal
J Biol Chem 283:14694-702 (2008)
DOI:10.1074/jbc.M802206200
  Sequence
Reference
2  [PMID:19702337]
  Authors
Cooke HA, Guenther EL, Luo Y, Shen B, Bruner SD
  Title
Molecular basis of substrate promiscuity for the SAM-dependent O-methyltransferase NcsB1, involved in the biosynthesis of the enediyne antitumor antibiotic neocarzinostatin.
  Journal
Biochemistry 48:9590-8 (2009)
DOI:10.1021/bi901257q
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 2.1.1.303
IUBMB Enzyme Nomenclature: 2.1.1.303
ExPASy - ENZYME nomenclature database: 2.1.1.303
BRENDA, the Enzyme Database: 2.1.1.303

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