KEGG   ORTHOLOGY: K21184
Entry
K21184                      KO                                     

Name
sgcC, mdpC
Definition
two-component FAD-dependent monooxygenase [EC:1.14.14.15 1.14.14.-]
Pathway
ko01059  Biosynthesis of enediyne antibiotics
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
Module
M00827  C-1027 beta-amino acid moiety biosynthesis, tyrosine => 3-chloro-4,5-dihydroxy-beta-phenylalanyl-PCP
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   01059 Biosynthesis of enediyne antibiotics
    K21184  sgcC, mdpC; two-component FAD-dependent monooxygenase
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
    1.14.14.15  (3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] monooxygenase
     K21184  sgcC, mdpC; two-component FAD-dependent monooxygenase
    1.14.14.-  
     K21184  sgcC, mdpC; two-component FAD-dependent monooxygenase
Other DBs
RN: R10731
COG: COG2368
Genes
SGB: WQO_33855
STRM: M444_37920
SRO: Sros_6973
AJA: AJAP_16305(nphA1)
SESP: BN6_39070
KPHY: AOZ06_26420 AOZ06_30980
ACTI: UA75_18095
ACAD: UA74_17570
STP: Strop_2713
SAQ: Sare_2098
AG: ABY66026(mdpC)
 » show all
Reference
  Authors
Lin S, Van Lanen SG, Shen B
  Title
Characterization of the two-component, FAD-dependent monooxygenase SgcC that requires carrier protein-tethered substrates for the biosynthesis of the enediyne antitumor antibiotic C-1027.
  Journal
J Am Chem Soc 130:6616-23 (2008)
DOI:10.1021/ja710601d
Reference
PMID:12183628 (sgcC)
  Authors
Liu W, Christenson SD, Standage S, Shen B
  Title
Biosynthesis of the enediyne antitumor antibiotic C-1027.
  Journal
Science 297:1170-3 (2002)
DOI:10.1126/science.1072110
  Sequence
[sgb:WQO_33855]

KEGG   ORTHOLOGY: K21185
Entry
K21185                      KO                                     

Name
sgcE6, mdpE6, kedE6
Definition
flavin reductase
Pathway
ko01059  Biosynthesis of enediyne antibiotics
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
Module
M00827  C-1027 beta-amino acid moiety biosynthesis, tyrosine => 3-chloro-4,5-dihydroxy-beta-phenylalanyl-PCP
M00832  Kedarcidin 2-aza-3-chloro-beta-tyrosine moiety biosynthesis, azatyrosine => 2-aza-3-chloro-beta-tyrosyl-PCP
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   01059 Biosynthesis of enediyne antibiotics
    K21185  sgcE6, mdpE6, kedE6; flavin reductase
Other DBs
RN: R11368 R11393
COG: COG1853
Genes
BGF: BC1003_1446
BXB: DR64_207(pheA2)
BGE: BC1002_1302
BPY: Bphyt_1723
PSPW: BJG93_06360
PARB: CJU94_16560
PCJ: CUJ87_06945
PMEG: FNZ07_21825
RHF: EUB48_08835
BRS: S23_66080
BRAD: BF49_3457
TMR: Tmar_0112
SGB: WQO_33985
SFI: SFUL_4665
STRM: M444_37995
SRJ: SRO_1836
ART: Arth_2570
LMOI: VV02_20445
KFL: Kfla_5529
NDA: Ndas_1186
SRO: Sros_6997
FAL: FRAAL6129(bfl)
NML: Namu_5120
AMD: AMED_6862
AMN: RAM_35210
AMM: AMES_6757
AMZ: B737_6757
AOI: AORI_1842
AMYY: YIM_40775(hsaB2)
AORI: SD37_32000
PDX: Psed_3092
ACTI: UA75_19065
ACAD: UA74_18575
AHG: AHOG_16575(nphA2)
ALO: CRK57496
SAQ: Sare_0553
CAI: Caci_6349
RXY: Rxyl_0953
AG: AAQ17112(mdpE6) AFV52147(kedE6)
 » show all
Reference
PMID:12183628 (sgcE6)
  Authors
Liu W, Christenson SD, Standage S, Shen B
  Title
Biosynthesis of the enediyne antitumor antibiotic C-1027.
  Journal
Science 297:1170-3 (2002)
DOI:10.1126/science.1072110
  Sequence
[sgb:WQO_33985]
Reference
  Authors
Van Lanen SG, Lin S, Horsman GP, Shen B
  Title
Characterization of SgcE6, the flavin reductase component supporting FAD-dependent halogenation and hydroxylation in the biosynthesis of the enediyne antitumor antibiotic C-1027.
  Journal
FEMS Microbiol Lett 300:237-41 (2009)
DOI:10.1111/j.1574-6968.2009.01802.x
Reference
  Authors
Chang CY, Lohman JR, Cao H, Tan K, Rudolf JD, Ma M, Xu W, Bingman CA, Yennamalli RM, Bigelow L, Babnigg G, Yan X, Joachimiak A, Phillips GN Jr, Shen B
  Title
Crystal Structures of SgcE6 and SgcC, the Two-Component Monooxygenase That Catalyzes Hydroxylation of a Carrier Protein-Tethered Substrate during the Biosynthesis of the Enediyne Antitumor Antibiotic C-1027 in Streptomyces globisporus.
  Journal
Biochemistry 55:5142-54 (2016)
DOI:10.1021/acs.biochem.6b00713

KEGG   ENZYME: 1.14.14.15
Entry
EC 1.14.14.15               Enzyme                                 

Name
(3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] monooxygenase;
SgcC
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
(3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2],FADH2:oxygen oxidoreductase (5-hydroxylating)
Reaction(IUBMB)
(3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] + FADH2 + O2 = (3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] + FAD + H2O
Reaction(KEGG)
(other) R10731
Substrate
(3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2];
FADH2 [CPD:C01352];
O2 [CPD:C00007]
Product
(3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2];
FAD [CPD:C00016];
H2O [CPD:C00001]
Comment
The enzyme from the bacterium Streptomyces globisporus is involved in the biosynthesis of the (S)-3-chloro-5-hydroxy-beta-tyrosine moiety prior to incorporation into the chromoprotein antitumor antibiotic C-1027.
History
EC 1.14.14.15 created 2014
Pathway
ec01059  Biosynthesis of enediyne antibiotics
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K21184  two-component FAD-dependent monooxygenase
Genes
SGB: WQO_33855
STRM: M444_37920
SRO: Sros_6973
AJA: AJAP_16305(nphA1)
SESP: BN6_39070
KPHY: AOZ06_26420 AOZ06_30980
ACTI: UA75_18095
ACAD: UA74_17570
STP: Strop_2713
SAQ: Sare_2098
 » show all
Reference
1  [PMID:18426211]
  Authors
Lin S, Van Lanen SG, Shen B
  Title
Characterization of the two-component, FAD-dependent monooxygenase SgcC that requires carrier protein-tethered substrates for the biosynthesis of the enediyne antitumor antibiotic C-1027.
  Journal
J Am Chem Soc 130:6616-23 (2008)
DOI:10.1021/ja710601d
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.15
IUBMB Enzyme Nomenclature: 1.14.14.15
ExPASy - ENZYME nomenclature database: 1.14.14.15
BRENDA, the Enzyme Database: 1.14.14.15

KEGG   REACTION: R10731
Entry
R10731                      Reaction                               

Name
(3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein],FADH2:oxygen oxidoreductase (5-hydroxylating)
Definition
(S)-3-Chloro-beta-tyrosyl-[pcp] + FADH2 + Oxygen <=> (S)-3-Chloro-4,5-dihydroxy-beta-phenylalanyl-[pcp] + FAD + H2O
Equation
Reaction class
RC00046  C11449_C20810
RC00126  C00016_C01352
Enzyme
Pathway
rn01059  Biosynthesis of enediyne antibiotics
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00827  C-1027 beta-amino acid moiety biosynthesis, tyrosine => 3-chloro-4,5-dihydroxy-beta-phenylalanyl-PCP
Orthology
K21184  two-component FAD-dependent monooxygenase [EC:1.14.14.15 1.14.14.-]

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