KEGG   ORTHOLOGY: K15991
Entry
K15991            Tight     KO                                     
Symbol
tylHI, CYP105L1
Name
20-oxo-5-O-mycaminosyltylactone 23-monooxygenase [EC:1.14.15.34]
Pathway
map00522  Biosynthesis of 12-, 14- and 16-membered macrolides
map01052  Type I polyketide structures
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00773  Tylosin biosynthesis, methylmalonyl-CoA + malonyl-CoA => tylactone => tylosin
Reaction
R10656  20-oxo-5-O-beta-mycaminosyltylactone,reduced ferredoxin:oxygen oxidoreductase (23-hydroxylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   01052 Type I polyketide structures
    K15991  tylHI, CYP105L1; 20-oxo-5-O-mycaminosyltylactone 23-monooxygenase
   00522 Biosynthesis of 12-, 14- and 16-membered macrolides
    K15991  tylHI, CYP105L1; 20-oxo-5-O-mycaminosyltylactone 23-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   01008 Polyketide biosynthesis proteins
    K15991  tylHI, CYP105L1; 20-oxo-5-O-mycaminosyltylactone 23-monooxygenase
   00199 Cytochrome P450
    K15991  tylHI, CYP105L1; 20-oxo-5-O-mycaminosyltylactone 23-monooxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.15  With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.15.34  20-oxo-5-O-mycaminosyltylactone 23-monooxygenase
     K15991  tylHI, CYP105L1; 20-oxo-5-O-mycaminosyltylactone 23-monooxygenase
Polyketide biosynthesis proteins [BR:ko01008]
 Polyketide tailoring proteins
  Oxygenase
   K15991  tylHI, CYP105L1; 20-oxo-5-O-mycaminosyltylactone 23-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, bacteria type
  CYP105 family
   K15991  tylHI, CYP105L1; 20-oxo-5-O-mycaminosyltylactone 23-monooxygenase
Other DBs
COG: COG2124
Genes
STRE: GZL_03700
STRM: M444_29910
AG: AAD12167(tylHI)
Reference
PMID:10220165
  Authors
Fouces R, Mellado E, Diez B, Barredo JL
  Title
The tylosin biosynthetic cluster from Streptomyces fradiae: genetic organization of the left region.
  Journal
Microbiology 145 ( Pt 4):855-68 (1999)
DOI:10.1099/13500872-145-4-855
  Sequence
[ag:AAD12167]
Reference
PMID:11476481
  Authors
Rawlings BJ.
  Title
Type I polyketide biosynthesis in bacteria (part B).
  Journal
Nat Prod Rep 18:231-81 (2001)
DOI:10.1039/B100191O
Reference
PMID:10510490
  Authors
Bate N, Cundliffe E
  Title
The mycinose-biosynthetic genes of Streptomyces fradiae, producer of tylosin.
  Journal
J Ind Microbiol Biotechnol 23:118-122 (1999)
DOI:10.1038/sj.jim.2900707
LinkDB

KEGG   ENZYME: 1.14.15.34
Entry
EC 1.14.15.34               Enzyme                                 
Name
20-oxo-5-O-mycaminosyltylactone 23-monooxygenase;
tylH1 (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
20-oxo-5-O-beta-mycaminosyltylactone,reduced ferredoxin:oxygen oxidoreductase (23-hydroxylating)
Reaction(IUBMB)
20-oxo-5-O-beta-mycaminosyltylactone + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = 5-O-beta-mycaminosyltylonolide + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:R10656]
Reaction(KEGG)
R10656
Substrate
20-oxo-5-O-beta-mycaminosyltylactone [CPD:C20760];
reduced ferredoxin [iron-sulfur] cluster [CPD:C00138];
H+ [CPD:C00080];
O2 [CPD:C00007]
Product
5-O-beta-mycaminosyltylonolide;
oxidized ferredoxin [iron-sulfur] cluster [CPD:C00139];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein. Involved in the biosynthetic pathway of the macrolide antibiotic tylosin, which is produced by several species of Streptomyces bacteria.
History
EC 1.14.15.34 created 2014 as EC 1.14.13.186, transferred 2018 to EC 1.14.15.34
Pathway
ec00522  Biosynthesis of 12-, 14- and 16-membered macrolides
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K15991  20-oxo-5-O-mycaminosyltylactone 23-monooxygenase
Genes
STRE: GZL_03700
STRM: M444_29910
Reference
1  [PMID:7283418]
  Authors
Baltz RH, Seno ET
  Title
Properties of Streptomyces fradiae mutants blocked in biosynthesis of the macrolide antibiotic tylosin.
  Journal
Antimicrob Agents Chemother 20:214-25 (1981)
DOI:10.1128/AAC.20.2.214
  Sequence
[ag:AAD12167]
Reference
2  [PMID:15489173]
  Authors
Reeves CD, Ward SL, Revill WP, Suzuki H, Marcus M, Petrakovsky OV, Marquez S, Fu H, Dong SD, Katz L
  Title
Production of hybrid 16-membered macrolides by expressing combinations of polyketide synthase genes in engineered Streptomyces fradiae hosts.
  Journal
Chem Biol 11:1465-72 (2004)
DOI:10.1016/j.chembiol.2004.08.019
Other DBs
ExplorEnz - The Enzyme Database: 1.14.15.34
IUBMB Enzyme Nomenclature: 1.14.15.34
ExPASy - ENZYME nomenclature database: 1.14.15.34
BRENDA, the Enzyme Database: 1.14.15.34
LinkDB

KEGG   REACTION: R10656
Entry
R10656                      Reaction                               
Name
20-oxo-5-O-beta-mycaminosyltylactone,reduced ferredoxin:oxygen oxidoreductase (23-hydroxylating)
Definition
20-Oxo-5-O-beta-mycaminosyltylactone + 2 Reduced ferredoxin + 2 H+ + Oxygen <=> 5-O-beta-D-Mycaminosyltylonolide + 2 Oxidized ferredoxin + H2O
Equation
C20760 + 2 C00138 + 2 C00080 + C00007 <=> C12002 + 2 C00139 + C00001
Reaction class
RC03228  C12002_C20760
Enzyme
1.14.15.34
Pathway
rn00522  Biosynthesis of 12-, 14- and 16-membered macrolides
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00773  Tylosin biosynthesis, methylmalonyl-CoA + malonyl-CoA => tylactone => tylosin
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.15  With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.15.34
     R10656  20-Oxo-5-O-beta-mycaminosyltylactone + 2 Reduced ferredoxin + 2 H+ + Oxygen <=> 5-O-beta-D-Mycaminosyltylonolide + 2 Oxidized ferredoxin + H2O
Orthology
K15991  20-oxo-5-O-mycaminosyltylactone 23-monooxygenase [EC:1.14.15.34]
Other DBs
RHEA: 24527
LinkDB

DBGET integrated database retrieval system