KEGG   ENZYME: 6.1.2.2Help
Entry
EC 6.1.2.2                  Enzyme                                 

Name
nebramycin 5' synthase;
tobramycin carbamoyltransferase;
TobZ
Class
Ligases;
Forming carbon-oxygen bonds;
Acid-alcohol ligases (ester synthases)
BRITE hierarchy
Sysname
tobramycin:carbamoyl phosphate ligase (AMP,phosphate-forming)
Reaction(IUBMB)
(1) tobramycin + carbamoyl phosphate + ATP + H2O = nebramycin 5' + AMP + diphosphate + phosphate (overall reaction) [RN:R10767];
(1a) carbamoyl phosphate + ATP + H2O = diphosphate + O-carbamoyladenylate + phosphate [RN:R10541];
(1b) O-carbamoyladenylate + tobramycin = AMP + nebramycin 5'  [RN:R10543];
(2) kanamycin A + carbamoyl phosphate + ATP + H2O = 6''-O-carbamoylkanamycin A + AMP + diphosphate + phosphate (overall reaction) [RN:R10768];
(2a) carbamoyl phosphate + ATP + H2O = diphosphate + O-carbamoyladenylate + phosphate;
(2b) O-carbamoyladenylate + kanamycin A = AMP + 6''-O-carbamoylkanamycin A [RN:R10544]
Reaction(KEGG)
Substrate
tobramycin [CPD:C00397];
carbamoyl phosphate [CPD:C00169];
ATP [CPD:C00002];
H2O [CPD:C00001];
O-carbamoyladenylate [CPD:C20684];
kanamycin A [CPD:C01822]
Product
nebramycin 5' [CPD:C18001];
AMP [CPD:C00020];
diphosphate [CPD:C00013];
phosphate [CPD:C00009];
O-carbamoyladenylate [CPD:C20684];
6''-O-carbamoylkanamycin A [CPD:C20699]
Comment
Requires Fe(III). The enzyme from the bacterium Streptoalloteichus tenebrarius catalyses the activation of carbamoyl phosphate to O-carbamoyladenylate and the subsequent carbamoylation of kanamycin and tobramycin.
History
EC 6.1.2.2 created 2014
Pathway
ec00524  Neomycin, kanamycin and gentamicin biosynthesis
ec01130  Biosynthesis of antibiotics
Orthology
K20579  nebramycin 5' synthase
Reference
1  [PMID:22383337]
  Authors
Parthier C, Gorlich S, Jaenecke F, Breithaupt C, Brauer U, Fandrich U, Clausnitzer D, Wehmeier UF, Bottcher C, Scheel D, Stubbs MT
  Title
The O-carbamoyltransferase TobZ catalyzes an ancient enzymatic reaction.
  Journal
Angew Chem Int Ed Engl 51:4046-52 (2012)
DOI:10.1002/anie.201108896
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 6.1.2.2
IUBMB Enzyme Nomenclature: 6.1.2.2
ExPASy - ENZYME nomenclature database: 6.1.2.2
BRENDA, the Enzyme Database: 6.1.2.2

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