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
Neomycin, kanamycin and gentamicin biosynthesis
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 (2012) 4046-52.
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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