KEGG ENZYME: 6.1.2.2

ENZYME: 6.1.2.2

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)

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)

R10541 R10543 R10544 R10767 R10768;
(other) R11279

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

ec01110

Biosynthesis of secondary metabolites

Orthology

K20579

nebramycin 5' synthase

Reference

1 [PMID:22383337]