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Search The CSA
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Catalytic Site Atlas

CSA LITERATURE entry for 1q3n

E.C. name3-deoxy-8-phosphooctulonate synthase
SpeciesEscherichia coli (Bacteria)
E.C. Number (IntEnz) 2.5.1.55
CSA Homologues of 1q3nThere are 66 Homologs
CSA Entries With UniProtID P0A715
CSA Entries With EC Number 2.5.1.55
PDBe Entry 1q3n
PDBSum Entry 1q3n
MACiE Entry 1q3n

Literature Report

Introduction3-deoxy-d-manno-s-octulosonate-8-phosphate synthase from E.coli (KDOPS) is responsible for the synthesis of the named product from Phosphenol Pyruvate (PEP) and arabinose-5-phosphate (A5P). It thus plays a role in the synthesis of complex lipids for the gram negative bacterial cell wall, so is a possible target for antibiotics. It displays homology with many PEP utilising enzymes, particularly the metal dependent enzyme DAHP synthase which works by a similar mechanism.
MechansimThe reaction proceeds in a stepwise manner with initial attack from the C3 nucleophile of PEP attacking the reducing end of A5P. This forms a carbocation intermediate which is attacked by a water molecule, activated by His 202, to form a second linear intermediate which undergoes cyclisation to form the product.
Reaction

Catalytic Sites for 1q3n

Annotated By Reference To The Literature - Site 1 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
HisA202202macie:sideChainActivates a water molecule which can act as a nucleophile to attack the carbocation intermediate formed by the initial condensation of A5P and PEP.

Literature References

Notes:
Radaev S
Structure and mechanism of 3-deoxy-D-manno-octulosonate 8-phosphate synthase.
J Biol Chem 2000 275 9476-9484
PubMed: 10734095
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