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Search The CSA
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Catalytic Site Atlas

CSA LITERATURE entry for 1uqr

E.C. name3-dehydroquinate dehydratase
SpeciesActinobacillus pleuropneumoniae (strain L20)
E.C. Number (IntEnz) 4.2.1.10
CSA Homologues of 1uqrThere are 17 Homologs
CSA Entries With UniProtID P43877
CSA Entries With EC Number 4.2.1.10
PDBe Entry 1uqr
PDBSum Entry 1uqr
MACiE Entry 1uqr

Literature Report

Introduction3-Dehydroquinate dehydratase catalyses the dehydration of 3-dehydroquinate to 3-dehydroshikimate. This reaction is part of both the biosynthetic shikimate pathway for organic compound synthesis and the catabolic quinate pathway using quinate as an energy and carbon source. These pathways are both absent in animals. Type I and type II dehydroquinases exist, with completely different mechanisms and sequences, and this enzyme in question is part of the latter class. The existence of two types allows the targeting of drugs for type II to be developed.
Mechansim3-Dehydroquinate dehydratase catalyses a trans-dehydration via an enolate intermediate. Tyr 23 acts as a general base catalyst in abstracting a proton from C2, and is assisted by having its pKa lowered by Arg 18 and Arg 107. A water molecule activated by Asn 11 is deprotonated, and protonated by Asn 11 acting as a general acid catalyst. A water molecule is then activated by Asn 11 acting as a general base catalyst to deprotonate C1 and cause loss of a water molecule from the C3 hydroxyl position by His 100 acting as a general acid catalyst. It is activated by Glu 88 through a hydrogen bonding arrangement. Release of the product follows.
Reaction

Catalytic Sites for 1uqr

Annotated By Reference To The Literature - Site 1 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluA9898macie:sideChainActivates His 100.
ArgA107107macie:sideChainActivates Tyr 23 by lowering its pKa.
HisA100100macie:sideChainActs as a general acid catalyst in donation of a proton to the substrate to form water in a condensation reaction.
ArgA1818macie:sideChainActivates Tyr 23 by lowering its pKa.
AsnA1111macie:sideChainActs as a general acid/base catalyst to activate water in proton donation and abstraction.
TyrA2323macie:sideChainActs as a general base catalyst in deprotonation of the substrate at the C2 position.

Annotated By Reference To The Literature - Site 2 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluB9898macie:sideChainError
ArgB107107macie:sideChainError
HisB100100macie:sideChainError
AsnB1111macie:sideChainError

Annotated By Reference To The Literature - Site 3 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluC9898macie:sideChainError
ArgC107107macie:sideChainError
HisC100100macie:sideChainError
ArgC1818macie:sideChainError
AsnC1111macie:sideChainError

Annotated By Reference To The Literature - Site 4 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluD9898macie:sideChainActivates His 100.
ArgD107107macie:sideChainActivates Tyr 23 by lowering its pKa.
HisD100100macie:sideChainActs as a general acid catalyst in donation of a proton to the substrate to form water in a condensation reaction.
ArgD1818macie:sideChainActivates Tyr 23 by lowering its pKa.
AsnD1111macie:sideChainActs as a general acid/base catalyst to activate water in proton donation and abstraction.
TyrD2323macie:sideChainActs as a general base catalyst in deprotonation of the substrate at the C2 position.

Annotated By Reference To The Literature - Site 5 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluE9898macie:sideChainActivates His 100.
ArgE107107macie:sideChainActivates Tyr 23 by lowering its pKa.
HisE100100macie:sideChainActs as a general acid catalyst in donation of a proton to the substrate to form water in a condensation reaction.
ArgE1818macie:sideChainActivates Tyr 23 by lowering its pKa.
AsnE1111macie:sideChainActs as a general acid/base catalyst to activate water in proton donation and abstraction.
TyrE2323macie:sideChainActs as a general base catalyst in deprotonation of the substrate at the C2 position.

Annotated By Reference To The Literature - Site 6 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluF9898macie:sideChainError
ArgF107107macie:sideChainError
HisF100100macie:sideChainError
ArgF1818macie:sideChainError
AsnF1111macie:sideChainError

Annotated By Reference To The Literature - Site 7 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluG9898macie:sideChainError
ArgG107107macie:sideChainError
HisG100100macie:sideChainError
ArgG1818macie:sideChainError
AsnG1111macie:sideChainError

Annotated By Reference To The Literature - Site 8 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluH9898macie:sideChainError
ArgH107107macie:sideChainError
HisH100100macie:sideChainError
ArgH1818macie:sideChainError
AsnH1111macie:sideChainError

Annotated By Reference To The Literature - Site 9 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluI9898macie:sideChainError
ArgI107107macie:sideChainError
HisI100100macie:sideChainError
ArgI1818macie:sideChainError
AsnI1111macie:sideChainError

Annotated By Reference To The Literature - Site 10 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluJ9898macie:sideChainActivates His 100.
ArgJ107107macie:sideChainActivates Tyr 23 by lowering its pKa.
HisJ100100macie:sideChainActs as a general acid catalyst in donation of a proton to the substrate to form water in a condensation reaction.
ArgJ1818macie:sideChainActivates Tyr 23 by lowering its pKa.
AsnJ1111macie:sideChainActs as a general acid/base catalyst to activate water in proton donation and abstraction.
TyrJ2323macie:sideChainActs as a general base catalyst in deprotonation of the substrate at the C2 position.

Annotated By Reference To The Literature - Site 11 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluK9898macie:sideChainActivates His 100.
ArgK107107macie:sideChainActivates Tyr 23 by lowering its pKa.
HisK100100macie:sideChainActs as a general acid catalyst in donation of a proton to the substrate to form water in a condensation reaction.
ArgK1818macie:sideChainActivates Tyr 23 by lowering its pKa.
AsnK1111macie:sideChainActs as a general acid/base catalyst to activate water in proton donation and abstraction.
TyrK2323macie:sideChainActs as a general base catalyst in deprotonation of the substrate at the C2 position.

Annotated By Reference To The Literature - Site 12 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluL9898macie:sideChainError
ArgL107107macie:sideChainError
HisL100100macie:sideChainError
AsnL1111macie:sideChainError

Literature References

Notes:
Maes D
Structural study of the type II 3-dehydroquinate dehydratase from Actinobacillus pleuropneumoniae.
Acta Crystallogr D Biol Crystallogr 2004 60 463-471
PubMed: 14993670
Gourley DG
The two types of 3-dehydroquinase have distinct structures but catalyze the same overall reaction.
Nat Struct Biol 1999 6 521-525
PubMed: 10360352
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