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Search The CSA
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Catalytic Site Atlas

CSA LITERATURE entry for 1jof

E.C. namecarboxy-cis,cis-muconate cyclase
SpeciesNeurospora crassa ()
E.C. Number (IntEnz) 5.5.1.5
CSA Homologues of 1jof1ri6,3fgb,3hfq,
CSA Entries With UniProtID P38677
CSA Entries With EC Number 5.5.1.5
PDBe Entry 1jof
PDBSum Entry 1jof
MACiE Entry 1jof

Literature Report

IntroductionEukaryote 3-carboxy-cis,cis-muconate lactonizing enzyme is an eukaryote muconate lactonizing enzyme(MLE), converting cis,cis-muconates to muconlactones.
It is in the class of CyclicMLE among the three classes of muconate lactonizing enzymes. The other 2 classes are bacterial CyclicMLE and bacterial MLE. The three classes of MLE are structurally very different but catalyse an analogous reaction, i.e. convergent functional evolution occurred.
MechansimThe catalysis is a general acid/base catalysis. His148 acts as a base to deprotonate the C1 carboxylate group of the substrate to allow it to nucleophilically attack the substrate carbon-4. Glu212 acts as an acid to protonate the substrate C6 carboxylate group. An enolic intermediate is formed. The protonated His148 then donates a proton to change the enolic intermediate back to a carboxylic acid. Arg196 and Arg274 increases the nucleophilicity of the substrate C1 carboxylate by hydrogen bonding.
Reaction

Catalytic Sites for 1jof

Annotated By Reference To The Literature - Site 1 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluA212213macie:sideChainA base to protonate the C6 carboxylate of the substrate to form an enolic intermediate.
HisA148149macie:sideChainA base to deprotonate the substrate C1 carboxylic acid to allow the nucleophilicattack to the C4 carbon of substrate to form an enolic intermediate. Then, acts as an acid to restore the enolic intermediate back to a carboxylic acid.
ArgA274275macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase its nucleophilicity.
ArgA196197macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase the nucleophilicity of the group

Annotated By Reference To The Literature - Site 2 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluB212213macie:sideChainA base to protonate the C6 carboxylate of the substrate to form an enolic intermediate.
HisB148149macie:sideChainA base to deprotonate the substrate C1 carboxylic acid to allow the nucleophilicattack to the C4 carbon of substrate to form an enolic intermediate. Then, acts as an acid to restore the enolic intermediate back to a carboxylic acid.
ArgB274275macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase its nucleophilicity.
ArgB196197macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase the nucleophilicity of the group

Annotated By Reference To The Literature - Site 3 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluC212213macie:sideChainA base to protonate the C6 carboxylate of the substrate to form an enolic intermediate.
HisC148149macie:sideChainA base to deprotonate the substrate C1 carboxylic acid to allow the nucleophilicattack to the C4 carbon of substrate to form an enolic intermediate. Then, acts as an acid to restore the enolic intermediate back to a carboxylic acid.
ArgC274275macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase its nucleophilicity.
ArgC196197macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase the nucleophilicity of the group

Annotated By Reference To The Literature - Site 4 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluD212213macie:sideChainA base to protonate the C6 carboxylate of the substrate to form an enolic intermediate.
HisD148149macie:sideChainA base to deprotonate the substrate C1 carboxylic acid to allow the nucleophilicattack to the C4 carbon of substrate to form an enolic intermediate. Then, acts as an acid to restore the enolic intermediate back to a carboxylic acid.
ArgD274275macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase its nucleophilicity.
ArgD196197macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase the nucleophilicity of the group

Annotated By Reference To The Literature - Site 5 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluE212213macie:sideChainA base to protonate the C6 carboxylate of the substrate to form an enolic intermediate.
HisE148149macie:sideChainA base to deprotonate the substrate C1 carboxylic acid to allow the nucleophilicattack to the C4 carbon of substrate to form an enolic intermediate. Then, acts as an acid to restore the enolic intermediate back to a carboxylic acid.
ArgE274275macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase its nucleophilicity.
ArgE196197macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase the nucleophilicity of the group

Annotated By Reference To The Literature - Site 6 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluF212213macie:sideChainA base to protonate the C6 carboxylate of the substrate to form an enolic intermediate.
HisF148149macie:sideChainA base to deprotonate the substrate C1 carboxylic acid to allow the nucleophilicattack to the C4 carbon of substrate to form an enolic intermediate. Then, acts as an acid to restore the enolic intermediate back to a carboxylic acid.
ArgF274275macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase its nucleophilicity.
ArgF196197macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase the nucleophilicity of the group

Annotated By Reference To The Literature - Site 7 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluG212213macie:sideChainA base to protonate the C6 carboxylate of the substrate to form an enolic intermediate.
HisG148149macie:sideChainA base to deprotonate the substrate C1 carboxylic acid to allow the nucleophilicattack to the C4 carbon of substrate to form an enolic intermediate. Then, acts as an acid to restore the enolic intermediate back to a carboxylic acid.
ArgG274275macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase its nucleophilicity.
ArgG196197macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase the nucleophilicity of the group

Annotated By Reference To The Literature - Site 8 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
GluH212213macie:sideChainA base to protonate the C6 carboxylate of the substrate to form an enolic intermediate.
HisH148149macie:sideChainA base to deprotonate the substrate C1 carboxylic acid to allow the nucleophilicattack to the C4 carbon of substrate to form an enolic intermediate. Then, acts as an acid to restore the enolic intermediate back to a carboxylic acid.
ArgH274275macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase its nucleophilicity.
ArgH196197macie:sideChainHydrogen bonded to the substrate C1 carboxylate group oxygen to increase the nucleophilicity of the group

Literature References

Notes:
Kajander T
The structure of Neurospora crassa 3-carboxy-cis,cis-muconate lactonizing enzyme, a beta propeller cycloisomerase.
Structure 2002 10 483-492
PubMed: 11937053
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