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Search The CSA
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Catalytic Site Atlas

CSA LITERATURE entry for 1qq5

E.C. name(S)-2-haloacid dehalogenase
SpeciesXanthobacter autotrophicus (Bacteria)
E.C. Number (IntEnz) 3.8.1.2
CSA Homologues of 1qq51aq6,1jud,1qh9,1qq6,1qq7,2no4,2no5,2w11,2w43,
CSA Entries With UniProtID Q60099
CSA Entries With EC Number 3.8.1.2
PDBe Entry 1qq5
PDBSum Entry 1qq5
MACiE Entry M0036

Literature Report

IntroductionThe enzyme catalyses the hydrolytic dehalogenation of L-2-haloacid to the corresponding D-2-hydroxyacid with the inversion of the configuration at the C2 atom. The degradation of halogenated hydrocarbons used in large quantities to make solvents and plastics. In addition their stereospecificity may make them useful for the biosynthesis of chiral compounds. It is a member of the haloacid dehalogenase superfamily.
MechansimWhen the L-2-haloacid is taken into the active site its carboxyl group is recognised by Arg41 before forming a Michaelis compound with the enzyme. The substrate binding drives out a water molecule freeing Asp10's nucleophilic oxygen allowing attack on the C2 carbon via an Sn2 mechanism. Asp10 is stabilised by hydrogen bonding to Lys151, Thr14 and Ser175. Arg41 is thought to abstract the halide ion from the substrate. Ser118 serves as the main residue for stabilising the substrate carboxyl moiety in the reaction intermediate. Asn177 and Asp180 are also thought to be involved in the hydrolysis reaction.
Reaction

Catalytic Sites for 1qq5

Annotated By Reference To The Literature - Site 5 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
ArgA3939macie:sideChain
ThrA1212macie:sideChain
AspA176176macie:sideChain
PheA175175macie:sideChain
AspA88macie:sideChain
AsnA173173macie:sideChain
LysA147147macie:sideChain
AsnA115115macie:sideChain
SerA171171macie:sideChain

Annotated By Reference To The Literature - Site 6 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
ArgB3939macie:sideChain
ThrB1212macie:sideChain
AspB176176macie:sideChain
PheB175175macie:sideChain
AspB88macie:sideChain
AsnB173173macie:sideChain
LysB147147macie:sideChain
AsnB115115macie:sideChain
SerB171171macie:sideChain

Literature References

Notes:
Li YF
Crystal structures of reaction intermediates of L-2-haloacid dehalogenase and implications for the reaction mechanism.
J Biol Chem 1998 273 15035-15044
PubMed: 9614112
Ridder IS
Crystal structures of intermediates in the dehalogenation of haloalkanoates by L-2-haloacid dehalogenase.
J Biol Chem 1999 274 30672-30678
PubMed: 10521454
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