DB code: D00283

RLCP classification 4.1034.769660.650 : Addition
8.113.594730.651 : Isomerization
CATH domain 3.30.390.10 : Enolase-like; domain 1
3.20.20.120 : TIM Barrel Catalytic domain
E.C. 5.5.1.7
CSA
M-CSA
MACiE

CATH domain Related DB codes (homologues)
3.20.20.120 : TIM Barrel D00261 D00273 D00282
3.30.390.10 : Enolase-like; domain 1 D00261 D00273 D00282

Uniprot Enzyme Name
UniprotKB Protein name Synonyms RefSeq Pfam
P05404 Chloromuconate cycloisomerase
EC 5.5.1.7
Muconate cycloisomerase II
YP_025386.1 (Protein)
NC_005912.1 (DNA/RNA sequence)
YP_293620.1 (Protein)
NC_007337.1 (DNA/RNA sequence)
PF01188 (MR_MLE)
PF02746 (MR_MLE_N)
[Graphical View]
P27099 Chloromuconate cycloisomerase
EC 5.5.1.7
Muconate cycloisomerase II
PF02746 (MR_MLE_N)
[Graphical View]

KEGG enzyme name
chloromuconate cycloisomerase
muconate cycloisomerase II

UniprotKB: Accession Number Entry name Activity Subunit Subcellular location Cofactor
P05404 TFDD1_RALEJ 2-chloro-2,5-dihydro-5-oxofuran-2-acetate = 3- chloro-cis,cis-muconate. Manganese.
P27099 TCBD_PSESQ 2-chloro-2,5-dihydro-5-oxofuran-2-acetate = 3- chloro-cis,cis-muconate. Manganese.

KEGG Pathways
Map code Pathways E.C.
MAP00361 gamma-Hexachlorocyclohexane degradation
MAP00364 Fluorobenzoate degradation
MAP00627 1,4-Dichlorobenzene degradation

Compound table
Cofactors Substrates Products Intermediates
KEGG-id C00034 C03585 C04431 C01327 I00070 C04522
E.C.
Compound Manganese 3-Chloro-cis,cis-muconate cis-4-Carboxymethylenebut-2-en-4-olide HCl 2-Chloro-2,5-dihydro-5-oxofuran-2-enolate 2-Chloro-2,5-dihydro-5-oxofuran-2-acetate
Type heavy metal carboxyl group,halide carboxyl group,aromatic ring (with hetero atoms other than nitrogen atoms) halide
ChEBI 18291
 35154
 18291
 35154
 		1472
 1472
 		18371
 18371
 		17883
 17883
PubChem 23930
 23930
 		5280608
 5280608
 		5459914
 5459914
 		18348331
 313
 18348331
 313
1chrA01 Unbound Unbound Unbound Unbound Unbound Unbound
1chrB01 Unbound Unbound Unbound Unbound Unbound Unbound
2chrA01 Unbound Unbound Unbound Unbound Unbound Unbound
1nu5A01 Unbound Unbound Unbound Unbound Unbound Unbound
1chrA02 Bound:_MN Unbound Unbound Analogue:_CL Unbound Unbound
1chrB02 Bound:_MN Unbound Unbound Unbound Unbound Unbound
2chrA02 Bound:_MN Unbound Unbound Analogue:_CL Unbound Unbound
1nu5A02 Bound:_MN Unbound Unbound Unbound Unbound Unbound

Reference for Active-site residues
resource references E.C.
Swiss-prot;P05404, P27099 & literature [7]

Active-site residues
PDB Catalytic residues Cofactor-binding residues Modified residues Main-chain involved in catalysis Comment
1chrA01
1chrB01
2chrA01
1nu5A01
1chrA02 LYS 163;LYS 165;LYS 269;GLU 323 ASP 194;GLU 220;ASP 245(Manganese binding)
1chrB02 LYS 163;LYS 165;LYS 269;GLU 323 ASP 194;GLU 220;ASP 245(Manganese binding)
2chrA02 LYS 163;LYS 165;LYS 269;GLU 323 ASP 194;GLU 220;ASP 245(Manganese binding)
1nu5A02 LYS 163;LYS 165;LYS 269;GLU 323 ASP 194;GLU 220;ASP 245(Manganese binding)

References for Catalytic Mechanism
References Sections No. of steps in catalysis
[6]
p.10400-10401
[7]
Fig.1, p.132-135
[8]
Fig.7, p.4558-4559
[12]
p.1857-1858

References
[1]
Resource
Comments X-RAY CRYSTALLOGRAPHY (3.0 ANGSTROMS)
Medline ID
PubMed ID
Journal Acta Crystallogr D Biol Crystallogr
Year 1994
Volume 50
Pages 75-84
Authors Hoier H, Schloemann M, Hammer A, Glusker JP, Carrell HL, Goldman A, Stezowski JJ, Heinemann U
Title Crystal structure of chloromuconate cycloisomerase from Alcaligenes eutrophus JMP134 (pJP4) at 3-A resolution.
Related PDB 1chr
Related UniProtKB P05404
[2]
Resource
Comments
Medline ID
PubMed ID 8110801
Journal Biochemistry
Year 1994
Volume 33
Pages 1961-70
Authors Mazur P, Pieken WA, Budihas SR, Williams SE, Wong S, Kozarich JW
Title Cis,cis-muconate lactonizing enzyme from Trichosporon cutaneum: evidence for a novel class of cycloisomerases in eucaryotes.
Related PDB
Related UniProtKB
[3]
Resource
Comments
Medline ID
PubMed ID 8021223
Journal J Bacteriol
Year 1994
Volume 176
Pages 4366-75
Authors Vollmer MD, Fischer P, Knackmuss HJ, Schlomann M
Title Inability of muconate cycloisomerases to cause dehalogenation during conversion of 2-chloro-cis,cis-muconate.
Related PDB
Related UniProtKB
[4]
Resource
Comments
Medline ID
PubMed ID 7493952
Journal J Biol Chem
Year 1995
Volume 270
Pages 29229-35
Authors Blasco R, Wittich RM, Mallavarapu M, Timmis KN, Pieper DH
Title From xenobiotic to antibiotic, formation of protoanemonin from 4-chlorocatechol by enzymes of the 3-oxoadipate pathway.
Related PDB
Related UniProtKB
[5]
Resource
Comments X-RAY CRYSTALLOGRAPHY (3.0 ANGSTROMS)
Medline ID
PubMed ID
Journal Acta Crystallogr D Biol Crystallogr
Year 1996
Volume 52
Pages 858-63
Authors Kleywegt GJ, Jones TA
Title A re-evaluation of the crystal structure of chloromuconate cycloisomerase.
Related PDB 2chr
Related UniProtKB P05404
[6]
Resource
Comments
Medline ID
PubMed ID 9724714
Journal Proc Natl Acad Sci U S A
Year 1998
Volume 95
Pages 10396-401
Authors Hasson MS, Schlichting I, Moulai J, Taylor K, Barrett W, Kenyon GL, Babbitt PC, Gerlt JA, Petsko GA, Ringe D
Title Evolution of an enzyme active site: the structure of a new crystal form of muconate lactonizing enzyme compared with mandelate racemase and enolase.
Related PDB
Related UniProtKB
[7]
Resource
Comments
Medline ID
PubMed ID 10336378
Journal Proteins
Year 1999
Volume 34
Pages 125-36
Authors Schell U, Helin S, Kajander T, Schlomann M, Goldman A
Title Structural basis for the activity of two muconate cycloisomerase variants toward substituted muconates.
Related PDB
Related UniProtKB
[8]
Resource
Comments
Medline ID
PubMed ID 11443090
Journal J Bacteriol
Year 2001
Volume 183
Pages 4551-61
Authors Kaulmann U, Kaschabek SR, Schlomann M
Title Mechanism of chloride elimination from 3-chloro- and 2,4-dichloro-cis,cis-muconate: new insight obtained from analysis of muconate cycloisomerase variant CatB-K169A.
Related PDB
Related UniProtKB
[9]
Resource
Comments
Medline ID
PubMed ID 12218011
Journal J Bacteriol
Year 2002
Volume 184
Pages 5261-74
Authors Pollmann K, Kaschabek S, Wray V, Reineke W, Pieper DH
Title Metabolism of dichloromethylcatechols as central intermediates in the degradation of dichlorotoluenes by Ralstonia sp. strain PS12.
Related PDB
Related UniProtKB
[10]
Resource
Comments
Medline ID
PubMed ID 12218027
Journal J Bacteriol
Year 2002
Volume 184
Pages 5402-9
Authors Skiba A, Hecht V, Pieper DH
Title Formation of protoanemonin from 2-chloro-cis,cis-muconate by the combined action of muconate cycloisomerase and muconolactone isomerase.
Related PDB
Related UniProtKB
[11]
Resource
Comments
Medline ID
PubMed ID 12859183
Journal Biochemistry
Year 2003
Volume 42
Pages 8387-93
Authors Schmidt DM, Mundorff EC, Dojka M, Bermudez E, Ness JE, Govindarajan S, Babbitt PC, Minshull J, Gerlt JA
Title Evolutionary potential of (beta/alpha)8-barrels: functional promiscuity produced by single substitutions in the enolase superfamily.
Related PDB
Related UniProtKB
[12]
Resource
Comments X-RAY CRYSTALLOGRAPHY (1.95 ANGSTROMS), AND COFACTOR
Medline ID
PubMed ID 12930985
Journal Protein Sci
Year 2003
Volume 12
Pages 1855-64
Authors Kajander T, Lehtio L, Schlomann M, Goldman A
Title The structure of Pseudomonas P51 Cl-muconate lactonizing enzyme: co-evolution of structure and dynamics with the dehalogenation function.
Related PDB 1nu5
Related UniProtKB P27099

Comments
This enzyme is homologous to muconate cycloisomerase (E.C. 5.5.1.1; D00282 in EzCatDB), sharing the same reactions, although it further catalyzes dehalogenation.
According to the literature [7], [8], [12], this enzyme catalyzes the following reactions:
(A) Addition of carboxylate oxygen to the C4 double-bonded carbon, forming an enolate intermediate:
(B) Isomerization; Shift of double-bond position (from C=C-O to C-C=O):
(C) Eliminative double-bond formation; Elimination of halogen atom:
The first two reactions are the same as those by the homologous enzyme, muconate cycloisomerase (D00282 in EzCatDB). However, the mechanism of the third reaction has not been elucidated yet.

Created Updated
2004-04-06 2010-08-05