KEGG   ENZYME: 4.4.1.23Help
Entry
EC 4.4.1.23                 Enzyme                                 

Name
2-hydroxypropyl-CoM lyase;
epoxyalkane:coenzyme M transferase;
epoxyalkane:CoM transferase;
epoxyalkane:2-mercaptoethanesulfonate transferase;
coenzyme M-epoxyalkane ligase;
epoxyalkyl:CoM transferase;
epoxypropane:coenzyme M transferase;
epoxypropyl:CoM transferase;
EaCoMT;
2-hydroxypropyl-CoM:2-mercaptoethanesulfonate lyase (epoxyalkane-ring-forming);
(R)-2-hydroxypropyl-CoM 2-mercaptoethanesulfonate lyase (cyclizing;
(R)-1,2-epoxypropane-forming)
Class
Lyases;
Carbon-sulfur lyases;
Carbon-sulfur lyases (only sub-subclass identified to date)
BRITE hierarchy
Sysname
(R)-[or (S)-]2-hydroxypropyl-CoM:2-mercaptoethanesulfonate lyase (epoxyalkane-ring-forming)
Reaction(IUBMB)
(1) (R)-2-hydroxypropyl-CoM = (R)-1,2-epoxypropane + HS-CoM [RN:R05761];
(2) (S)-2-hydroxypropyl-CoM = (S)-1,2-epoxypropane + HS-CoM [RN:R05762]
Reaction(KEGG)
Substrate
(R)-2-hydroxypropyl-CoM [CPD:C11496];
(S)-2-hydroxypropyl-CoM [CPD:C11498]
Product
(R)-1,2-epoxypropane;
HS-CoM [CPD:C03576];
(S)-1,2-epoxypropane [CPD:C11507]
Comment
Requires zinc. Acts on both enantiomers of chiral epoxyalkanes to form the corresponding (R)- and (S)-2-hydroxyalkyl-CoM adducts. The enzyme will function with some other thiols (e.g., 2-sulfanylethanol) as the nucleophile. Uses short-chain epoxyalkanes from C2 (epoxyethane) to C6 (1,2-epoxyhexane). This enzyme forms component I of a four-component enzyme system {comprising EC 4.4.1.23 (2-hydroxypropyl-CoM lyase; component I), EC 1.8.1.5 [2-oxopropyl-CoM reductase (carboxylating); component II], EC 1.1.1.268 [2-(R)-hydroxypropyl-CoM dehydrogenase; component III] and EC 1.1.1.269 [2-(S)-hydroxypropyl-CoM dehydrogenase; component IV]} that is involved in epoxyalkane carboxylation in Xanthobacter sp. strain Py2.
History
EC 4.4.1.23 created 2001 as EC 4.2.99.19, transferred 2005 to EC 4.4.1.23
Pathway
ec00625  Chloroalkane and chloroalkene degradation
ec01120  Microbial metabolism in diverse environments
Orthology
K22363  2-hydroxypropyl-CoM lyase
Genes
XAU: Xaut_4865
MSA: Mycsm_01887
MCB: Mycch_5976
MRH: MycrhN_2949
NCA: Noca_4810
Taxonomy
Reference
1  [PMID:10411892]
  Authors
Allen JR, Clark DD, Krum JG, Ensign SA.
  Title
A role for coenzyme M (2-mercaptoethanesulfonic acid) in a bacterial pathway of aliphatic epoxide carboxylation.
  Journal
Proc Natl Acad Sci U S A 96:8432-7 (1999)
DOI:10.1073/pnas.96.15.8432
Reference
2  [PMID:11939797]
  Authors
Krum JG, Ellsworth H, Sargeant RR, Rich G, Ensign SA.
  Title
Kinetic and microcalorimetric analysis of substrate and cofactor interactions in epoxyalkane:CoM transferase, a zinc-dependent epoxidase.
  Journal
Biochemistry 41:5005-14 (2002)
DOI:10.1021/bi0255221
Reference
3  [PMID:12949106]
  Authors
Coleman NV, Spain JC.
  Title
Epoxyalkane: coenzyme M transferase in the ethene and vinyl chloride biodegradation pathways of mycobacterium strain JS60.
  Journal
J Bacteriol 185:5536-45 (2003)
DOI:10.1128/JB.185.18.5536-5545.2003
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 4.4.1.23
IUBMB Enzyme Nomenclature: 4.4.1.23
ExPASy - ENZYME nomenclature database: 4.4.1.23
UM-BBD (Biocatalysis/Biodegradation Database): 4.4.1.23
BRENDA, the Enzyme Database: 4.4.1.23
CAS: 244301-07-3

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