KEGG   ENZYME: 5.3.99.12
Entry
EC 5.3.99.12                Enzyme                                 
Name
lachrymatory-factor synthase;
LFS
Class
Isomerases;
Intramolecular oxidoreductases;
Other intramolecular oxidoreductases
Sysname
(E)-alk-1-en-1-SO-peroxol isomerase [(Z)-alkanethial S-oxide-forming]
Reaction(IUBMB)
(E)-alk-1-en-1-SO-peroxol = (Z)-alkanethial oxide [RN:R12914]
Reaction(KEGG)
R12914
Substrate
(E)-alk-1-en-1-SO-peroxol [CPD:C22413]
Product
(Z)-alkanethial oxide [CPD:C22415]
Comment
The enzyme is responsible for production of the irritating lachrymatory factor that is released by onions and related species when they are chopped. It acts of the product of EC 4.4.1.4, alliin lyase. The enzyme from Allium cepa (onion) acts on (E)-prop-1-en-1-SO-peroxol and produces (Z)-propanethial oxide, while the enzyme from Allium siculum (honey garlic) acts on (E)-but-1-en-1-SO-peroxol and produces (Z)-butanethial oxide.
History
EC 5.3.99.12 created 2021
Orthology
K25586  lachrymatory-factor synthase
Reference
1  [PMID:2384686]
  Authors
Norris PG, Nunn AV, Hawk JL, Cox TM.
  Title
Genetic heterogeneity in erythropoietic protoporphyria: a study of the enzymatic defect in nine affected families.
  Journal
J Invest Dermatol 95:260-3 (1990)
DOI:10.1111/1523-1747.ep12484876
Reference
2  [PMID:12384686]
  Authors
Imai S, Tsuge N, Tomotake M, Nagatome Y, Sawada H, Nagata T, Kumagai H.
  Title
Plant biochemistry: an onion enzyme that makes the eyes water.
  Journal
Nature 419:685 (2002)
DOI:10.1038/419685a
  Sequence
[ag:BAC21275]
Reference
3  [PMID:18583530]
  Authors
Eady CC, Kamoi T, Kato M, Porter NG, Davis S, Shaw M, Kamoi A, Imai S.
  Title
Silencing onion lachrymatory factor synthase causes a significant change in the sulfur secondary metabolite profile.
  Journal
Plant Physiol 147:2096-106 (2008)
DOI:10.1104/pp.108.123273
  Sequence
[ag:BAC21275]
Reference
4  [PMID:20047275]
  Authors
Kubec R, Cody RB, Dane AJ, Musah RA, Schraml J, Vattekkatte A, Block E.
  Title
Applications of direct analysis in real time-mass spectrometry (DART-MS) in Allium chemistry. (Z)-butanethial S-oxide and 1-butenyl thiosulfinates and their S-(E)-1-butenylcysteine S-oxide precursor from Allium siculum.
  Journal
J Agric Food Chem 58:1121-8 (2010)
DOI:10.1021/jf903733e
Other DBs
ExplorEnz - The Enzyme Database: 5.3.99.12
IUBMB Enzyme Nomenclature: 5.3.99.12
ExPASy - ENZYME nomenclature database: 5.3.99.12
BRENDA, the Enzyme Database: 5.3.99.12

  All links  
Chemical substance (2)   
   KEGG COMPOUND (2)   
Chemical reaction (1)   
   KEGG REACTION (1)   
Gene (2)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (1)   
All databases (5)   

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