Fluoroacetyl-CoA thioesterase

Fluoroacetyl-CoA thioesterase
Identifiers
EC no.3.1.2.29
Databases
BRENDAenzyme data
ExPASyNiceZyme view
KEGGenzyme entry
MetaCycmetabolic pathway
Rheareactions
PDB structuresRCSB PDB PDBe PDBsum
Search
PMCarticles
PubMedarticles
NCBIproteins

The enzyme fluoroacetyl-CoA thioesterase (EC 3.1.2.29; systematic name fluoroacetyl-CoA hydrolase) catalyses the following reaction:

fluoroacetyl-CoA
 
 
H2O
 
Rightward reaction arrow with minor substrate(s) from top left
 
 
 
+
 

The enzyme characterised from the plant Dichapetalum cymosum and the bacterium Streptomyces cattleya hydrolyses fluoroacetyl-CoA to coenzyme A and fluoroacetic acid, which form the thioester in the starting material.[1][2][3]

Dichapetalum cymosum is native to northern parts of Southern Africa and is a common cause of lethal cattle poisoning owing to the content of fluoroacetic acid in its leaves.[4] Fluoroacetate is extremely toxic to most organisms. The enzyme ensures that any fluoroacetyl-CoA produced by normal metabolic processes that use acetyl-CoA cannot go on to be incorporated into fluorocitric acid by citrate synthase.[5]

References

  1. ↑ Meyer JJ, Grobbelaar N, Vleggaar R, Louw AI (1992). "Fluoroacetyl-coenzyme-A hydrolase-like activity in Dichapetalum cymosum". J. Plant Physiol. 139 (3): 369–372. Bibcode:1992JPPhy.139..369M. doi:10.1016/s0176-1617(11)80352-4.
  2. ↑ Huang F, Haydock SF, Spiteller D, Mironenko T, Li TL, O'Hagan D, Leadlay PF, Spencer JB (May 2006). "The gene cluster for fluorometabolite biosynthesis in Streptomyces cattleya: a thioesterase confers resistance to fluoroacetyl-coenzyme A". Chemistry & Biology. 13 (5): 475–84. doi:10.1016/j.chembiol.2006.02.014. PMID 16720268.
  3. ↑ Dias MV, Huang F, Chirgadze DY, Tosin M, Spiteller D, Dry EF, Leadlay PF, Spencer JB, Blundell TL (July 2010). "Structural basis for the activity and substrate specificity of fluoroacetyl-CoA thioesterase FlK". The Journal of Biological Chemistry. 285 (29): 22495–504. doi:10.1074/jbc.m110.107177. PMC 2903362. PMID 20430898.
  4. ↑ Kellerman, T.S.; Naude, T.W.; Fourie, N.; Verwoerd, D.W. (1996). "The distribution, diagnoses and estimated economic impact of plant poisonings and mycotoxicosis in South Africa". Onderstepoort Journal of Veterinary Research. 63 (2): 65–90. hdl:2263/42595. PMID 8856758.
  5. ↑ Chandra, Girish; Mahato, Gopal Kumar; Mahto, Birkishore (2024). "Biosynthesis and Synthetic Biology of Fluorinated Products in Plants". Biosynthesis of Natural Products in Plants. pp. 381–403. doi:10.1007/978-981-97-2166-5_16. ISBN 978-981-97-2165-8.