Felinine

Felinine
Names
IUPAC name
(2R)-2-Amino-3-[(3-hydroxy-1,1-dimethylpropyl)thio]propanoic acid
Identifiers
471-09-0 Yes
ChEBI CHEBI:39390 Yes
ChemSpider 144304 Yes
Jmol-3D images Image
PubChem 164607
Properties
C8H17NO3S
Molar mass 207.29 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Felinine, also known as (R)-2-amino-3-(4-hydroxy-2-methylbutan-2-ylthio)propanoic acid, is a chemical compound and amino acid found in cat urine and a precursor via microbial lyase of the putative cat pheromone and thiol called 3-mercapto-3-methylbutan-1-ol (MMB).[1] [2][3] Felinine is excreted by selected Felidae species including bobcats, Chinese desert cats, the kodkod, and domestic cats. Felinine synthesis occurs in the liver through a condensation reaction of glutathione and isopentenyl pyrophosphate to form 3-mercaptobutanolglutathionine (3-MBG).[4] In the kidney 3-MBG is hydrolysed and felinine partly acetylated. Cauxin assists in the hydrolysis of the dipeptide (felinylglycine) to increase the concentration of urinary felinine.[5] Urine of domestic cats may contain a series of felinine-containing compounds including free felinine, acetylfelinine, felinylglycine and 3-MBG.[6]

See also

References

  1. ↑ Discovery of felinine: Westall, R. G. "Amino acids and other ampholytes of urine. II. Isolation of a new sulfur-containing amino acid from cat urine" Biochemical Journal (1953), 55, 244-8.
  2. ↑ W.H. Hendriks, P.J. Moughan, M.F. Tarttelin and A.D. Woolhouse (1995). "Felinine: a urinary amino acid of Felidae". Comp. Biochem. Physiol. 112B (4): 581–588.
  3. ↑ P. David Josephy (28 January 2006). Molecular Toxicology. Oxford University. p. 376. ISBN 978-0-19-977145-5. Retrieved 29 July 2013.
  4. ↑ K.J. Rutherfurd, S.M. Rutherfurd, P.J. Moughan and W.H. Hendriks (January 2002). "Isolation and Characterization of a Felinine-containing Peptide from the Blood of the Domestic Cat (Felis catus)". J. Biol. Chem. 277 (1): 114–119. doi:10.1074/jbc.M107728200. PMID 11698402.
  5. ↑ M. Miyazaki, T. Yamashita, Y. Suzuki, Y. Saito, S. Soeta, H. Taira, and A. Suzuki (October 2006). "A major urinary protein of the domestic cat regulates the production of felinine, a putative pheromone precursor". Chem. Biol. (PDF) 13 (10): 1071–1079. doi:10.1016/j.chembiol.2006.08.013. PMID 17052611.
  6. ↑ W.H. Hendriks, D.R.K. Harding and K.J. Rutherfurd-Markwick (2004). "Isolation and characterisation of renal metabolites of g-glutamylfelinylglycine in the urine of the domestic cat (Felis catus)". Comp. Biochem. Phys. 139 (2): 245–251. doi:10.1016/j.cbpc.2004.07.007. PMID 15465671.