Summary.
The stability of felinine, an amino acid present in feline urine, was investigated. Synthetic felinine was unstable in the urine of a selection of mammals. Felinine was found to stable in feline urine in which urea had been degraded. Synthetic felinine was found to react specifically with urea and did not react with urea analogues such as biuret or thiourea or other nucleophilic compounds such as ammonia which is more nucleophilic or acetamide and water which are less nucleophilic than urea. The reaction of urea and felinine was independent of pH over the range of 3–10. Urea did not react with N-acetyl-felinine suggesting a felinine N-terminal interaction with urea. Mass spectral analysis of the reaction products showed the presence of carbamylated felinine and fragmentation ions derived from carbamyl-felinine. The physiological relevance of felinine carbamylation is yet to be determined.
Similar content being viewed by others
References
F Aylward G Coleman DR Haisman (1967) ArticleTitleCatty odour in food: the reaction between mesityl oxide and sulphur compounds in foodstuffs Chem Ind 16 1563
HT Badings (1967) ArticleTitleCauses of ribes flavor in cheese J Dairy Sci 50 1347
KP Brand (1979) ArticleTitleTom-cat odour and other pheromones in feline reproduction Vet Sci Comm 3 125–136 Occurrence Handle10.1007/BF02268958
WL Cheuk G Finne (1984) ArticleTitleEnzymatic determination of urea and ammonia in refrigerated seafood products J Agric Food Chem 32 14–18 Occurrence Handle10.1021/jf00121a004 Occurrence Handle1:CAS:528:DyaL2cXltVSqtw%3D%3D
YH Cottam P Caley S Wamberg WH Hendriks (2002) ArticleTitleFelinine reference values for urine composition J Nutr 132 1754S–1756S Occurrence Handle12042517 Occurrence Handle1:CAS:528:DC%2BD38Xks1Kqtrc%3D
WH Hendriks DRK Harding KJ Rutherfurd-Markwick (2004) ArticleTitleIsolation and characterisation of renal metabolites of gamma-glutamylfelinylglycine in the urine of the domestic cat (Felis catus) Comp Biochem Physiol B 139 245–251 Occurrence Handle15465671 Occurrence Handle10.1016/j.cbpc.2004.07.007 Occurrence Handle1:CAS:528:DC%2BD2cXotF2itrk%3D
WH Hendriks AD Woolhouse MF Tartelin PJ Moughan (1995a) ArticleTitleSynthesis of felinine, 2-amino-7-hydroxy-5,5-dimethyl-4-thiaheptanoic acid Bioorg Chem 23 89–100 Occurrence Handle10.1006/bioo.1995.1007 Occurrence Handle1:CAS:528:DyaK2MXmt1SntL4%3D
WH Hendriks PJ Moughan MF Tarttelin AD Woolhouse (1995b) ArticleTitleFelinine: a urinary amino acid of Felidae Comp Biochem Physiol B 112 581–588 Occurrence Handle10.1016/0305-0491(95)00130-1 Occurrence Handle1:STN:280:DyaK287jsFCgtw%3D%3D
D Joulain R Laurent (1989) The catty odour in black-currant extracts versus the black-currant odour in the cat’s urine? SC Bhattacharyya N Sen KL Sethi (Eds) International Congress of Essential Oils Fragrances and Flavours Oxford IBH Publishing New Delhi
VN Lapko DL Smith JB Smith (2003) ArticleTitleMethylation and carbamylation of human gamma-crystallins Prot Sci 12 1762–1774 Occurrence Handle10.1110/ps.0305403 Occurrence Handle1:CAS:528:DC%2BD3sXlvFSjurk%3D
J Lippincott I Apostol (1999) ArticleTitleCarbamylation of cysteine: a potential artifact in peptide mapping of hemoglobins in the presence of urea Anal Biochem 267 57–64 Occurrence Handle9918655 Occurrence Handle10.1006/abio.1998.2970 Occurrence Handle1:CAS:528:DyaK1MXotlGqtw%3D%3D
PP Masson P Ohlsson I Bjorkman (1981) ArticleTitleCombined enzymic JAFFE method for determination of creatinine in serum Clin Chem 27 18–21 Occurrence Handle7449105 Occurrence Handle1:CAS:528:DyaL3MXpvFaitA%3D%3D
MJI Mattina JJ Pignatello RK Swihart (1991) ArticleTitleIdentification of volatile components of bobcat (Lynx rufus) urine J Chem Ecol 17 451–462 Occurrence Handle10.1007/BF00994344 Occurrence Handle1:CAS:528:DyaK3MXksVKms7g%3D
WA McGugan DB Emmons (1967) ArticleTitleUnusual flavor defect in cheese similar to the odor of feline urine (Felis libyca domestica) J Dairy Sci 50 1495 Occurrence Handle10.3168/jds.S0022-0302(67)87654-9
SM Rutherfurd F Zhang DRK Harding AD Woolhouse WH Hendriks (2004) ArticleTitleUse of capillary (zone) electrophoresis for determining felinine and its application to investigate the stability of felinine Amino Acids 27 49–55 Occurrence Handle15309571 Occurrence Handle10.1007/s00726-004-0095-3 Occurrence Handle1:CAS:528:DC%2BD2cXmsVKkt7k%3D
H Talke GE Schubert (1965) ArticleTitleHarnstoffbestimmung im Blut und Serum im optischen Test nach Warburg Klin Wochenschr 43 174–175 Occurrence Handle14258517 Occurrence Handle10.1007/BF01484513 Occurrence Handle1:CAS:528:DyaF2MXpt1Knug%3D%3D
G Van Driessche I Vandenberghe F Jacquemotte B Devreese JJ Van Beeumen (2002) ArticleTitleMass spectrometric identification of in vivo carbamylation of the amino terminus of Ectothiorhodospira mobilis high-potential iron-sulfur protein, isozyme 1 J Mass Spect 37 858–866 Occurrence Handle10.1002/jms.348 Occurrence Handle1:CAS:528:DC%2BD38XmvFOjtrw%3D
RG Westall (1953) ArticleTitleThe amino acids and other ampholytes of urine. 2. The isolation of a new sulphur-containing amino acid from cat urine Biochem J 55 244 Occurrence Handle13093671 Occurrence Handle1:CAS:528:DyaG2cXhtVSn
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Rutherfurd, S., Kitson, T., Woolhouse, A. et al. Felinine stability in the presence of selected urine compounds. Amino Acids 32, 235–242 (2007). https://doi.org/10.1007/s00726-006-0369-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00726-006-0369-z