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The Amino Acids and Other Ampholytes of Urine 2 244 I953 The Amino Acids and other Ampholytes of Urine 2. THE ISOLATION OF A NEW SULPHUR-CONTAINING AMINO ACID FROM CAT URINE BY R. G. WESTALL Medical Medical Unit, University College Hospital School, London, W.C. 1 (Received 1 December 1952) The application of two-way paper chromatography other amino acids. Treatment of this mixture on to the study of the amino acids excreted in human columns of the anion-exchange resin Dowex 2 urine (Dent, 1947) has facilitated the recognition yielded fractions containing felinine contaminated of the amino acidurias which are associated with only with a small proportion of another unknown certain pathological conditions. The method has amino acid designated as 'peach-spot' (on account now been applied for several years and a large ofits ninhydrin colour reaction) and which moves to number of urine samples from normal and patho- a position just above glutam.ic acid in the diagram of logical subjects has been examined (Dent & Harris, Dent (1948). Felinine and 'peach-spot' could not 1951; Crumpler, Dent, Harris & Westall, 1951). be separated by fractionation on either Zeo-Karb Datta & Harris (1951) also investigated the urinary 215 or Dowex 2 resin columns at room temperature, amino-acid patterns of other mammals and it was but separation was achieved on a Zeo-Karb 215 apparent from this study that there were wide column operated at 650 (Partridge & Brimley, 1951). variations in the pattern of amino-acid excretion to Under these conditions the 'peach-spot' substance be observed between different species. This finding was largely degraded and a decomposition product was, perhaps, not unexpected in view of the was found in the early fractions whilst felinine was different diets involved. It was, however, sur- recovered from the later fractions. prising to find that a ninhydrin-reacting substance The amino acid has not been crystallized. It was excreted by the domestic cat in quantity and by the readily soluble in water and an aqueous solution, on ocelot in lesser amount was a hitherto undescribed evaporation, formed a syrup which could not be amino acid. induced to crystallize. Addition of ethanol in small This substance, now named 'felinine'but referred amounts gave a clear thixotropic gel and further to as 'cat-spot' by Datta & Harris (1951), partially additions yielded no crystals. An opaque white overlays leucine and isoleucine on the phenol- gelatinous precipitate was formed on addition of ammonia collidine-lutidine two-way paper chro- ether to the ethanol solution, but this material had matogram, but it can be readily separated from no apparent crystalline structure. Precipitation them on a one-way chromatogram run with tert.- with acetone from the aqueous-ethanolic solution amyl alcohol. After oxidation with hydrogen provided the best method ofisolating the substance. peroxide (Dent, 1948) the spot no longer appeared in It is well known that small amounts of impurities its original position on two-dimensional chromato- inhibit the crystallization of certain amino acids grams but in the presence of other amino acids it but, in this case, such an explanation would appear was difficult to decide whether it had moved to a new unlikely. Samples from three separate isolations of position or whether it had been degraded to such an the amino acid from different collections of cat extent that it failed to give a ninhydrin colour. urine have all yielded analyses which agree within However, the suspicion remained that felinine was very narrow limits. a new sulphur-containing amino acid. The following The simplest empirical formula that could be sulphur-containingamino acidswererunontwo-way derived was C8H1703NS (mol.wt. 207) and a deter- chromatograms: homocysteine, homomethionine, mination of the molecular weight (240) by freezing- lanthionine, ,p-dimethylcysteine, ,BB,','-tetra- point depression in water indicated that this methylcystine and the series of normal C1-C6 formula was reasonable. Since this substance was S-alkylcysteines. However, the ninhydrin-sprayed retained (in quantity) by both cation- and anion- spots due to these substances failed, in every exchange resins it was inferred that it possessed a instance, to match the position of felinine. basic group and at least one acidic group. The total The pure amino acid has now been isolated from nitrogen (Dumas) could be entirely accounted for cat urine by fractionation on ion-exchange columns as NH2-N by the nitrous acid method and an (Westall, 1952). Felinine was recovered from the equivalent ofcarbon dioxide was liberated using the primary fractionation on Zeo-Karb 215 mixed with ninhydrin-carbon dioxide method with a citrate Vol. 55 NEW AMINO ACID FROM CAT URINE. 245 buffer at pH 2-5. The material when run on the two- Treatment with Raney nickel way chromatograms in the presence of copper carbonate (Crumpler & Dent, 1949) formed a copper Distillation of an aqueous solution of felinine in complex and failed to give a ninhydrin spot. It was the presence ofRaney nickel yielded water, together thusreasonable to suppose thatthe substance was an with a small quantity of a colourless liquid which x-amino acid. formed anupper layer. This substance was identified as isoamyl alcohol by formation of a 3:5-dinitro- benzoate and by oxidation with dilute chromic acid Oxidation of the amino acid to isovaleraldehyde which gave a crystalline As the felinine contained sulphur, the change in derivative with 2:4-dinitrophenylhydrazine. Alanine position on a chromatogram of the ninhydrin spot was isolated from the reaction residue and proved to after treatment with hydrogen peroxide was be the only ninhydrin-reacting substance present. probably due to oxidation ofa sulphur atom. Fig. 1 From the evidence gained in the reaction with Raney nickel it is reasonable to assume that felinine contains cysteine linked to i8oamyl alcohol by its sulphur atom (I). This structure is provisional. H02C*CH(NH2) .CH2 .8.C(CH,)2.0CH2.CH20H (1) Phe Tyr Degradation of the amino acid When felinine was heated with concentrated gLeu hydrochloric acid some ofthe original substance was F-S found unchanged, together with traces of cystine ce3VaI and cysteine, whilst a second unknown sulphur- V containing amino acid was produced in fair yield (approx. 40 %). A brown oily substance was also C/2d%AIa Gly e liberated. The amino acids were fractionated first on On~~~~~~' a column of Zeo-Karb 215 and then on a column of (Z)~~~ Dowex 2 and the hydrolysis product (C/2) crystal- lized. Analyses gave the empirical formula C11H"|04N2S2. When run' on a two-way paper 9 < Pheno chromatogramusingphenol-ammonia and collidine- lutidine the C/2 substance moved to a position close to alanine (Fig. 1). No Fig. 1. A two-way paper chromatogram showing the ninhydrin-colouring relative positions of felinine and its derivatives. Ala, spot was observed in this solvent system after alanine; C/2, C/2 substance; F, felinine; F-S, felinine oxidation of the substance with hydrogen peroxide. sulphone; Gly, glycine; Leu, leucine; Phe, phenylalanine; The oxidation product decomposes in phenol but it Val, valine; Tyr, tyrosine. survived after running on paper with a butanol- acetic acid mixture (Partridge, 1948) and had shows the position of its oxidation product in Rp 0.10. Treatment ofan aqueous solution ofthe C/2 relation to several other amino acids. The substance substance with Raney nickel gave alanine in good was partly oxidized by air during chromatography, yield as the only surviving ninhydrin-reacting and faint spots were frequently observed on the substance. chromatograms after treatment with ninhydrin. Treatment of felinine with 2N-sodium hydroxide One of these spots appeared to be due to oxidation at 1000 destroyed the amino acid and no substance during the drying off of phenol before rerunnmg remained which would yield a ninhydrin-reacting in the collidine-lutidine solvent mixture, whilst spot. All the nitrogen, presumably as amxmonia, was another could be due to the formation of a sul- trapped in acid when the substance was distilled in phoxide. A compound C8H1705NS formed by the presence of 2N-sodium hydroxide. oxidation of felinine with hydrogen peroxide has In anattempt to explain the series ofdegradations been isolated. Analysis indicated that the original which occur when felinine is hydrolysed with acid substance had taken up two atoms of oxygen with the following scheme, based on the assumption that the probable formation of a sulphone. This idea was formula I represents the--general structure, is supported by the observation that equimolar provisionally suggested. quantities of felinine and methionine took up the Underthe treatment with acid some of the felinine same amount (2.2 atoms/mol.) of oxygen from breaks down with the liberation offree cysteine (II). potassium permanganate. The oxidized derivative The cysteine then condenses with the unchanged decomposed vigorously at 120-125' and slowly felinine elirminating water and forming a di-cysteine darkened on storage at room temperature. derivative (C/2) (III). This derivative would have 246 R. G. WESTALL I953 the found empirical formula (C01Hn0ON2S2) and columns containing the anion-exchange resin Dowex 2. The would liberate alanine and i8opentane on treatment amino acids were displaced with 0-1N-HCI and collected in with Raney nickel. Whilst the formation of alanine 55 fractions (25 ml. each). The amino-acid composition of has been confirmed, it has not, so far, been possible these fractions is illustrated in Fig. 3. Fractions 27-45 to characterize the hydrocarbon. However, some contained felinine contaminated only with''a trace of an unknown substance which gave a peach-coloured ninhydrin further evidence for the above scheme was provided spot on the paper chromatograms. These two substances by increased production ofthe dicysteine substance formed mixed bands when fractionated on both the Zeo- by the addition of L-cysteine to the mixture before Karb 215 and Dowex 2 columns.
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