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1 ON THE PRODUCTS OF DIGESTION OF THE PRO- TEOLYTIC SPLEEN ENZYME ACTING IN AN ALKALINE MEDIUM. BY E. P. CATHCART, M.D., Research Student in Pathological Chemistry, Lister Institute, London. SOME two years ago Leathes(l) investigated the products formed by the action of the lieno j9 protease, the enzyme acting in an acid medium discovered by Hedin and Rowland (2) in spleen juice, and more fully investigated later by Hed in(3). It was accordingly of some interest to see whether the products resulting from digestion with the lieno a protease, the spleen enzyme acting in an alkaline medium, were similar to those discovered by Leathes. The necessary digestion was carried out with the enzyme, isolated in the manner described by Hedin in his paper, from some 25 ox spleens. The enzyme solution was then added to finely ground and well washed coagulated blood serum suspended in /0 sodium carbonate solution, to which a small quantity of toluol and chloroform had been added. After 7i- months' digestion at 370, when the increase in non-precipitable nitrogen-as tested for in the tannic acid methodwas found to have ceased, the whole digest was decanted into a large basin, faintly acidified with acetic acid, and heated for some time on a water-bath in order to coagulate any proteid left. After removal of the solid matter by filtration the filtrate gave only a slight precipitate with tannic acid. To free the fluid completely from the proteid substance it wvas fuirther treated with an excess of lead hydroxide and then filtered. On freeing the filtrate from lead by means of 112S the resulting fluid gave no precipitate withl tannic acid, only a very slight biuret reaction, no bromine, but a very well-marked Adamkiewcz-Hopkins reaction. SEPARATION OF THE PRODUCTS OF DIGESTION. I. The solution, after concentration, was precipitated with 100/o mercuric sulphate in presence of 50/0 112SO4, in order to precipitate any tryptophane present. Hopkins and Cole (4) II. After removal of the mercury from the filtrate, phospho-tungstic
2 300 E. P. CATHCART. acid was added for the purpose of separating the monamino and diamino acids. I. PRECIPITATE WITH MERCURIC SULPHATE. The precipitate formed was allowed to stand for about 12 hours, then filtered off and washed with 50/0 sulphuric acid until the filtrate gave no red colour with Millon's reagent. The mercury precipitate was then decomposed with H2S, the decomposition being carried out several tin4es, at first in cold, latterly in warm acid solution. The filtrate was next treated for the separation of cystin and tryptophane as advised by Hopkins and Cole. The two fractions were worked up separately, but with negative results in both cases. The tryptophane fraction gave the glyoxylic but not the bromine reaction; the substance which vas eventually obtained was syrup-like an'd refuised to crystallise under any conditions. The cystin precipitate, which was a very small one, gave the lead reaction, but no crystals could be found. Il. PRECIPITATE WITH PHOSPHO-TUNGSTIC ACID. (a) Diamino Fraction. The filtrate and washings from the mercury precipitate were freed from mercury by means of H2S, concentrated on the water-bath, and then whilst still hot precipitated with a hot solution of the requisite amount of phospho-tungstic acid in 5 0/o sulphuric acid. After standing for 24 hours the precipitate formed was filtered off and well washed with a solution of 30/0 phospho-tungstic acid in 5 0/s sulphuric acid and finally dried by suction. The precipitate suspended in water was decomposed with barium hydrate; during the decomposition slight evolution of ammonia was noted, filtered, and the filtrate, from which a small excess of barium was removed by sulphuric acid, then concentrated. The further treatment, for the separation of the hexone bases, was carried out according to the method of Kossel and Kutscher(5). The histidine fraction, having been precipitated with silver nitrate in the usual way, was well washed with water. The precipitate, suspended in dilute sulphuric acid, was then decomposed with sulphuretted hydrogen, the decomposition being repeated several times. The filtrate from the silver sulphide was next concentrated until its content in sulphuric acid equalled 2j 0/a, and from this solution the histidine was precipitated according to the method of Kossel and Patten(8) with mercuric sulphate. The free base thus obtained was finally converted into the bichloride.
3 SPLEEN ENZYME. Analysis grm. substance gave grm. N. N found = /0. N calculated for C6H9N3022HC1= /0. The arginine fraction obtained by the addition of an excess of satu- 'rated solution of barium hydrate to the filtrate from the histidine fraction was filtered off and well washed with baryta water and then decomposed as usual with sulphuretted hydrogen in presence of sulphuric acid. The filtrate, from which the sulphuric acid was removed, was concentrated until the solution was of the consistence of thin syrup, then exactly neutralised with nitric acid, and further concentrated and left to crystallise. The crop of crystals obtained was purified by several recrystallisations from water. Analysis grm. substance gave grm. H20 and 0X2816 grm. CO2. Found /0 H and 31 /o0 C. Calculated for C6HI4N402HN03, 6X37 0/0 H and /0 C. On testing the crystals as regards their optical activity they were found to produce no rotation. (The original mother liquor was also tested with the polariscope, it likewise was inactive.) That this was the inactive arginine nitrate was further confirmed by taking the melting point when decomposition was found to begin at 212. Kutscher7) gives 211 and )(8) found in a previous sample 210). The melting point of the active variety as given by Gulewitsch(9) is Lysin Fraction. The barium and silver in the filtrate from the arginine were removed by means of sulphuric acid and sulphuretted hydrogen respectively, the filtrate concentrated, and the base reprecipitated with phospho-tungstic acid, the resulting precipitate being as usual decomposed with baryta. The excess of baryta removed by means of CO2 from the filtrate, which was then concentrated to a syrup and treated with a saturated alcoholic solution of picric acid as long as a precipitate was formed. The picrate, which was boiled out 3 times with absolute alcohol as recommended by Kutscher and Lohmann(10), in order to remove any cholin which might be present (it may be noted here that no cholin was found), was decomposed with 100/0 hydrochloric acid, the free picric acid removed by shaking out with ether, the solution then concentrated to small volume, and the lysin bichloride allowed to crystallise out. Crystals subsequently purified by recrystallisation from alcohol. Analysis grm. gave grm. AgCI. Found Cl= /0. Calculated for C,H14N2022HCl = 32'42 0/O. 301
4 P. CATHCART. (b) Monamino Fraction. The filtrate from the precipitation of the hexone bases with phospho-tungstic acid, freed from the excess of phospho-tungstic acid by means of baryta, was concentrated, during which process some tyrosine along with a little leucine crystallised out. The soluition was eventually concentrated to dryness, the crystal mass obtained being then treated according to E. Fischer's ester method. The esters obtained were fractionally distilled in a vacuum of from mm. except in the case of the first, which chiefly consisted of ether. Fraction up to 300, mostly ether. Fraction, coming over between 30 70, likewise contained some ether. In addition, however, after saponification and concentration of the solution a small quantity of alanine was obtained. N Analy8is. O'1533 gr. substance gave 171 c.c. N HES04-= N. Calculated for C3HN02= / N. Fraction This fraction seemed to consist mainly of amidovalerianic acid, leucine, and some a-pyrrolidin carboxylic acid. In order to obtain the a-pyr. carb. acid this fraction and the following one after saponification were extracted, separately, with cold absolute alcohol (Kossel and Dakin.(4)), the alcoholic filtrates united, concentrated and then allowed to dry in a desiccator. The substance obtained was again extracted with cold alcohol and filtrate dried, this extraction was repeated a third time. The final product was converted into the hydantoin derivative, typical crystals being formed. Analysis grm. substance gave grm. EIO and grm. CO2. Found= 5'64 '/o H and /0 C. Calculated for C12EHlN202=5 57 /0 H and C. m.p. was 1430, same figure given by Fischer. This same fraction gave, after fractional crystallisation, a fair yield of crystals of amido-valerianic acid. N Analysis. 0*2441 grm. subst. gave NH3=20*3 c.c. j- H2SO4= grm.in = N. Calculated for C5H4NO2= 11'96 0/0 N. Fraction This fraction contained some amido-valerianic acid mixed with the leucine of which it seemed chiefly to consist, and as mentioned above some a-pyr. carb. acid. The leucine crystals after repeated fractional crystallisations were obtained were quite pure. Analysis. 0X1258 gri. subst. gave grm. N= /0 N. Calculated for C8H13N02= /0 N.
5 SPLEEN ENZYME. Fraction 120'-125o. This fraction was found to contain glutamic acid, phenylalanine and probably a small quantity of aspartic acid. To obtain the phenylalanine this fraction and the following one were treated, before saponification, separately of course, with 5 times their volume of water and then extracted with ether in the fashion recommended by Fischer and Abderhalden (12), After evaporation of the ether strong hvdrochloric acid was added to the residue and then the whole concentrated to dryness on the water-bath. Crystals obtained were thoroughly well washed and then converted by means of ammonia into the free amido acid; was recrystallised several times from water. Analysis grm. subst. gave grm. H20 and grm. CO2. Found=7-1 0/o H and /0 C. Calculated for C9Hj1N02=6'66 0/0H and 65'43 0/0 C. The watery solution of this fraction left after treatment with ether was saponified by means of baryta, the solution after removal of the barium with sulphuric acid was concentrated. The concenfrated solution was then treated by Kutscher's (13) zinc oxide method for the separation of aspartic and glutamic acids, mainly with the view of obtaining the first named, but the result was not very satisfactory. In a preliminary digest which I had carried out with fibrin as substrate a fairly good yield of aspartic acid was obtained. Fraction consisted mainly of glutamic acid and phenylalanine. After the removal of phenylalanine as above mentioned the fraction was saponified with baryta. After exact removal of the barium the filtrate was concentrated to a very small volunie, and a large excess of strong hydrochloric acid added. After crystallisation was complete the crystals were filtered off at the pump, and thoroughly washed with strong HCI until they were quite white. Analysis grm. subst. gave grm. AgCl _ /0 Cl. Calculated for CEH9N04HCl= /0. l.p. was 193, thus agreeing closely with the 194 of Kutscher. CONCLUSIONS. 303 The following substances have been definitely isolated from the products of digestion of coagulated blood serutn with the lieno a protease of Hedin: histidine, inactive arginine, lysin, tyrosine, leucine, alanine, amido-valerianic acid, a-pyrrolidin carboxylic acid, glutamic acid, phenylalanine, and amimonia. Aspartic acid was also probably present;
6 304 E. P. CATIWART. it is formed in a large amount at any rate on digestion of fibrin by the same enzyme. The most marked differences between the digestion carried out by Leathes and the present one are (1) the nature of the arginine (14 (Leathes had the optically active variety), and (2) in Leathes's digest there was an abundant yield of aspartic acid and little glutamic, whereas in the present case the yields are reversed. Neither Leathes nor I managed to isolate tryptophane, although we both obtained well-marked glyoxylic reactions. REFERENCES. (1) Lea thes. Journ. of Physiol. xxviii. p (2) Hedin and Rowland. Zeitsch. f. physiol. Chem. xxxii. p (3) Hedin. Journ. of Physiol. xxx. p (4) Hopkins and Cole. Ibid. xxvii. p (5) Kossel and Kutscher. Zeitsch. f. physiol. Chem. xxxi. p (6) Kossel and Patten. Ibid. xxxvir. p (7) Kutscher. Ibid. xxviii. p (8) Cathcart. Proc. Physiol. Soc. Dec. 17th, Journ. of Physiol. xxxii (9) Gulewitsch. Zeitsch. f. physiol. Chem. xxvii. p (10) Kut scher and Lohmann. Ibid. xxxtx. p (11) Kossel and Dakin. Ibid. XLI. p (12) Fischer and Abderhalden. Ibid. xxxvi. p (13) Kutscher. Ibid. xxx. p (14) Cathcart. Proc. Physiol. Soc. Mar. 18th, Journ. of Physiol. xxxii
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