ORNITHINE AND LYSINE. 163 



CHi.(NH) 



/AlTT \ 



d-Ornithine (a-3-diaminovaleric acid), CiHitNaQi* >* /XTTT is not a primary 



COOH 



cleavage product of proteins, but is formed from arginine on boiling with baryta- 

 water. JAFFE, 1 who first discovered this body, obtained it as a cleavage product 

 from ornithuric acid, which is found in the urine of hens fed with benzoic acid. 

 The ornithine which E. FISCHER and later SORENSEN,* have prepared syn- 

 thetically yields, as shown by ELLINGER, putrescine (tetramethylenediamine), 

 C4H 8 (NH 2 ) 2 , on putrefaction. A. LOEWY and NEUBERG S have shown that 

 ornithine is split into putrescine and C0 2 in the organism of cystinuria patients. 



Ornithine is a non-crystalline substance which dissolves in water, giving an 

 alkaline reaction, and yields several crystalline salts. It is precipitated by 

 phosphotungstic acid and several metallic salts, but not by silver nitrate and 

 .baryta- water (differing from arginine). Ornithine hydrochloride is dextrorotatory; 

 the synthetically prepared one is inactive. On shaking ornithine with benzoyl 

 chloride and caustic soda it is converted into dibenzoylornithine (ornithuric 

 acid). On splitting artificially prepared racemic ornithuric acid SORENSEN has 

 shown that the naturally occurring ornithuric acid is identical with the dextro- 

 rotatory a-5-dibenzoyldiaminovaleric acid. Salts and derivatives of ornithine 

 have been described by KOSSEL and his collaborators 4 and they have given a 

 method for its isolation from mixtures. 



Diaminoacetic acid, C 2 H 6 N 2 2 =CH(NH 2 ) 2 COOH was obtained by DRECHSEL 5 

 as a cleavage product of casein by boiling with tin and hydrochloric acid. It 

 crystallizes in prisms and gives a monobenzoyl compound which is not very soluble 

 in cold water and is almost insoluble in alcohol, and can be used in the isolation 

 of the acid. 



CH 2 (NH 2 ) 



d-Lysine (a--diaminocaproicacid), C6Hi 4 N 2 02= T/T )> was first 



COOH 



obtained by DRECHSEL as a cleavage product of casein. Later he and 

 his pupils, as well as KOSSEL and others, found it among the cleavage 

 products of various proteins. It has not been detected in some vegetable 

 proteins such as the prolamines (page 106). E. SCHULZE found lysine 

 in germinating plants of the Lupinus luteus, and WINTERSTEIN found 

 it in ripe cheese. It has been obtained in largest amounts (28.8 per cent) 

 by KOSSEL and DAKIN from the protamine a-cyprinine. From a gliadin 

 which was not contaminated and which they considered as a unit substance 

 although obtained from different fractions having different solubilities 

 in alcohol, OSBORNE and LEAVENWORTH 6 found a small amount of lysine 



1 Ber. d. d. chem. Gesellsch., 10 and 11. 



2 Fischer, Ber. d. d. chem. Gesellsch, 34; Sorensen, Zeitschr. f. physiol. Chem., 44. 



3 Ellinger, Zeitschr. f. physiol. Chem., 29; Loewy and Neuberg, ibid., 43. 



4 Kossel and Weiss, Zeitschr. f. physiol. Chem., 68. 



5 Ber. d. k. sachs. Gesellsch. d. Wiss., 44 



6 Drechsel, Arch. f. (Anat. u.) Physiol., 1891, and Ber. d. d. chem. Gesellsch., 25; 

 Siegfried, Arch. f. (Anat. u.) Physiol., 1891, and Ber. d. d. chem. Gesellsch., 24; Hedin, 

 Zeitschr. f. physiol. Chem., 21; Kossel, ibid., 25; Kossel and Mathews, ibid., 25; Kossel 



