448 CHEMISTRY OF THE LEUOOMAINS. 



counted for by abnormal metabolism rather than by bacterial activity, 

 and if so, it may be possible to demonstrate the presence of the ante- 

 cedents ornithin and lysin. 



The relation of lysin to cadaverin and of the latter to piperidin 

 (p, 442), suggests a similar relation between ornithin, putrescin and 

 pyrrolidin. The carboxyl derivative of the latter has been obtained 

 from proteids and will be described next. 



a-Pyrrolidin carbonic acid, C^HgNOj, is a product ot proteid 

 cleavage which differs from all others in that it has a nitrogen con- 

 taining ring. It undoubtedly originates from and is related to the 

 hexon bases arginin, histidin and ornithin. This is seen in the fact 

 that Schulze and Winterstein obtained a pyrrolidin-like body on dry 

 distillation of arginin and of ornithin. On the other hand, although 

 this base results, according to Fischer, in the hydrolytic decomposi- 

 tion, with hydrochloric acid, of casein, egg-albumin, fibrin and gelatin 

 (Levene), it does not form when arginin or ornithin are subjected to 

 the same method. For this reason Fischer ' is inclined to consider 

 it as a primary cleavage product of proteids. It is conceivable, how- 

 ever, that this base may originate in the cleavage of histidin or its 

 parent substance (p. 442) under conditions similar to the forma- 

 tion of uric acid out of hypoxanthin or out of thymus gland (p. 344), 

 in which case urea would be split off and the chain would then re- 

 close to form the pyrrolidin carbonic acid. 



The presumed formation of this base from ornithin can be ex- 

 pressed by the following equation : 



CH,— CHj 



NH,.CH,.CH,.CH,.CH(NH,).COOH = CH. CH.COOH -f-NH,. 



NH 



This equation should be compared with those for piperidin and his- 

 tidin on page 442. It is noteworthy that this acid is closely related 

 to the cleavage products of atropin and cocain, namely tropic and 

 hygrinic acids. Moreover, as indicating the possibility of its being 

 a secondary product of proteid cleavage may be mentioned the fact 

 that a methyl 1-4 di-amido valerianic acid on treatment with hydro- 

 chloric acid yields a methyl pyrrolidin carbonic acid (Wildstatter 

 and Ettlinger^"). 



The synthesis of a-pyrrolidin carbonic acid has been effected in- 

 dependently by Wildstatter' and by Fischer.* As in the case of 

 ornithin the synthetic body is the racemic form whereas the natural 

 product is both active and inactive. Thus, from casein Fischer ob- 



^Zeits. phydol. Ohem., 33, 152, 163, 412. 

 'Berkkte, 35,620. 

 "Seriehte, 33, 1160. 

 ^Serichte, 34,454(1901). 



