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786 URINE.
Into a conjugated glucuronic acid, uronitrotoluolic acid (JaffIs 1
). The
glucuronic acid split off from this conjugated acid is levogyrate and hence
is not identical, but only isomeric, with the ordinary glucuronic acid.
Diindhylaminobcnzaldehyde, according to Jaff£, is converted in part
into dimethylaminobenzoglucuronic acid in rabbits. The same conjugated
glucuronic acid is also produced, according to Hildebrandt,2
from p-
dimcthijltoluidine, which is first changed into p-dimethylaminobenzoic
acid. Indol and skatol seem, as above stated (page 731), to be eliminated
in the urine partly as conjugated glucuronic acids. The mercapturic
acids, which will be mentioned below, also belong to those substances
which are conjugated with glucuronic acid, and after this conjugation
appear in the urine.
A conjugation of carbamic acid, NH2COOH, with amino-acids to form
wamino-acids, R.CH.NH.(CONH2)COOH, or their anhydrides, the
hydantoins, have also been observed in several cases, as after feeding
sarcosin, amino-benzoic acid, phenylalanine, taurine, tyrosine. It must
be remarked that according to Lippich and Dakin,3
the uramino-acids
can be easily produced as transformation products from the urea in the
concentration of the urine by the aid of heat.
Syntheses with a simultaneous acetylation are of great interest.
Such a synthesis is the formation of the mercapturic acids. These acids,
which are produced in the body of dogs after the introduction of brom-
and chlorbenzene (Baumann and Preusse, Jaff£, Friedmann 4
) are
acetylated derivatives of the protein cystine, and the acetylated brom-
phenylcysteine is CH2.S(C6H4Br).CH.NH(COCH3).COOH. Another
example of a synthesis with acetylation is the phenylaminoacetic acid,
which, as Neubauer and Warburg 5 have shown, in perfusion exper-
iments with dog’s livers, gives among other products also acetylated
phenylaminoacetic acid, C6H5.CHNH(COCH3).COOH.
The synthesis of amino-acids, with simultaneous acetylation, as
recently observed by Knoop, are of specially great interest. After the
introduction of 7-phenyl-a-keto butyric acid into the body of a dog,
the formation of the corresponding acetylated amino-acid,
C6H5.CH2 .CH2 .CHNH(COCH3 ).COOH
1
Zeitsehr. f. physiol. Chem., 2.
2
JafiY’, Zeitsehr. f. physiol. Chem., 43; Hildebrandt, Hofmeister’s Beitrage, 7.
3
Lippich, Ber. d. d. chem. Gesellsch., 41; Dakin, Journ. of biol. Chem., 8; Weiland,
Bioch. Zeitsehr., 38.
4
Baumann and Preusse, Zeitsehr. f. physiol. Chem., 5; Jaff6, Ber. d. deutsch.
chem. Gesellsch., 12; Friedmann, Hofmeister’s Beitrage, 4.
6 Neubauer and 0. Warburg, Zeitsehr. f. physiol. Chem., 70.
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