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A]™ —92). The o- and p-glucuronosides were obtained as crystalline amides and triacetyl methyl esters. The relation between conjugation and deamination of p-hydroxybenzylamine and related phenolic compounds in the rabbit was investigated by Hartles and Williams (147). Their results indicated that the extent of glucuronic acid conjugation was inversely proportional to the rate of deamination with phenolic amines of the type studied. Percentages of the compounds fed which were excreted as glucuronosides were as follows: N-(p-hydroxybenzyl)acetamide (XVII), 60 ; (p-hydroxybenzyl)methylamine (XVIII), 54; p-hydroxybenzylamine (XIX), 30; p-hydroxybenzaldehyde (XX), 33; and p-hydroxybenzoic acid (XXI), 18.
Since the production of glucuronic acid was not acciompanied by an increase of urinary nitrogen when sufficient carbohydrate WBS provided, it kppeared that the organism can produce glucuronic acid from this source. After a period of fasting, simultaneous administration of glucose and sodium benzoate did not prevent increased nitrogen cataboli’sm, a fact which Quick took to indicate that the precursor of glucuronic acid probably is derived more readily from glycogen and glycogenic amino acids than from glucose.
Chemical reduction of the —NO2 group proceeds through formation of nitroso and hydroxylamino groups. - N 0 2 - — - N O - « - -NHOH—+- - N H 2 It is probable that the biological reduction follows the same course since the hydroxylamino, although not the nitroso, stage has been observed. After administration of nitrobenzene, the products found in the urine are small amounts of unchanged nitrobenzene and large amounts of p-aminophenol and its conjugates with glucuronic and sulfuric acids (261). OH OSO3H QC e H 9 O e NH2 NH 2 NH2 Q - 0 - φ *φ NO, 56 BIOCHEMISTRY OF GLUCURONIC ACID Mechanism of the conversion of nitrobenzene to p-aminophenol is still a matter of controversy.