Alcoholic Fermentation: Second Edition, 1914Harden, Arthur
Science
Alcoholic Fermentation: Second Edition, 1914
Harden, Arthur
Fermentation
The evidence for the occurrence of reaction (1) is supplied by the
experiments of Neubauer and Fromherz [1911]. Having previously
found that amino-acids undergo a change of this kind in the animal
body, Neubauer investigated their behaviour towards yeast. Taking
/dl/-phenylaminoacetic acid, C{6}H{5}·CH(NH{2})·COOH, it was found
that the changes produced were essentially the same as in the animal
body. The /l/-component of the acid was partly acetylated and partly
unchanged, whereas the /d/-component of the acid yielded benzyl
alcohol, C{6}H{5}·CH{2}·OH, phenylglyoxylic acid, C{6}H{5}·CO·COOH,
and the hydroxy-acid C{6}H{5}·CH(OH)·COOH. Since however this
hydroxy-acid was produced in the /l/-form it probably arose by the
asymmetric reduction of phenylglyoxylic acid, a reaction which can
be effected by yeast as was also found to be the case in the animal
body [see Dakin, 1912, pp. 52, 78]. Moreover it was shown that
when the effects of yeast on a ketonic acid and the corresponding
hydroxy-acid were compared, the alcohol was formed in much better
yield from the ketonic acid (70 per cent.) than from the hydroxy-acid
(3-4 per cent.), the actual example being the production of
tyrosol (p-hydroxyphenylethyl alcohol), OH·C{6}H{4}·CH{2}·CH{2}OH,
from p-hydroxyphenylpyruvic acid, OH·C{6}H{4}·CH{2}·CO·COOH,
and p-hydroxyphenyl-lactic acid, OH·C{6}H{4}·CH{2}·CH(OH)·COOH
respectively.
Neubauer by these experiments established two extremely important
points. 1. That the amino-acids actually yield the corresponding
α-ketonic acids when treated with yeast and sugar solution.
2. That the a-ketonic acids under similar conditions give the
alcohol containing one carbon atom less in good yield, whereas the
corresponding hydroxy-acids only give an extremely small amount of
these alcohols.
It is therefore probable that at an early stage in the decomposition
of the amino-acids by yeast a ketonic acid is produced, which then
undergoes further change.
The source of the oxygen required for this reaction and the mechanism
of oxidation have not yet been definitely ascertained. It is possible
[p093]
OH
╱
that hydrated imino-acids of the type R·C─COOH are first formed
╲
NH{2}
[Knoop, 1910], but these have not as yet been isolated.
Public-domain text, read in full here on John Shaqi.
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