Alcoholic Fermentation: Second Edition, 1914Harden, Arthur
Science
Alcoholic Fermentation: Second Edition, 1914
Harden, Arthur
Fermentation
As a matter of fact this substance cannot be detected among the
products of fermentation, but succinic acid as already explained is
formed. This acid might, however, possibly be formed by the oxidation
of the γ-hydroxybutyric acid:--
COOH·CH{2}·CH{2}·CH{2}·OH + 2O = COOH·CH{2}·CH{2}·COOH + H{2}O,
although this change is on biological grounds improbable.
The conversion of the group ─CH(NH{2})─ into the terminal CH{2}·OH
in fusel oil, or COOH in succinic acid, may possibly be effected in
several different ways, the most probable of which are the following:--
I. Direct elimination of carbon dioxide, followed by hydrolysis of the
resulting amine:--
(1) R·CH(NH{2})·COOH = R·CH{2}·NH{2}+ CO{2}.
(2) R·CH{2}·NH{2} + H{2}O = R·CH{2}·OH + NH{3}.
The reaction (1) is actually effected by many bacteria and has been
employed for the preparation of bases from amino-acids [cf. Barger,
1914, p. 7], although there is no direct evidence that it can be
brought about by yeast. On the other hand reaction (2) has actually
been observed with some yeasts. Thus it has been found [Ehrlich and
Pistschimuka, 1912, 1] that many "wild" yeasts produce this change
with great readiness in presence of sugar, glycerol or ethyl alcohol
as sources of carbon and grow well in media in which amines, such
as p-hydroxyphenylethylamine or iso-amylamine, form the only source
of nitrogen. /Willia anomala/ (Hansen), a yeast which forms surface
growths, succeeds admirably under these conditions, whereas culture
yeasts are much less active in this way, although they produce a
certain amount of change. It is therefore possible that this mode of
decomposition plays some part in the production of fusel oil, but in
the case of culture yeasts it is entirely subordinated to the mode
next to be discussed. [p092]
II. Oxidative removal of the ─NH{2} group with formation of an
α-ketonic acid:--
(1) R·CH(NH{2})·COOH + O = R·CO·COOH + NH{3}
followed by the decomposition of the ketonic acid into carbon dioxide
and an aldehyde and the subsequent reduction or oxidation of the
aldehyde:--
(2) R·CO·COOH = R·CHO + CO{2}.
(3) (/a/) R·CHO + 2H = R·CH{2}OH.
(/b/) R·CHO + O = R·COOH.
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