Alcoholic Fermentation: Second Edition, 1914Harden, Arthur
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Alcoholic Fermentation: Second Edition, 1914
Harden, Arthur
Fermentation
This change differs in principle from that assumed by Baeyer,
inasmuch as the second stage is not effected by the re-addition of
water, but by the keto-enol transformation, which is now usually
ascribed to the migration of the hydrogen atom, although the same
result can theoretically be arrived at by the addition and removal
of the elements of water. The analogy of this process to what might
be supposed to occur in the conversion of sugar into carbon dioxide
and alcohol was pointed out by Wohl and Oesterlin, and subsequently
Wohl developed a theoretical scheme of reactions by which the process
of alcoholic fermentation could be represented. In the first place
the elements of water are removed from the α and β carbon atoms of
glucose (I) and the resulting enol (II) undergoes conversion into
the corresponding ketone (III), which has the constitution of a
condensation product of methylglyoxal and glyceraldehyde, and hence
is readily resolved by hydrolysis into these compounds (IV). The
glyceraldehyde passes by a similar series of changes (V, VI) into
methylglyoxal, and this is then converted by addition of water into
lactic acid (VII), a reaction which is common to all ketoaldehydes
of this kind. Finally, the lactic acid is split up into alcohol and
carbon dioxide (VIII):--
CHO CHO CHO
│ │ │
CH(OH) H C(OH) CO
│ minus · ║ │
CH(OH) OH CH ⇌ CH{2}
│ │ │
CH(OH) CH(OH) CH(OH)
│ │ │
CH(OH) CH(OH) CH(OH)
│ │ │
CH{2}(OH) CH{2}(OH) CH{2}(OH)
I. II. III.
Glucose.
Methylglyoxal
CHO COOH CO{2}
│ │ ------
CO + H{2}O CH(OH) CH{2}OH
│ │ │
CH{3} CH{3} CH{3}
───────────────────────────────────────────────────────────
CHO CHO CHO COOH CO{2}
│ H │ │ │ ------
CH(OH) minus · C(OH) ⇌ CO + H{2}O CH(OH) CH{2}OH
│ OH ║ │ │ │
CH{2}(OH) CH{2} CH{3} CH{3} CH{3}
IV. V. VI. VII. VIII.
Glyceraldehyde. Methyl- Lactic Alcohol
glyoxal. acid. and
carbon
dioxide.
[p102]
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