Alcoholic Fermentation: Second Edition, 1914Harden, Arthur
Science
Alcoholic Fermentation: Second Edition, 1914
Harden, Arthur
Fermentation
On the other hand, Harden and Young regard the acid as a diphosphoric
ester of a hexose. This view is based on the fact that when the
acid is boiled with water, or an acid, free phosphoric acid is
produced along with a levo-rotatory solution containing fructose and
possibly a small proportion of some other sugar or sugars. (Euler
and Fodor however did not obtain a hexose in this way [1911].) The
acid itself only reduces Fehling's solution after some hours in
the cold, rapidly when boiled, whereas when its solution is first
boiled, and then treated with Fehling's solution in the cold, the
products of decomposition bring about reduction in a few minutes.
The reduction brought about when the acid is boiled with Fehling's
solution is considerably less (33 per cent.) than that produced by an
equivalent amount of glucose. The behaviour of the compound towards
phenylhydrazine is also in complete agreement [p050] with this
view. Lebedeff found [1909, 1910] that the acid or its salts heated
with phenylhydrazine in presence of acetic acid gave an insoluble
compound which was ultimately found to be the /phenylhydrazine salt of
hexosemonophosphoric acid osazone/
C{6}H{5}NH·NH{2}·H{2}PO{4}·C{4}H{5}(OH){3}·
C(N{2}HC{6}H{5})CH(N{2}HC{6}H{5})
[Lebedeff, 1910; 1911, 6; Young, 1911]. After recrystallisation from
alcohol this compound forms yellow needles, melting at 151°-152°. It
is decomposed by caustic soda yielding a /sodium salt/
Na{2}PO{4}·C{4}H{5}(OH){3}·(CN{2}HC{6}H{5})·CH(N{2}HC{6}H{5})
and on boiling with caustic soda decomposes giving a hexosazone (free
from phosphorus) which is probably glucosazone, and in addition
glyoxalosazone, probably as the result of a secondary decomposition.
Towards acids it is remarkably stable yielding with hydrochloric acid
a /hexosonephosphoric ester/ from which the original osazone can be
regenerated (Lebedeff). Lebedeff at first [1910] argued from the
formation of this osazone that the original hexosephosphate contained
only one phosphoric acid group per molecule of hexose. It was however
shown by Young [1911] and subsequently confirmed by Lebedeff [1911,
6] that one molecule of phosphoric acid is split off during the
formation of the osazone, even in neutral solution. Moreover it has
been found that in the cold hexosediphosphoric acid reacts with 3
molecules of phenylhydrazine forming the /diphenylhydrazine salt of
hexosediphosphoric acid phenylhydrazone/
(C{6}H{5}NH·NH{2}·H{2}PO{4}){2}·C{6}H{7}(OH){3}·N{2}HC{6}H{5}.
This compound crystallises out when 1 volume of alcohol is added to
a solution of 3 molecules of phenylhydrazine in one of the acid and
forms colourless needles melting at 115°-117°. p-Bromophenylhydrazine
yields an analogous compound melting at 127°-128°.
Public-domain text, read in full here on John Shaqi.
Reviews
Reviews
No reviews yet
Be the first to share your thoughts on this work.
Join the Discussion
Join the discussion
Sign in to leave a comment or review.
Sign InorCreate an account