recondensation to the cyclic forms.

The aldehyde form is extremely unstable and

exists only as a transient intermediate.

Experimental evidence: Tanret provided the correct interpretation. He prepared

two isomeric forms of D- Glucose by crystallisation under different conditions:

• When D-Glucose is crystallised from water or dilute alcohol at room

temperature, -D-Glucose separates, having initial specific rotation of +112°
which changes to fixed rotation +52.5°.

• On the other hand, when crystallisation takes place from water at temperature
above 98°C, a different -form of glucose separates, having initial specific
rotation of +19° which changes to fixed rotation + 52.5°.

This work of Tanret showed that glucose exists in isomeric forms which in
solution changes into the same equilibrium mixture regardless of which form is
dissolved. In glucose solutions—approx 2/3 of the sugar exists as the -form and 1/3 as
-form, at equilibrium (Fig. 3.5).
Fig. 3.5: Pyranose and furanose forms of glucose in solution

HAWORTH PROJECTION

(a) Pyranoses: Haworth in 1929 suggested that the six-membered ring forms of the
sugars be called Pyranoses, because Pyran possesses the same ring of 5 carbons
and oxygen.

(b) Furanoses: Similarly Haworth designated sugar containing 5-membered rings

as the furanoses, because furan contains the same ring.

The Pyranose forms of the sugars are internal hemi- acetals formed by
combination of the aldehyde or ketone group of the sugar with the OH group on
the 5th carbon from the aldehyde or ketone group. Similarly, the furanose forms
of the sugars are formed by reaction between the aldehyde or ketone group with
the OH group on the 4th carbon from the aldehyde or ketone group (Fig. 3.6).

Epimers and epimerisation: Two sugars which differ from one another only in
configuration around a single carbon atom are termed Epimers.
 Examples

• Glucose and galactose are examples of an epimeric pairs which differ only
with respect of C4 (Fig. 3.7). Similarly, mannose and glucose are epimers in
respect of C2.
Epimerisation: Process by which one epimer is converted to other is called
epimerisation and it requires the enzyme epimerase, e.g. conversion of galactose to
glucose in liver