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Cyclic Forms of Glucose

Internal Nucleophilic and Electrophilic Sites

Glucose includes an aldehyde group with an electrophilic carbon. Call this carbon C-1. It is also a poly-alcohol. Each of
the other carbon atoms is an alcohol carbon and bears an OH group. These are nucleophiles. When a nucleophile and an
electrophile are in the same molecule, they react together much more quickly than separate nucleophilic and
electrophilic molecules do.

Take a look at the linear form of glucose below. If the OH group on C-4 adds to the aldehyde carbon it will make a 5-
membered ring, and if the OH group on C-5 adds to C-1 it will make a 6-membered ring.

Rings smaller than 5 atoms or larger than 6 atoms are not very stable so the OH groups on C-2, C-3, and C-6 don't react
with the aldehyde carbon.

Glucose is a pretty complicated molecule with all of its functional groups. To see the reaction more clearly, The scheme
below shows only the reactive OH group on C-5 and the aldehyde group.

All the carbon atoms are free to rotate around the C-C bonds in the linear molecule and they do this rapidly. In one of the
conformations that places the oxygen near the C-1 carbon, a O-C bond can form. Both of the electrons are donated from
the nucleophilic oxygen atom. Because carbon can have a maximum of 8 electrons, when the OH group donates a pair of
electrons, electron density must shift to the carbonyl oxygen. This oxygen is then very basic and it can abstract the acidic
proton from the former alcohol oxygen atom.

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Adding to the Two Sides of the Carbonyl Group

In the scheme above, the new OH group formed from the aldehyde is on the same side as the R group (CH2OH).
Another isomer results from addition of the C-5 OH group to the other side of the flat CHO group.

Forming the 5-Membered Ring Isomers

To form the 5-membered ring isomer of glucose, the nucleophilic OH group on C-4 is the one that adds to the
electrophilic carbon at C-1. After the oxygen donates its electron pair to form the new bond, there is a proton transfer
between an acidic site and a basic site.

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When the OH group attached to C-4 adds to the other side of the carbonyl (CO) group, another isomer is formed.

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Professor Patricia Shapley, University of Illinois, 2012

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