Sunday, February 1, 2009

Monosaccharides -- Structure of Glucose

Sugars are small molecules which belong to the class of carbohydrates. As the name implies, a carbohydrate is a molecule whose molecular formula can be expressed in terms of just carbon and water. For example, glucose has the formula C6(H2O)6 and sucrose (table sugar) has the formula C6(H2O)11. More complex carbohydrates such as starch and cellulose are polymers of glucose. Their formulas can be be expressed as Cn(H2O)n-1. We'll look at them in more detail next time.

The difference between a monosaccharide and a disaccharide can be seen in the following example:

A quick glance tells us that a monosaccharide has just one ring, a disaccharide has two, and a polysaccharide has many. Beyond that, though, there's another important structural feature. Look at the disaccharide and focus on the oxygen which links the two rings together. The atom above it is connected to two oxygens, both of which are in ether-type situations. The carbon and these oxygens are in an acetal linkage. (The bonds are heavier and in blue.)

If we look at the corresponding location in the monosaccharide and ask what the functional group might be, we see that it is a hemiacetal. (Here the bonds are heavier and in red.) So, another way to describe the situation is that a monosaccharide has a single ring with a hemiacetal in it, a disaccharide has two rings linked by an acetal functional group, and a polysaccharide has many rings linked by many acetal functional groups. ( Check this last statement against the polysaccharide structure above).

How about the "sugars" we saw last time with just 4 carbons. Why are they monosaccharides when there is no ring? If we consider that the OH group on the bottom carbon could form a hemiacetal with the aldehyde function, then we get a ring, and that structure fits our description of a monosaccharide.