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The structure of glucose. |
You would think by now I would know everything in
Introductory Physics for Medicine and Biology; after all, I’m one of the authors. So when thumbing through the book the other day (doesn’t everyone thumb through
IPMB when they have a spare moment?) I came across Figure 4.11, showing a
log-log plot of the
diffusion constant as a function of molecular radius. Four data points stand out—
glucose,
mannitol,
sucrose, and
raffinose—because they are plotted as open rather than solid circles. This figure was drawn originally by
Russ Hobbie and has appeared in every edition of
IPMB. I got to wondering “why did Russ choose to plot those four molecules out of the thousands available?” And then, more specifically, I found myself asking “just what is raffinose anyways?”
To figure all this out, I grabbed the textbook I read in graduate school while auditing the biochemistry class taken by Vanderbilt medical students (
Biochemistry, by the late
Geoffrey Zubay). These molecules are
carbohydrates or, more simply, sugars. Glucose is the canonical example; this six-carbon molecule C
6H
12O
6 is “the single most important substrate for energy metabolism” and in humans it is “the single most important sugar in the blood”. It usually exists in a ring conformation. It is a
monosaccharide because it consists of a single ring. Other monosaccharides are
fructose and
galactose, which all have the same formula, C
6H
12O
6, but the arrangement of the atoms is slightly different.
Mannitol differs from glucose by having an extra two hydrogen atoms: C
6H
14O
6. Technically it’s a
sugar alcohol rather than a sugar. You’d think it would act similarly to glucose, but it doesn’t. Mannitol is relatively inert in humans. It doesn’t cross the
blood-brain barrier (I discussed the implications of this
previously in this blog) and it is not reabsorbed by the
kidney like glucose is so it acts as an
osmotic diuretic. In Fig. 4.11, the mannitol and glucose data almost overlap, and it is hard to tell which data point is which. According to a paper by
Bashkatov et al. (2003), glucose has a larger diffusion coefficient than mannitol, so glucose must be the data point above and to the left, and mannitol below and to the right.
Sucrose is a
disaccharide, which means it is two monosaccharides bound together through a “
glycosidic linkage”. It’s common table sugar, and consists of a molecule of glucose bound to a molecule of fructose. Russ probably chose to plot sucrose as a typical disaccharide. Two other disaccharides he could have chosen are
lactose (glucose + galactose) and
maltose (glucose + glucose).
Raffinose is a
trisaccharide, consisting of galactose + glucose + fructose. Therefore, Russ’s choice of plotting glucose, sucrose, and raffinose makes sense: the most important monosaccharide, disaccharide, and trisaccharide. A fun fact about raffinose is that the human digestive tract does not have the
enzyme needed to digest it. However, certain gas-producing bacteria in our gut can digest it, resulting in
flatulence. You probably won’t be surprised to learn that beans often contain a lot of raffinose.
So, Russ is a clever fellow. He hid a short review of carbohydrate biochemistry in Fig. 4.11. Who knew?