Friday, March 3, 2017

Glucose, Mannitol, Sucrose, and Raffinose

The structure of glucose.
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?”

Figure 4.11 of Intermediate Physics for Medicine and Biology, showing the diffusion constant of a molecule as a function of the size of the molecule.

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 C6H12O6 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, C6H12O6, but the arrangement of the atoms is slightly different.

Mannitol differs from glucose by having an extra two hydrogen atoms: C6H14O6. 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?

1 comment:

  1. This comment sent from Russ Hobbie: "Who knew? I sure didn’t. Must have been the people who made the original measurements (see the caption)."