2012: Advent Chemistry: N-glucoside

by on December 24, 2012

Well, it’s the 24th of December, the last day of Advent. We’ve looked at some of the fundamentals of organic chemistry: bonds, functional groups, resonance (“shuffling electrons around”), aromaticity, chirality, conformation (shape) and stability, along with some other aspects of chemistry like ionic bonds and phases of matter.

Today’s molecule, to finish the adventure, is something which seems very appropriate for the eve of a major feast.

N-glucosides are formed when protein and sugar, substances found to some degree in most foods, are heated up together. They undergo something called the Maillard reaction and N-glucosides are the result. N-glucosides themselves then undergo more reactions and become a multitude of flavour and colour compounds.

You know that lovely brown colour you get on cooked food – the colour of toast, or roast potatoes, or Christmas cake – that colour isn’t burning. It’s N-glucosides.

Technically, of course, N-glucoside isn’t a molecule but a class of molecules. It’s yet another of those situations where we name something after its primary functional group, and ignore the shrubbery. There are two ‘R’ groups in N-glucoside, which gives rise to a huge range of possibilities.

I can’t find a good picture of the functional group without shrubbery confusing the issue, so let’s do an exercise in visualisation. Take a carbon. Stick one H, one OH, one R and one NHR onto it. The N in C-NHR is three-cornered, having single bonds to H, R and C.

Got it?

Well done. That’s N-glucoside.


It’s been a joy to produce this calendar. I hope you’ve enjoyed the ride. I hope you’ve learned from it. I hope you feel more comfortable with the idea of chemistry, that Science is to some degree less daunting. Because if you’re still here, you can do this. Maybe you’re not a scientist of any stripe. Maybe you didn’t choose to study chemistry. But if you’ve read and understood all or some of this series of posts, understanding chemistry is not beyond you. You don’t have time to learn everything about everything – nobody does. But you know you could learn this, if you needed to.

I hope that feels good.

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