Question about D/L-glucose?

So, sugar in general. How do you know whether a ring-shaped sugar is D or L? And if it's rolled up into a circle, or vice versa, how do you know which side the OHs go on? I mean, if they were somewhere in the ring, how do you know whether they go on the left or right of the rolled-up molecule, and vice versa?

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ThomasJNewton
2 years ago

First of all, the ring closure does not alter the belonging to the D or L series. Rather (in the case of glucose) a fifth carbon atom becomes chiral, whose configuration is then referred to as α or β.
The difficulty lies in the spatial imagination. For open sugar is usually the fishing projection, for ring-shaped Hayworth projection. During the transition, the sugar is tipped to the right, therefore the rule FiSlaughterinks – Hayworth oben. It is, of course, difficult to imagine spatially without a molecular module.

In the case of an open single sugar, the affiliation of a row is determined by the “last” asymmetrical carbon atom, i.e. the one with the highest number. In the case of glucose, therefore, by C-5. The configuration of the other asymmetric C atoms results from the name, that is, for example, that the sugar is called galactose instead of glucose.

Is, of course, still a challenge to conclude from your picture in the Hayworth projection that the O-atom C-5 used for ring closure was originally right. It only helps practice, practice, practice.

Entomologist
2 years ago

The 1st C atom in which the alpha stands when the OH group points upwards it is L, and when the group points downwards D.

Entomologist
2 years ago

I have to correct myself. There’s a mistake in the rush. Shows the OH score at which the Alpha stands down, it is alpha. If she gets up, it’s Beta. Whether it’s D or L configuration, you can see the Ch2OH group on the 5th C atom. This is the blue-marked group that is in the top of the picture in the ring structure. Showing the up is D, showing it down is L. Sorry, I’m not an expert but I hope it’s right now.