[Estana]

Hi,

I was just wondering if anyone could tell me which carbon atoms in a shikimic acid molecule are chiral, and why?

Thanks!

[Perito]

Unfortunately, you didn't draw a picture of Shikmic Acid, nor did you give me the formula. Since I've never heard of the stuff, I had to look it up on Wikipedia:

Shikimic acid - Wikipedia, the free encyclopedia

I also took the image from there. I've put "A", "B", and "C" on the diagram to show three carbons. These are the three chiral carbons.

The requirement for a carbon to be chiral is that all four groups attached to the carbon are different from each other.

Carbon A has an alcohol, a double-bonded carbon, another chiral carbon, and a hydrogen attached to it. These are all different. The same is true of carbons B and C. In the case of B, it's attached to two carbons that are similar, but the next groups are different. It's the "whole enchilada" that has to be different -- and they are.

[Estana]

Oh Im sorry, I apologise for not giving you the formula for it. I'm a Chemistry beginner and so thought (wrongly) that since what Ive been reading refers to it, it was common knowledge. Sorry again! And thank you very much for your explanation.