uroporphyrinogen I shape.

[Whiteshoes]

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TBR had a question about being symmetric. I've spent like 5-10 minutes starring at the dumb thing and still don't see the symmetry. Can some explain where is the symmetry? Every where I draw an imaginary line (horizontal, vertical, diagonal) it doesn't fold up symmetrically. It's driving me nuts.

http://www.pearsonhighered.com/mathews/UV/UROPOR1.GIF

 

[MedPR]

Draw a horizontal line through the plane of the page and fold it inward on itself. It will superimpose.

 

[Whiteshoes]

Draw a horizontal line through the plane of the page and fold it inward on itself. It will superimpose.

If you do that then the 3 carbon carboxylic side chain gets matched up with the 2 carbon carboxylic side chain??

 

[ikjadoon]

Maybe it's symmetry in the same plane as the rings...so the symmetry goes through the atoms. It's like if you looked at a sheet of paper "thin side on" and then sliced that in half. Maybe like two-ply tissue paper when you split it?

It seems probable because it doesn't have any chiral carbons, so we don't have to worry about R/S matching up (as if we were going to classify it as meso or not). If it had chiral carbons, then this would not be possible. I'm not great at stereochemistry, though, so that might be wrong, lol.

 

[gentlebeast]

It has a inversion point in the middle. It is a mesocompound. Everything has inversion point is symmetric. I mean symmetric around a point not a plane here.

 

[Morsetlis]

Perhaps it's rotational symmetry, or perhaps the 3D shape is more symmetric than the plane shape.

Why does this matter? 😛