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Topic: Stereochemistry  (Read 1961 times)

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Offline Monium101

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Stereochemistry
« on: July 06, 2014, 08:24:35 PM »
I'm having a rather difficult time grasping the concept of drawing pairs of entantiomers and pairs of disastereromers, so example how would I go about drawing these components for an amino acid such as leucine. I know first we can draw the diagram firsthand and label each wedge with the atoms and then we label them from 1-4  typically one has the highest priority since the atom there would have a greater atomic number and then go from there but after this point, everything else is a bit confusing. Can someone break it down for me in terms of labeling the structures first and arranging them please? Thanks in advance! :)

Offline discodermolide

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Re: Stereochemistry
« Reply #1 on: July 06, 2014, 08:33:31 PM »
Look up the definition of enantiomers and diastereoisomers.
Then search for the Cahn-Ingold-Prelog system of assigning (R) and (S) to the chiral carbon atoms.
From your question I think this is what you are  getting at.
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Offline Monium101

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Re: Stereochemistry
« Reply #2 on: July 06, 2014, 08:48:46 PM »
okay, once I have assigned R and S configurations on the chiral atoms how would I interpret the fact that diastereroisomers are basically stereoisomers that are not entantiomers into drawing them, im still a bit confused.

Offline discodermolide

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Re: Stereochemistry
« Reply #3 on: July 07, 2014, 12:08:21 AM »
You use the same method:
C[C@@H](O)C(O)CC
where the undefined C-OH is a mixture of enantiomers. This compound is a diastereoisomer.
So the two chiral diastereoisomers are:
C[C@@H](O)[C@H](O)CC
and
C[C@@H](O)[C@@H](O)CC

Note here the Smiles engine has labelled the molecules chiral and are not quite the same as I drew them. But it is correct.
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