biochemmathecon
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hey can someone please help - I need mechanisms to show how manufacturers of a drug ensures they only produce 1 enantiomer (otherwise known as Enantioselective synthesis I THINK) so could someone pls help I can't find it online (I'm studying level chem) and could someone pls dumb down how this wouldn't work for the thalidomide drug?
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alow
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(Original post by biochemmathecon)
hey can someone please help - I need mechanisms to show how manufacturers of a drug ensures they only produce 1 enantiomer (otherwise known as Enantioselective synthesis I THINK) so could someone pls help I can't find it online (I'm studying level chem) and could someone pls dumb down how this wouldn't work for the thalidomide drug?
Enzymes are pretty good at it.

Thalidomide will racemise in vivo.
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Technetium
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I'm going to assume that you are familiar with the key terms such as chiral, enantiomer, etc. If not, you should learn and understand what they mean.

The synthesis of Thalidomide produced a racemic mixture of (R) and (S) enantiomers: one caused birth defects in newborn babies (teratogenic)(-S) and the other possessed the desired therapeutic effect (+R). The racemic mixture was a result of a chiral carbon atom in the chemical structure of Thalidomide, which gave rise to two possible arrangements of the atoms and thus, two enantiomers. Thalidomide was commercially available as a racemic mixture because the negative effects of the (-S) enantiomer were not known initially. The useful (+R) enantiomer was found to interconvert into the teratogenic (-S) enantiomer and thus, it was not possible to isolate it and sell it on its own.

There are numerous strategies used in industry to synthesise drugs enantioselectively, these range from employing chiral auxiliaries to organometallic catalysts to ensure that the desired enantiomer is produced in excess. However, these mechanisms are beyond the scope of an A-Level syllabus but you can read more about them here.
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biochemmathecon
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(Original post by Technetium)
I'm going to assume that you are familiar with the key terms such as chiral, enantiomer, etc. If not, you should learn and understand what they mean.

The synthesis of Thalidomide produced a racemic mixture of (R) and (S) enantiomers: one caused birth defects in newborn babies (teratogenic)(-S) and the other possessed the desired therapeutic effect (+R). The racemic mixture was a result of a chiral carbon atom in the chemical structure of Thalidomide, which gave rise to two possible arrangements of the atoms and thus, two enantiomers. Thalidomide was commercially available as a racemic mixture because the negative effects of the (-S) enantiomer were not known initially. The useful (+R) enantiomer was found to interconvert into the teratogenic (-S) enantiomer and thus, it was not possible to isolate it and sell it on its own.

There are numerous strategies used in industry to synthesise drugs enantioselectively, these range from employing chiral auxiliaries to organometallic catalysts to ensure that the desired enantiomer is produced in excess. However, these mechanisms are beyond the scope of an A-Level syllabus but you can read more about them here.
yes I am, and I am aware this is beyond alevel required content but its our summer work THANK YOU SO MUCH XX the link doesn't lead to a page though.
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Technetium
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(Original post by biochemmathecon)
yes I am, and I am aware this is beyond alevel required content but its our summer work THANK YOU SO MUCH XX the link doesn't lead to a page though.
No worries.

That's strange. When I click, it takes me to a Wikipedia page:

https://en.m.wikipedia.org/wiki/Enan...tive_synthesis

Enjoy!
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