Lovastatin - chiral centres HELP! Watch

StephAmanda
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Report Thread starter 8 years ago
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Hey, can anybody tell me how many chiral centres the molecules lovastatin has? I can only find 2 but please explain to me how, if you find more.

Also i need to know how many stereoisomers the molecule has based on the chiral centres, i assume you just double the amount of chiral centres found.. is this true?

Also what functional groups in the molecule are prone to hydrolysis, the only ones i can think of are the two ester groups.

Thank you

heres is the link to the molecule:
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shengoc
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I see 8 chiral centres. bearing in mind that where you see the wedges drawn, if you can see 4 different groups projecting outwards from the same carbon centre - that is a chiral centre, and there are a few of these that you might have missed out.

Perhaps, you should refine what you actually understand of chirality.
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StephAmanda
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Thank you for your help, just found the 8 you specified. I originally understood it as just the groups directly attached not groups that were distantly attached if that makes sense.

So if there is 8 chiral centres, there is 16 stereoisomers?
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shengoc
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(Original post by StephAmanda)
Thank you for your help, just found the 8 you specified. I originally understood it as just the groups directly attached not groups that were distantly attached if that makes sense.

So if there is 8 chiral centres, there is 16 stereoisomers?
Not sure if you have heard of meso compounds before, ie due to the presence of internal symmetry plane, two molecules that you would think of as enantiomers are actually the same after you rotate them, so they are superimposable and hence cannot be chiral.

More to be found here,
http://en.wikipedia.org/wiki/Meso_compound

But from what i can see in this molecule, there isn't such symmetrical issue, so you'd expect potentially maximum of 2^8 = 256 stereoisomers, not 2*8!
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