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Topic: Need help with an interesting Bioorganic Chem question  (Read 1587 times)

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Offline 2xmajor2xwork

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Need help with an interesting Bioorganic Chem question
« on: February 08, 2014, 08:36:52 PM »
Hello everyone, this is my first post so I hope I format everything correctly and all that jazz.

I am working through a problem set on carbohydrates and hit a rather vague and interesting question. It is dealing with the structure and stereocenters of mono-saccharides. The question is as follows : What can decrease the maximum number of possible stereocenters?

I believe I might be over thinking this one a little, but my best attempt at an answer would be the bonding of a like functional group to one of the chiral centers.

Does this sound correct, or is there something I may be missing?

Thanks for your help.

Offline PhDoc

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Re: Need help with an interesting Bioorganic Chem question
« Reply #1 on: February 09, 2014, 12:43:01 PM »
When you submit a question like this, it's best to include the structure. Not including the structure is like asking the question, "What flavor is it?" when there is nothing in perspective.

So, let's focus on glucose. What can you do to it to decrease the maximum number of stereocenters? What chemistry do you know that can do this?

P.S. I'd be very likely to put a problem like this on an exam because it requires thought, not memorization.
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Offline 2xmajor2xwork

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Re: Need help with an interesting Bioorganic Chem question
« Reply #2 on: February 09, 2014, 01:07:57 PM »
I'm sorry, on this problem set there were no structures shown, or even mentioned. I believe he is going for more of the learning than memorizing, as you said. Would tautomerization be a possible way to decrease the number of stereocenters?

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