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Question: Sugar Ring Cyclization

Started by churroes
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churroes

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Hi all,
I know from biochem that sugars like to cyclize as either furanose or pyranose.
Furanose can be formed by a C-4's OH onto C-1 attack on an 5 carbon aldose, or a C-5's OH to C-2 attack on a 6 carbon ketose.

Pyranose can be formed by a C-5's OH onto C-1 attack for a 6C aldose, or a C-6's OH to C-2 attack on a 7 carbon ketose.


My question is:
Why can't the terminal carbon's hydroxyl group attack to form a ring?
For an example using a 5-C aldose, why couldn't the C5 hydroxyl group attack the C1, forming a pyranose?


Thank you!
 
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