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Ribose cyclization: pyrane or furane?

  1. Aug 26, 2012 #1

    Aymeric

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    Hello,

    My biochemistry textbook tells me that ribose and fructose give furanes. I had trouble wrapping my head around the cyclization process so I looked for other explanations and I found this one:
    http://web.campbell.edu/faculty/nemecz/323_lect/sugars/cyclization.html [Broken]

    It seems to say that ribose can take on two forms : furane or pyrane. I just wanted confirmation that linear ribose becomes a furane or a pyrane depending on which -OH connects back to the aldehyde function (if it connects to the last one, it becomes ribopyranose, if it connects to the one before last, it becomes ribofuranose).

    Did I get this right?

    Thanks!
     
    Last edited by a moderator: May 6, 2017
    Aymeric, Aug 26, 2012
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  3. Aug 26, 2012 #2

    chemisttree

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    Sounds right to me. Intramolecular aldol condensation.

    edit: But you will get both the alpha and beta anomer for both of these cyclic forms depending upon which 'face' of the aldehyde the OH approaches.
     
    Last edited: Aug 27, 2012
    chemisttree, Aug 26, 2012
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