2012년 12월 24일 월요일

fischer projection


  • absolute configuration
    • absolute configuration
    • The chiral carbon furthest from the carbonyl group determines the absolute configuration L or D of the sugar.
    • If in the fischer projection, the OH group on the chiral carbon furthest from the carbonyl is pointing left, then it's L. If it's pointing right, then it's D.
    • Note: L and D are enantiomers, not epimers. So, every chiral carbon center inverts. It's just that you assign L and D based on the chiral carbon furthest from the carbonyl.
  • cyclic structure and conformations of hexoses
    • fructofuranose
    • Fructose forms a furanose when carbon 5 attacks the carbonyl carbon.
    • glucopyranose
    • Glucose forms a pyranose when carbon 5 attacks the carbonyl carbon.
    • Convert a Fischer projection to Haworth (cyclic) form
      • -OH groups that are pointing Left on the Fischer becomes Up on the Haworth.
      • -OH groups that are pointing Right on the Fischer becomes Down on the Haworth.
      • The -OH group on the anomeric carbon (the Fischer carbonyl) can be either up (beta) or down (alpha).
      • The CH2OH group on the absolute configuration carbon (carbon 5) points up for D, and down for L.

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