Skip to main content
Chemistry LibreTexts

14.S: The Oganic Chemistry of Vitamins (Summary)

  • Page ID
    242338
  • \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \)

    \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)

    \( \newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\)

    ( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\)

    \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\)

    \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\)

    \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\)

    \( \newcommand{\Span}{\mathrm{span}}\)

    \( \newcommand{\id}{\mathrm{id}}\)

    \( \newcommand{\Span}{\mathrm{span}}\)

    \( \newcommand{\kernel}{\mathrm{null}\,}\)

    \( \newcommand{\range}{\mathrm{range}\,}\)

    \( \newcommand{\RealPart}{\mathrm{Re}}\)

    \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\)

    \( \newcommand{\Argument}{\mathrm{Arg}}\)

    \( \newcommand{\norm}[1]{\| #1 \|}\)

    \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\)

    \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\AA}{\unicode[.8,0]{x212B}}\)

    \( \newcommand{\vectorA}[1]{\vec{#1}}      % arrow\)

    \( \newcommand{\vectorAt}[1]{\vec{\text{#1}}}      % arrow\)

    \( \newcommand{\vectorB}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \)

    \( \newcommand{\vectorC}[1]{\textbf{#1}} \)

    \( \newcommand{\vectorD}[1]{\overrightarrow{#1}} \)

    \( \newcommand{\vectorDt}[1]{\overrightarrow{\text{#1}}} \)

    \( \newcommand{\vectE}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{\mathbf {#1}}}} \)

    \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \)

    \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)

    After completing this chapter, you should be able to:

    • Understand how pyridoxal phosphate (PLP) acts as an 'electron sink' in a variety of reactions in amino acid metabolism.
    • Recognize and draw mechanisms for PLP-dependent transformations of the following types:
      • racemization
      • decarboxylation
      • transamination
      • retroaldol cleavage
      • retro-Claisen cleavage
      • \(\beta \)-elimination
      • \(\beta \)-substitution
      • \(\gamma \)-elimination
      • \(\gamma \)-substitution
    • Recognize transformations - amino acid decarboxylation and transamination, for example - in which chemical steps occur that simply don't 'make sense' unless the electron sink role of PLP is taken into account.
    • Understand how the orientation of the substrate in relation to the plane formed by the conjugated \(\pi \) system of PLP is a major factor in catalysis of PLP-dependent reactions.
    • Understand how thiamine diphosphate (\(ThDP\)) acts as an 'electron sink' in a variety of reactions in which a bond to a carbonyl carbon is broken, and how these steps do not 'make sense' unless the electron sink role of \(ThDP\) is taken into account.
    • Recognize transformations for which \(ThDP\) is likely required, and be able to draw reasonable mechanisms for them.
    • Understand how \(ThDP\) acts in tandem with lipoamide, flavin, and nicotinamide in the reaction catalyzed by pyruvate dehydrogenase.
    • Recognize folate in its various forms - \(DHF\), \(THF\), \(f-THF\), \(CH_2-THF\), and \(CH_3-THF\) - functions in a variety of one-carbon transfer steps. Be able to recognize the oxidation state of the carbon being transferred in a folate-depenent step.

    This page titled 14.S: The Oganic Chemistry of Vitamins (Summary) is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by Tim Soderberg.

    • Was this article helpful?