Chemistry / Organic Chemistry 9 / Chapter 24 / Problem 24

Organic Chemistry | 9th Edition | ISBN: 9781305080485 | Authors: John E. McMurry

Chlorophyll, heme, vitamin B12, and a host of other

Chapter 24, Problem 24

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Chlorophyll, heme, vitamin $B_{12}$, and a host of other substances are biosynthesized from porphobilinogen (PBG), which is itself formed from condensation of two molecules of 5-aminolevulinate. The two 5-amino levulinates are bound to lysine (Lys) amino acids in the enzyme, one in the enamine form and one in the imine form, and their condensation is thought to occur by the following steps. Using curved arrows, show the mechanism of each step.

Equation Transcription:

${B}_{12}$

$C{{O}_{2}}^{-}$

$N{H}_{2}$

$C{{O}_{2}}^{-}$

$N{H}_{2}$

$C{{O}_{2}}^{-}$

$N{H}_{2}$

$C{{O}_{2}}^{-}$

${H}_{2}N$

$C{{O}_{2}}^{-}$

$N{H}_{2}$

$C{{O}_{2}}^{-}$

$N{H}_{2}$

$C{{O}_{2}}^{-}$

$N{H}_{2}$

$C{{O}_{2}}^{-}$

$N{H}_{2}$

$C{{O}_{2}}^{-}$

$N{H}_{2}$

$C{{O}_{2}}^{-}$

Text Transcription:

B_12

CO_2-

NH_2

CO_2-

NH_2

CO_2-

NH_2

CO_2-

H_2N

CO_2-

NH_2

CO_2-

NH_2

CO_2-

NH_2

CO_2-

NH_2

CO_2-

NH_2

CO_2-

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