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Lecture 5

Chemistry 2223B Lecture Notes - Lecture 5: Pyruvate Dehydrogenase Complex, Phosphoglycerate Mutase, Phosphoglycerate Kinase


Department
Chemistry
Course Code
CHEM 2223B
Professor
Len Luyt
Lecture
5

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Carbohydrates 60
d. Aldolase (fructose-1,6-bisphosphate
DHAP and G-3-P)
We have previously seen the mechanism of aldolase. In the forward direction, two
C3 compounds are joined to produce a -hydroxy carbonyl compound. A retro-aldol
reaction is the reverse reaction.
CH2OPO32-
O
CH2OH
H OH
OH
CH2OPO32-
H OH
OH
CH2OPO32-
HO H
CH2OPO32-
O
H
CH2OPO32-
O
CHOH
H
In the above reaction, the C=O is the electron acceptor. This is the case for simple
organisms, such as fungi and bacteria, but in plants and animals, the aldolase
enzyme is more efficient and takes a modified route by using a positively charged
nitrogen as the electron acceptor.

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Carbohydrates 61
This is accomplished by forming an iminium ion (Schiff base) with a lysine side chain
(recall the reactions of aldehydes and ketones with amines to form imines).
CH2OPO32-
O
CH2OH
H OH
OH
CH2OPO32-
H OH
OH
CH2OPO32-
HO H
CH2OPO32-
O
H
CH2OPO32-
NH-Enz
CHOH
Enz-NH2
H OH
OH
CH2OPO32-
HO H
CH2OPO32-
NH-Enz
H
CH2OPO32-
NH-Enz
CH2OH
H2O

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Carbohydrates 62
e. Triosephosphate isomerase (dihydroxyacetone phosphate
G-3-P)
Homework: propose a mechanism for the following reaction:
CH2OPO32-
O
CH2OH
HOH
OH
CH2OPO32-
CH2OPO32-
O
CH2OH
C3 of DHAP came from C3 of glucose, which
turns into C1 of G-3-P and then C1 of pyruvate
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