FIGURE 29.4 MECHANISM -

The four steps of the $\boldsymbol{\beta}$-oxidation pathway, resulting in the cleavage of an acetyl group from the end of the fatty-acid chain. The key chain-shortening step is a retro-Claisen reaction of a $\beta$-keto thioester. Individual steps are explained in the text.
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Fatty acyl CoA
(1) A conjugated double bond is introduced by removal of hydrogens from C2 and C3 by the coenzyme flavin adenine
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$\alpha, \beta$-Unsaturated acyl CoA
(2) $\downarrow \mathrm{H}_{2} \mathrm{O}$ $\beta$-hydroxyacyl CoA.
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$\beta$-Hydroxyacyl CoA
(3) The alcohol is oxidized by $\mathrm{NAD}^{+}$to give a $\beta$-keto thioester.
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(4) Nucleophilic addition of coenzyme A to the keto group occurs, followed by a retro-Claisen condensation reaction. The products are acetyl CoA and a chain-shortened fatty acyl CoA.


FIGURE 29.4 MECHANISM -

Acetyl CoA


FIGURE 29.4 MECHANISM -

Step 1 of FIGURE 29.4: Introduction of a Double Bond
The $\beta$-oxidation pathway begins when two hydrogen atoms are removed from C 2 and C 3 of the fatty acyl CoA by one of a family of acyl-CoA dehydrogenases to yield an $\alpha, \beta$-unsaturated acyl CoA. This kind of oxidation-the introduction of a conjugated double bond into a carbonyl compound-occurs frequently in biochemical pathways and usually involves the coenzyme flavin adenine dinucleotide (FAD). Reduced $\mathrm{FADH}_{2}$ is the byproduct.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1045.jpg?height=936&width=1169&top_left_y=188&top_left_x=478)


FIGURE 29.4 MECHANISM -

The mechanisms of FAD-catalyzed reactions are often difficult to establish because flavin coenzymes can follow both two-electron (polar) and one-electron (radical) pathways. As a result, extensive studies of the family of acyl-CoA dehydrogenases have not yet provided a clear picture of how these enzymes function. What is known is that: (1) The first step is abstraction of the pro- $R$ hydrogen from the acidic $\alpha$ position of the acyl CoA to give a thioester enolate ion. Hydrogen-bonding between the acyl carbonyl group and the ribitol hydroxyls of FAD increases the acidity of the acyl group. (2) The pro- $R$ hydrogen at the $\beta$ position is transferred to FAD. (3) The $\alpha, \beta$-unsaturated acyl CoA that results has a trans double bond.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1045.jpg?height=350&width=1197&top_left_y=1446&top_left_x=464)


FIGURE 29.4 MECHANISM -

One suggested mechanism has the reaction taking place by a conjugate nucleophilic addition of hydride, analogous to what occurs during alcohol oxidations with $\mathrm{NAD}^{+}$. Electrons on the enolate ion might expel a $\beta$ hydride ion, which could add to the doubly bonded N5 nitrogen on FAD. Protonation of the intermediate at N1 would give the product.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1045.jpg?height=552&width=1060&top_left_y=1979&top_left_x=527)


FIGURE 29.4 MECHANISM -

Step 2 of FIGURE 29.4: Conjugate Addition of Water
The $\alpha, \beta$-unsaturated acyl CoA produced in step 1 reacts with water by a conjugate addition pathway (Section 19.13) to yield a $\beta$-hydroxyacyl CoA in a process catalyzed by enoyl CoA hydratase. Water as nucleophile adds to the $\beta$ carbon of the double bond, yielding an intermediate thioester enolate ion that is protonated on the $\alpha$ position.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1046.jpg?height=337&width=1055&top_left_y=433&top_left_x=508)
(3S)-Hydroxyacyl CoA
Step 3 of FIGURE 29.4: Alcohol Oxidation
The $\beta$-hydroxyacyl CoA from step 2 is oxidized to a $\beta$-ketoacyl CoA in a reaction catalyzed by one of a family of L-3-hydroxyacyl-CoA dehydrogenases, which differ in substrate specificity according to the chain length of the acyl group. As in the oxidation of $s n$-glycerol 3-phosphate to dihydroxyacetone phosphate mentioned at the end of Section 29.2, this alcohol oxidation requires $\mathrm{NAD}^{+}$as a coenzyme and yields reduced $\mathrm{NADH} / \mathrm{H}^{+}$as byproduct. Deprotonation of the hydroxyl group is carried out by a histidine residue at the active site.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1046.jpg?height=505&width=1261&top_left_y=1143&top_left_x=429)


Step 4 of FIGURE 29.4: Chain Cleavage -

Acetyl CoA is split off from the chain in the final step of $\beta$-oxidation, leaving an acyl CoA that is two carbon atoms shorter than the original. The reaction is catalyzed by $\beta$-ketoacyl-CoA thiolase and is mechanistically the reverse of a Claisen condensation reaction (Section 23.7). In the forward direction, a Claisen condensation joins two esters together to form a $\beta$-keto ester product. In the reverse direction, a retro-Claisen reaction splits apart a $\beta$-keto ester (or $\beta$-keto thioester in this case) to form two esters (or two thioesters).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1046.jpg?height=177&width=1237&top_left_y=1950&top_left_x=436)


Step 4 of FIGURE 29.4: Chain Cleavage -

The retro-Claisen reaction occurs by nucleophilic addition of a cysteine - SH group on the enzyme to the keto group of the $\beta$-ketoacyl CoA to yield an alkoxide ion intermediate. Cleavage of the $\mathrm{C} 2-\mathrm{C} 3$ bond then follows, with the expulsion of an acetyl CoA enolate ion that is immediately protonated. The enzyme-bound acyl group then undergoes nucleophilic acyl substitution by reaction with a molecule of coenzyme A, and the chain-shortened acyl CoA that results re-enters the $\beta$-oxidation pathway for further degradation.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1047.jpg?height=676&width=1592&top_left_y=188&top_left_x=264)


Step 4 of FIGURE 29.4: Chain Cleavage -

Look at the catabolism of myristic acid shown in FIGURE 29.5 to see the overall results of the $\beta$-oxidation pathway. The first passage converts the 14 -carbon myristoyl CoA into the 12 -carbon lauroyl CoA plus acetyl CoA, the second passage converts lauroyl CoA into the 10-carbon caproyl CoA plus acetyl CoA, the third passage converts caproyl CoA into the 8 -carbon capryloyl CoA, and so on. Note that the final passage produces two molecules of acetyl CoA because the precursor has four carbons.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1047.jpg?height=107&width=979&top_left_y=1096&top_left_x=416)


Step 4 of FIGURE 29.4: Chain Cleavage -

Myristoyl CoA


Step 4 of FIGURE 29.4: Chain Cleavage -

$$
\begin{aligned}
& \beta \text {-Oxidation } \\
& \text { (passage 1) }
\end{aligned}
$$


Step 4 of FIGURE 29.4: Chain Cleavage -


Step 4 of FIGURE 29.4: Chain Cleavage -

Lauroyl CoA
$\downarrow \begin{aligned} & \beta \text {-Oxidation } \\ & \text { (passage 2) }\end{aligned}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1047.jpg?height=96&width=922&top_left_y=1573&top_left_x=420)


Step 4 of FIGURE 29.4: Chain Cleavage -

Caproyl CoA


Step 4 of FIGURE 29.4: Chain Cleavage -

$$
\begin{aligned}
& \beta \text {-Oxidation } \\
& \text { (passage 3) }
\end{aligned}
$$


Capryloyl CoA -

FIGURE 29.5 Catabolism of the 14 -carbon myristic acid by the $\boldsymbol{\beta}$-oxidation pathway yields seven molecules of acetyl CoA after six passages.


Capryloyl CoA -

Most fatty acids have an even number of carbon atoms, so none are left over after $\beta$-oxidation. Those fatty acids with an odd number of carbon atoms yield the three-carbon propionyl CoA in the final $\beta$-oxidation. Propionyl CoA is then converted to succinate by a multistep radical pathway, and succinate enters the citric acid cycle (Section 29.7). Note that the three-carbon propionyl group should technically be called propanoyl, but biochemists generally use the nonsystematic name.


Capryloyl CoA -

PROBLEM Write the equations for the remaining passages of the $\beta$-oxidation pathway following those shown
29-2 in Figure 29.5.
PROBLEM How many molecules of acetyl CoA are produced by catabolism of the following fatty acids, and how 29-3 many passages of the $\beta$-oxidation pathway are needed?
(a) Palmitic acid, $\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{14} \mathrm{CO}_{2} \mathrm{H}$
(b) Arachidic acid, $\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{18} \mathrm{CO}_{2} \mathrm{H}$


Capryloyl CoA - 29.4 Biosynthesis of Fatty Acids

One of the most striking features of the common fatty acids is that they have an even number of carbon atoms (TABLE 27.1). This occurs because all fatty acids are derived biosynthetically from acetyl CoA by sequential addition of two-carbon units to a growing chain. The acetyl CoA, in turn, arises primarily from the metabolic breakdown of carbohydrates in the glycolysis pathway, which we'll see in Section 29.5. Thus, dietary carbohydrates consumed in excess of immediate energy needs are turned into fats for storage.


As a general rule in biological chemistry, the anabolic pathway by which a substance is made is not the reverse of the catabolic pathway by which the same substance is degraded. The two paths must differ in some respects for both to be energetically favorable. Thus, the $\beta$-oxidation pathway for converting fatty acids into acetyl CoA and the biosynthesis of fatty acids from acetyl CoA are related but are not exact opposites. Differences include the identity of the acyl-group carrier, the stereochemistry of the $\beta$-hydroxyacyl reaction intermediate, and the identity of the redox coenzyme. FAD is used to introduce a double bond in $\beta$-oxidation, while NADPH is used to reduce the double bond in fatty-acid biosynthesis.


In bacteria, each step in fatty-acid synthesis is catalyzed by a separate enzyme. In vertebrates, however, fattyacid synthesis is catalyzed by an immense, multienzyme complex called a synthase that contains two identical subunits of 2505 amino acids each and catalyzes all steps in the pathway. In fact, for an 18-carbon fatty acid, the synthase catalyzes 42 separate steps! An overview of fatty-acid biosynthesis is shown in FIGURE 29.6.


Steps 1-2 of FIGURE 29.6: Acyl Transfers -

The starting material for fatty-acid biosynthesis is the thioester acetyl CoA, the final product of carbohydrate breakdown, as we'll see in Section 29.6. The pathway begins with several priming reactions, which transport acetyl CoA and convert it into more reactive species. The first priming reaction is a nucleophilic acyl substitution reaction that converts acetyl CoA into acetyl ACP (acyl carrier protein).


Notice that the mechanism of the nucleophilic acyl substitution in step 1 can be given in an abbreviated form that saves space by not explicitly showing the tetrahedral reaction intermediate. Instead, electron movement is shown as a heart-shaped path around the carbonyl oxygen to imply the two steps of the full mechanism. Biochemists commonly use this kind of abbreviated format, and we'll also use it on occasion through the rest of this chapter.


FIGURE 29.6 MECHANISM -

The pathway for fatty-acid biosynthesis from the two-carbon precursor, acetyl CoA. Individual steps are explained in the text.


FIGURE 29.6 MECHANISM -


(7) -

(5) Claisen-like condensation of malonyl ACP with acetyl synthase occurs, followed by decarboxylation to yield acetoacetyl ACP, a $\beta$-keto thioester.
(6) Reduction of the ketone by NADPH yields the corresponding $\beta$-hydroxy thioester.


(7) -

Dehydration of $\beta$-hydroxybutyryl ACP gives crotonyl ACP, an $a, b$-unsaturated thioester.


(7) -

8 Reduction of the double bond yields the saturated, chain-elongated butyryl ACP.


Acetyl synthase -


Acetyl synthase -

Acetyl CoA
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1049.jpg?height=147&width=559&top_left_y=569&top_left_x=794)
(3) Acetyl CoA is carboxylated to give malonyl CoA.
(4) The malonyl group is transferred from CoA to ACP.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1049.jpg?height=111&width=233&top_left_y=1256&top_left_x=954)


Acetyl synthase -

Butyryl ACP
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1050.jpg?height=310&width=998&top_left_y=189&top_left_x=561)


Acetyl synthase -

Tetrahedral intermediate
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1050.jpg?height=345&width=863&top_left_y=603&top_left_x=631)


Acetyl synthase -

In bacteria, ACP is a small protein of 77 residues that transports an acyl group from one enzyme to another. In vertebrates, however, ACP appears to be a long arm on a multienzyme synthase complex, whose apparent function is to shepherd an acyl group from site to site within the complex. As in acetyl CoA, the acyl group in acetyl ACP is linked by a thioester bond to the sulfur atom of phosphopantetheine. The phosphopantetheine is in turn linked to ACP through the side-chain -OH group of a serine residue in the enzyme.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1050.jpg?height=247&width=896&top_left_y=1183&top_left_x=612)


Acetyl ACP -

Step 2, another priming reaction, involves a further exchange of thioester linkages by another nucleophilic acyl substitution and results in covalent bonding of the acetyl group to a cysteine residue in the synthase complex that catalyzes the upcoming condensation step.


Acetyl ACP -

Steps 3-4 of FIGURE 29.6: Carboxylation and Acyl Transfer
Step 3 is a loading reaction in which acetyl CoA is carboxylated by reaction with $\mathrm{HCO}_{3}{ }^{-}$and ATP to yield malonyl CoA plus ADP. This step requires the coenzyme biotin, which is bonded to the lysine residue of acetyl CoA carboxylase and acts as a carrier of $\mathrm{CO}_{2}$. Biotin first reacts with bicarbonate ion to give $N$-carboxybiotin, which then reacts with the enolate ion of acetyl CoA and transfers the $\mathrm{CO}_{2}$ group. Thus, biotin acts as a carrier of $\mathrm{CO}_{2}$, binding it in one step and releasing it in another.

The mechanism of the $\mathrm{CO}_{2}$ transfer reaction with acetyl CoA to give malonyl CoA is thought to involve $\mathrm{CO}_{2}$ as the reactive species. One proposal is that the loss of $\mathrm{CO}_{2}$ is favored by hydrogen-bond formation between the N -carboxybiotin carbonyl group and a nearby acidic site in the enzyme. Simultaneous deprotonation of acetyl CoA by a basic site in the enzyme gives a thioester enolate ion that can react with $\mathrm{CO}_{2}$ as it forms (FIGURE 29.7).


FIGURE 29.7 MECHANISM -


Mechanism of step 3 in FIGURE 29.6, the biotin-dependent carboxylation of acetyl CoA to yield malonyl -


Malonyl CoA


Following the formation of malonyl CoA, another nucleophilic acyl substitution reaction occurs in step 4 to form the more reactive malonyl ACP, thereby binding the malonyl group to an ACP arm of the multienzyme synthase. At this point, both acetyl and malonyl groups are bound to the enzyme, and the stage is set for their condensation.


Step 5 of FIGURE 29.6: Condensation -

The key carbon-carbon bond-forming reaction that builds the fatty-acid chain occurs in step 5 . This step is simply a Claisen condensation between acetyl synthase as the electrophilic acceptor and malonyl ACP as the nucleophilic donor. The mechanism of the condensation is thought to involve decarboxylation of malonyl ACP to give an enolate ion, followed by immediate nucleophilic addition of the enolate ion to the carbonyl group of acetyl synthase. Breakdown of the tetrahedral intermediate then gives the four-carbon condensation product acetoacetyl ACP and frees the synthase binding site for attachment of the chain-elongated acyl group at the end of the sequence.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1052.jpg?height=457&width=1441&top_left_y=189&top_left_x=342)


Step 5 of FIGURE 29.6: Condensation -

Steps 6-8 of FIGURE 29.6: Reduction and Dehydration
The ketone carbonyl group in acetoacetyl ACP is next reduced to the alcohol $\beta$-hydroxybutyryl ACP by $\beta$-keto thioester reductase and NADPH, a reducing coenzyme closely related to NADH. $R$ stereochemistry results at the newly formed chirality center in the $\beta$-hydroxy thioester product. (Note that the systematic name of a butyryl group is butanoyl.)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1052.jpg?height=370&width=1349&top_left_y=902&top_left_x=388)

Subsequent dehydration of $\beta$-hydroxybutyryl ACP by an E1cB reaction in step 7 yields trans-crotonyl ACP, and the carbon-carbon double bond of crotonyl ACP is reduced by NADPH in step 8 to yield butyryl ACP. The doublebond reduction occurs by conjugate nucleophilic addition of a hydride ion from NADPH to the $\beta$ carbon of trans-crotonyl ACP. In vertebrates, this reduction occurs by an overall syn addition, but other organisms carry out similar chemistry with different stereochemistry.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1052.jpg?height=508&width=1082&top_left_y=1508&top_left_x=516)


Step 5 of FIGURE 29.6: Condensation -

The net effect of the eight steps in the fatty-acid biosynthesis pathway is to take two 2 -carbon acetyl groups and combine them into a 4-carbon butyryl group. Further condensation of the butyryl group with another malonyl ACP yields a 6-carbon unit, and still further repetitions add two carbon atoms at a time until the 16-carbon palmitoyl ACP is produced.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1052.jpg?height=139&width=1459&top_left_y=2207&top_left_x=333)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1052.jpg?height=99&width=993&top_left_y=2360&top_left_x=558)


Step 5 of FIGURE 29.6: Condensation -

Palmitoyl ACP


Step 5 of FIGURE 29.6: Condensation -

Further chain elongation of palmitic acid occurs by reactions similar to those just described, but CoA rather than ACP acts as the carrier group, and separate enzymes are needed for each step rather than a multienzyme synthase complex.


Step 5 of FIGURE 29.6: Condensation -

PROBLEM Write a mechanism for the dehydration reaction of $\beta$-hydroxybutyryl ACP to yield crotonyl ACP in 29-4 step 7 of fatty-acid synthesis.


Step 5 of FIGURE 29.6: Condensation -

PROBLEM Evidence for the role of acetate in fatty-acid biosynthesis comes from isotope-labeling experiments.
29-5 If acetate labeled with ${ }^{13} \mathrm{C}$ in the methyl group $\left({ }^{13} \mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\right)$ were incorporated into fatty acids, at what positions in the fatty-acid chain would you expect the ${ }^{13} \mathrm{C}$ label to appear?


Step 5 of FIGURE 29.6: Condensation -

PROBLEM Does the reduction of acetoacetyl ACP in step 6 occur on the Re face or the Si face of the molecule? 29-6
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1053.jpg?height=248&width=911&top_left_y=662&top_left_x=409)


Step 5 of FIGURE 29.6: Condensation - 29.5 Catabolism of Carbohydrates: Glycolysis

Glucose is the body's primary short-term energy source. Its catabolism begins with glycolysis, a series of ten enzyme-catalyzed reactions that break down glucose into 2 equivalents of pyruvate, $\mathrm{CH}_{3} \mathrm{COCO}_{2}{ }^{-}$. The steps of glycolysis, also called the Embden-Meyerhoff pathway after its discoverers, are summarized in FIGURE 29.8.


The ten-step glycolysis pathway for catabolizing glucose to two molecules of pyruvate. Individual steps are described in the text.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1054.jpg?height=202&width=508&top_left_y=425&top_left_x=830)
(1) Glucose is phosphorylated by reaction with ATP to yield glucose 6-phosphate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1054.jpg?height=117&width=163&top_left_y=646&top_left_x=1141)
$\alpha$-Glucose 6-phosphate
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Glucose 6-phosphate is isomerized to fructose 6-phosphate by ring opening followed by a keto-enol tautomerization.
(2)


$\alpha$-Fructose 6-phosphate -


$\alpha$-Fructose 6-phosphate -

Fructose 6-phosphate is phosphorylated by reaction with ATP to yield fructose
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1054.jpg?height=117&width=155&top_left_y=1324&top_left_x=1142)


$\alpha$-Fructose 6-phosphate -

1,6-bisphosphate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1054.jpg?height=126&width=299&top_left_y=1319&top_left_x=1019)
$\beta$-Fructose 1,6-bisphosphate
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1054.jpg?height=218&width=426&top_left_y=1444&top_left_x=985)
(4) Fructose 1,6-bisphosphate undergoes ring opening and is cleaved by a retro-aldol reaction into glyceraldehyde 3-phosphate and dihydroxyacetone phosphate (DHAP).
(5) DHAP then isomerizes to glyceraldehyde 3-phosphate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1054.jpg?height=201&width=1254&top_left_y=1924&top_left_x=449)


FIGURE 29.9 MECHANISM -


(Continued) -


Glyceraldehyde 3-phosphate -

6) Glyceraldehyde 3-phosphate is oxidized to a carboxylic acid and then phosphorylated to yield 1,3-bisphosphoglycerate.
$6 \curvearrowleft \mathrm{NAD}^{+}, \mathrm{P}_{\mathrm{i}}$


Glyceraldehyde 3-phosphate -

1,3-Bisphosphoglycerate ${ }^{2-} \mathrm{O}_{3} \mathrm{POCH}_{2} \mathrm{CHCO}_{2} \mathrm{PO}_{3}{ }^{2-}$
(7) A phosphate is transferred from the carboxyl group to ADP, resulting in synthesis of an ATP and yielding 3-phosphoglycerate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1055.jpg?height=135&width=172&top_left_y=751&top_left_x=1101)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1055.jpg?height=205&width=264&top_left_y=716&top_left_x=1413)


Glyceraldehyde 3-phosphate -

3-Phosphoglycerate
8 Isomerization of 3-phosphoglycerate gives 2-phosphoglycerate.


Glyceraldehyde 3-phosphate -

2-Phosphoglycerate
9 Dehydration occurs to yield phosphoenolpyruvate (PEP).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1055.jpg?height=102&width=172&top_left_y=1277&top_left_x=1096)


Glyceraldehyde 3-phosphate -


Glyceraldehyde 3-phosphate -

Steps 1-2 of FIGURE 29.8: Phosphorylation and Isomerization
Glucose, produced by the digestion of dietary carbohydrates, is phosphorylated at the C6 hydroxyl group by reaction with ATP in a process catalyzed by hexokinase. As noted in Section 29.1, the reaction requires $\mathrm{Mg}^{2+}$ as a cofactor to complex with the negatively charged phosphate oxygens. The glucose 6-phosphate that results is then isomerized by glucose 6-phosphate isomerase to give fructose 6-phosphate. This isomerization takes place by initial opening of the glucose hemiacetal ring to its open-chain form, followed by keto-enol tautomerization to a cis enediol, $\mathrm{HO}-\mathrm{C}=\mathrm{C}-\mathrm{OH}$. But because glucose and fructose share a common enediol, further tautomerization to a different keto form produces open-chain fructose, and cyclization completes the process (FIGURE 29.10).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1056.jpg?height=403&width=605&top_left_y=338&top_left_x=348)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1056.jpg?height=335&width=865&top_left_y=762&top_left_x=348)
$\alpha$-Fructose
6-phosphate

FIGURE 29.10 Mechanism of step 2 in glycolysis, the isomerization of glucose 6-phosphate to fructose 6-phosphate.
Step 3 of FIGURE 29.8: Phosphorylation
Fructose 6-phosphate is converted in step 3 to fructose 1,6-bisphosphate (FBP) by a phosphofructokinasecatalyzed reaction with ATP (recall that the prefix bis- means two). The mechanism is similar to that in step 1 , with $\mathrm{Mg}^{2+}$ ion again required as cofactor. Interestingly, the product of step 2 is the $\alpha$ anomer of fructose 6-phosphate, but it is the $\beta$ anomer that is phosphorylated in step 3 , implying that the two anomers equilibrate rapidly through the open-chain form. The result is a molecule ready to be split into the two three-carbon intermediates that will ultimately become two molecules of pyruvate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1056.jpg?height=372&width=1434&top_left_y=1565&top_left_x=340)

Step 4 of FIGURE 29.8: Cleavage
Fructose 1,6-bisphosphate is cleaved in step 4 into two 3-carbon pieces, dihydroxyacetone phosphate (DHAP) and glyceraldehyde 3-phosphate (GAP). The bond between C3 and C4 of fructose 1,6-bisphosphate breaks, and a $\mathrm{C}=\mathrm{O}$ group is formed at C 4 . Mechanistically, the cleavage is the reverse of an aldol reaction (Section 23.1) and is catalyzed by an aldolase. A forward aldol reaction joins two aldehydes or ketones to give a $\beta$-hydroxy carbonyl compound, while a retro-aldol reaction, as in this case, cleaves a $\beta$-hydroxy carbonyl compound into two aldehydes or ketones.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1057.jpg?height=518&width=1175&top_left_y=180&top_left_x=475)


Glyceraldehyde 3-phosphate -

Two classes of aldolases are used by organisms for catalysis of the retro-aldol reaction. In fungi, algae, and some bacteria, the retro-aldol reaction is catalyzed by class II aldolases, which function by coordination of the fructose carbonyl group with $\mathrm{Zn}^{2+}$ as Lewis acid. In plants and animals, the reaction is catalyzed by class I aldolases and does not take place on the free ketone. Instead, fructose 1,6 -bisphosphate undergoes reaction with the side-chain $-\mathrm{NH}_{2}$ group of a lysine residue on the aldolase to yield a protonated enzyme-bound imine (Section 19.8), which is often called a Schiff base in biochemistry.


Glyceraldehyde 3-phosphate -

Because of its positive charge, the iminium ion is a better electron acceptor than a ketone carbonyl group. Retroaldol reaction ensues, giving glyceraldehyde 3-phosphate and an enamine, which is protonated to give another iminium ion that is hydrolyzed to yield dihydroxyacetone phosphate (FIGURE 29.11).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1057.jpg?height=936&width=1380&top_left_y=1126&top_left_x=367)