The citric acid cycle is an eight-step series of reactions that results in the conversion of an acetyl group into two molecules of $\mathbf{C O}_{2}$ plus reduced coenzymes. Individual steps are explained in the text.
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Oxaloacetate
8 Oxidation of (S)-malate gives oxaloacetate, completing the cycle.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1065.jpg?height=123&width=272&top_left_y=1006&top_left_x=655)
(S)-Malate
(L-malate)
(7) Fumarate undergoes conjugate addition of water to its double bond to give (S)-malate.
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Fumarate
(6) Succinate is dehydrogenated by FAD to give fumarate.
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FIGURE 29.13 MECHANISM - 29.7 The Citric Acid Cycle

Citrate
2


Succinate
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1065.jpg?height=121&width=525&top_left_y=1788&top_left_x=949)


Succinyl CoA
Succinyl CoA is converted to
succinate in a reaction coupled to the phosphorylation of GDP to give GTP.


Step 1 of FIGURE 29.14: Addition to Oxaloacetate
Acetyl CoA enters the citric acid cycle in step 1 by nucleophilic addition to the oxaloacetate carbonyl group, to give (S)-citryl CoA. This addition is an aldol reaction and is catalyzed by citrate synthase, as discussed in Section 26.11. (S)-Citryl CoA is then hydrolyzed to citrate by a typical nucleophilic acyl substitution reaction with water, catalyzed by the same citrate synthase enzyme.


Note that the hydroxyl-bearing carbon of citrate is a prochirality center and contains two identical arms. Because the initial aldol reaction of acetyl CoA to oxaloacetate occurs specifically from the Si face of the
ketone carbonyl group, the pro- $S$ arm of citrate is derived from acetyl CoA and the pro- $R$ arm is derived from oxaloacetate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1066.jpg?height=629&width=1364&top_left_y=298&top_left_x=378)


Citrate
Step 2 of FIGURE 29.14: Isomerization
Citrate, a prochiral tertiary alcohol, is next converted into its isomer, ( $2 R, 3 S$ )-isocitrate, a chiral secondary alcohol. The isomerization occurs in two steps, both of which are catalyzed by the same aconitase enzyme. The initial step is an E1cB dehydration of a $\beta$-hydroxy acid to give cis-aconitate, the same sort of reaction that occurs in step 9 of glycolysis (FIGURE 29.8). The second step is a conjugate nucleophilic addition of water to the $\mathrm{C}=\mathrm{C}$ bond (Section 19.13). The dehydration of citrate takes place specifically on the pro- $R$ arm-the one derived from oxaloacetate-rather than on the pro- $S$ arm derived from acetyl CoA.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1066.jpg?height=307&width=1254&top_left_y=1343&top_left_x=430)

Step 3 of FIGURE 29.14: Oxidation and Decarboxylation
( $2 R, 3 S$ )-Isocitrate, a secondary alcohol, is oxidized by $\mathrm{NAD}^{+}$in step 3 to give the ketone oxalosuccinate, which loses $\mathrm{CO}_{2}$ to give $\alpha$-ketoglutarate. Catalyzed by isocitrate dehydrogenase, the decarboxylation is a typical reaction of a $\beta$-keto acid, just like that in the acetoacetic ester synthesis (Section 22.7). The enzyme requires a divalent cation as a cofactor to polarize the ketone carbonyl group and make it a better electron acceptor.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1066.jpg?height=539&width=1434&top_left_y=1915&top_left_x=343)


Step 4 of FIGURE 29.14: Oxidative Decarboxylation
The transformation of $\alpha$-ketoglutarate to succinyl CoA in step 4 is a multistep process just like the transformation of pyruvate to acetyl CoA that we saw in FIGURE 29.13. In both cases, an $\alpha$-keto acid loses $\mathrm{CO}_{2}$ and is oxidized to a thioester in a series of steps catalyzed by a multienzyme dehydrogenase complex. As in the conversion of pyruvate to acetyl CoA, the reaction involves an initial nucleophilic addition reaction of thiamin diphosphate ylide to $\alpha$-ketoglutarate, followed by decarboxylation. Reaction with lipoamide, elimination of TPP ylide, and finally a transesterification of the dihydrolipoamide thioester with coenzyme A yields succinyl CoA.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1067.jpg?height=229&width=945&top_left_y=533&top_left_x=590)


Step 5 of FIGURE 29.14: Acyl CoA Cleavage
Succinyl CoA is converted to succinate in step 5. This reaction is catalyzed by succinyl CoA synthetase and is coupled with phosphorylation of guanosine diphosphate (GDP) to give guanosine triphosphate (GTP). The overall transformation is similar to that of steps 6 through 8 in glycolysis (FIGURE 29.8), in which a thioester is converted into an acyl phosphate and a phosphate group is then transferred to ADP. The overall result is a "hydrolysis" of the thioester group without involvement of water.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1067.jpg?height=665&width=1429&top_left_y=1066&top_left_x=345)


Step 6 of FIGURE 29.14: Dehydrogenation
Succinate is dehydrogenated in step 6 by the FAD-dependent succinate dehydrogenase to give fumarate. This process is analogous to what occurs during the $\beta$-oxidation pathway of fatty-acid catabolism (Section 29.3). The reaction is stereospecific, removing the pro- $S$ hydrogen from one carbon and the pro- $R$ hydrogen from the other.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1067.jpg?height=218&width=605&top_left_y=1994&top_left_x=603)


Fumarate


Steps 7-8 of FIGURE 29.14: Hydration and Oxidation
The final two steps in the citric acid cycle are the conjugate nucleophilic addition of water to fumarate to yield $(S)$-malate and the oxidation of $(S)$-malate by $\mathrm{NAD}^{+}$to give oxaloacetate. The addition is catalyzed by fumarase and is mechanistically similar to the addition of water to cis-aconitate in step 2 . This reaction occurs through an enolate-ion intermediate, which is protonated on the side opposite the OH , leading to a net anti addition.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1068.jpg?height=351&width=1197&top_left_y=188&top_left_x=464)

The final step is the oxidation of $(S)$-malate by $\mathrm{NAD}^{+}$to give oxaloacetate, a reaction catalyzed by malate dehydrogenase. The citric acid cycle has now returned to its starting point, ready to revolve again. The overall result of the cycle is
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1068.jpg?height=197&width=1532&top_left_y=693&top_left_x=291)


PROBLEM Which of the substances in the citric acid cycle are tricarboxylic acids, thus giving the cycle its 29-10 alternative name?


PROBLEM Write mechanisms for step 2 of the citric acid cycle, the dehydration of citrate and the addition of
29-11 water to aconitate.
PROBLEM Is the pro- $R$ or pro- $S$ hydrogen removed from citrate during the dehydration in step 2 of the citric 29-12 acid cycle? Does the elimination reaction occur with syn or anti geometry?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1068.jpg?height=253&width=799&top_left_y=1245&top_left_x=408)


FIGURE 29.13 MECHANISM - 29.8 Carbohydrate Biosynthesis: Gluconeogenesis

Glucose is the body's primary fuel when food is plentiful, but in times of fasting or prolonged exercise, glucose stores can become depleted. Most tissues then begin metabolizing fats as their source of acetyl CoA, but the brain is different. The brain relies almost entirely on glucose for fuel and is dependent on receiving a continuous supply in the blood. When the supply of glucose fails, even for a brief time, irreversible damage can occur. Thus, a pathway for synthesizing glucose from simple precursors is crucial.


Higher organisms are not able to synthesize glucose from acetyl CoA but must instead use one of the threecarbon precursors lactate, glycerol, or alanine, all of which are readily converted into pyruvate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1068.jpg?height=229&width=800&top_left_y=1929&top_left_x=489)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1068.jpg?height=329&width=852&top_left_y=2183&top_left_x=780)


Pyruvate then becomes the starting point for gluconeogenesis, the 11-step biosynthetic pathway by which organisms make glucose (FIGURE 29.15). The gluconeogenesis pathway is not the reverse of the glycolysis pathway by which glucose is degraded. As with the catabolic and anabolic pathways for fatty acids (Section 29.3 and Section 29.4), the catabolic and anabolic pathways for carbohydrates differ in some details so that both are energetically favorable.


FIGURE 29.15 MECHANISM -

The gluconeogenesis pathway for the biosynthesis of glucose from pyruvate. Individual steps are explained in the text.


FIGURE 29.15 MECHANISM -


FIGURE 29.15 MECHANISM -

Phosphoenolpyruvate
(3) Conjugate nucleophilic addition of water
to the double bond of phosphoenolpyruvate 3 (
gives 2 -phosphoglycerate $\ldots$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1070.jpg?height=109&width=199&top_left_y=951&top_left_x=1077)


FIGURE 29.15 MECHANISM -

5 Phosphorylation of the carboxyl group by reaction with ATP yields 1,3-bisphosphoglycerate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1070.jpg?height=142&width=156&top_left_y=1542&top_left_x=1104)


FIGURE 29.15 MECHANISM -

Step 1 of FIGURE 29.15: Carboxylation
Gluconeogenesis begins with the carboxylation of pyruvate to yield oxaloacetate. The reaction is catalyzed by pyruvate carboxylase and requires ATP, bicarbonate ion, and the coenzyme biotin, which acts as a carrier to transport $\mathrm{CO}_{2}$ to the enzyme active site. The mechanism is analogous to that of step 3 in fatty-acid biosynthesis (FIGURE 29.6), in which acetyl CoA is carboxylated to yield malonyl CoA.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1072.jpg?height=703&width=1423&top_left_y=188&top_left_x=351)


FIGURE 29.15 MECHANISM -

Step 2 of FIGURE 29.15: Decarboxylation and Phosphorylation
Decarboxylation of oxaloacetate, a $\beta$-keto acid, occurs by the typical retro-aldol mechanism like that in step 3 in the citric acid cycle (FIGURE 29.14), and phosphorylation of the resultant pyruvate enolate ion by GTP occurs concurrently to give phosphoenolpyruvate. This reaction is catalyzed by phosphoenolpyruvate carboxykinase.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1072.jpg?height=513&width=1261&top_left_y=1104&top_left_x=432)


FIGURE 29.15 MECHANISM -

Steps 3-4 of FIGURE 29.15: Hydration and Isomerization
Conjugate nucleophilic addition of water to the double bond of phosphoenolpyruvate gives 2-phosphoglycerate by a process similar to that of step 7 in the citric acid cycle. Phosphorylation of C3 and dephosphorylation of C2 then yields 3-phosphoglycerate. Mechanistically, these steps are the reverse of steps 9 and 8 in glycolysis (FIGURE 29.8), which have equilibrium constants near 1 so that substantial amounts of reactant and product are both present.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1072.jpg?height=280&width=1517&top_left_y=1909&top_left_x=304)

Steps 5-7 of FIGURE 29.15: Phosphorylation, Reduction, and Tautomerization
Reaction of 3-phosphoglycerate with ATP generates the corresponding acyl phosphate, 1,3-bisphosphoglycerate, which binds to the glyceraldehyde 3-phosphate dehydrogenase by a thioester bond to a cysteine residue. Reduction of the thioester by $\mathrm{NADH} / \mathrm{H}^{+}$yields the corresponding aldehyde, and keto-enol tautomerization of the aldehyde gives dihydroxyacetone phosphate. All three steps comprise a mechanistic reversal of the corresponding steps 7,6 , and 5 of glycolysis and have equilibrium constants near 1.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1073.jpg?height=530&width=1435&top_left_y=174&top_left_x=345)


FIGURE 29.15 MECHANISM -

Step 8 of FIGURE 29.16: Aldol Reaction
Dihydroxyacetone phosphate and glyceraldehyde 3-phosphate, the two 3-carbon units produced in step 7, join by an aldol reaction to give fructose 1,6-bisphosphate, the reverse of step 4 in glycolysis (FIGURE 29.11). As in glycolysis, the reaction is catalyzed in plants and animals by a class I aldolase and takes place on an iminium ion formed by reaction of dihydroxyacetone phosphate with a side-chain lysine $-\mathrm{NH}_{2}$ group on the enzyme. Loss of a proton from the neighboring carbon then generates an enamine, an aldol-like reaction ensues, and the product is hydrolyzed.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1073.jpg?height=451&width=1714&top_left_y=1038&top_left_x=238)


FIGURE 29.15 MECHANISM -

Steps 9-10 of FIGURE 29.16: Hydrolysis and Isomerization
Hydrolysis of the phosphate group at C1 of fructose 1,6-bisphosphate gives fructose 6-phosphate. Although the result of the reaction is the exact opposite of step 3 in glycolysis, the mechanism is not. In glycolysis, phosphorylation is accomplished by reaction of fructose with ATP, with formation of ADP as by-product. The reverse of that process, however-the reaction of fructose 1,6-bisphosphate with ADP to give fructose 6-phosphate and ATP-is energetically unfavorable because ATP is too high in energy. Thus, an alternative pathway is used in which the C1 phosphate group is removed by a direct hydrolysis reaction, catalyzed by fructose 1,6-bisphosphatase.


FIGURE 29.15 MECHANISM -

Following hydrolysis, keto-enol tautomerization of the carbonyl group from C 2 to C 1 gives glucose 6-phosphate. The isomerization is the reverse of step 2 in glycolysis.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1073.jpg?height=329&width=1473&top_left_y=2020&top_left_x=326)


FIGURE 29.15 MECHANISM -

Step 11 of FIGURE 29.16: Hydrolysis
The final step in gluconeogenesis is the conversion of glucose 6-phosphate to glucose by a second phosphatasecatalyzed hydrolysis reaction. As just discussed for the hydrolysis of fructose 1,6-bisphosphate in step 9, and for the same energetic reasons, the mechanism of the glucose 6-phosphate hydrolysis is not the exact opposite
of the corresponding step 1 in glycolysis.
Interestingly, however, the mechanisms of the two phosphate hydrolysis reactions in steps 9 and 11 are not the same. In step 9, water is the nucleophile, but in the glucose 6-phosphate reaction of step 11, a histidine residue on the enzyme attacks phosphorus, giving a phosphoryl enzyme intermediate that subsequently reacts with water.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1074.jpg?height=554&width=1395&top_left_y=460&top_left_x=365)


FIGURE 29.15 MECHANISM -

The overall result of gluconeogenesis is summarized by the following equation:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1074.jpg?height=261&width=1337&top_left_y=1078&top_left_x=391)


FIGURE 29.15 MECHANISM -

PROBLEM Write a mechanism for step 6 of gluconeogenesis, the reduction of 3-phosphoglyceryl phosphate 29-13 with $\mathrm{NADH} / \mathrm{H}^{+}$to yield glyceraldehyde 3-phosphate.


FIGURE 29.15 MECHANISM - 29.9 Catabolism of Proteins: Deamination

The catabolism of proteins is much more complex than that of fats and carbohydrates because each of the 20 $\alpha$-amino acids is degraded through its own unique pathway. The general idea, however, is that (1) the $\alpha$ amino group is first removed as ammonia by a deamination process, (2) the ammonia is converted into urea, and (3) the remaining amino acid carbon skeleton (usually an $\alpha$-keto acid) is converted into a compound that enters the citric acid cycle.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1074.jpg?height=475&width=1026&top_left_y=1779&top_left_x=547)


Transamination -

Deamination is usually accomplished by a transamination reaction in which the $-\mathrm{NH}_{2}$ group of the amino acid is exchanged with the keto group of $\alpha$-ketoglutarate, forming a new $\alpha$-keto acid plus glutamate. The overall process occurs in two parts, is catalyzed by aminotransferases, and involves participation of the coenzyme pyridoxal phosphate, abbreviated PLP, a derivative of pyridoxine (vitamin $\mathrm{B}_{6}$ ). The aminotransferases differ in their specificity for amino acids, but the mechanism remains the same.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1075.jpg?height=218&width=1359&top_left_y=189&top_left_x=383)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1075.jpg?height=423&width=706&top_left_y=439&top_left_x=704)


Transamination -

The mechanism of the first part of transamination is shown in FIGURE 29.17. The process begins with reaction between the $\alpha$-amino acid and pyridoxal phosphate, which is covalently bonded to the aminotransferase by an imine linkage between the side-chain $-\mathrm{NH}_{2}$ group of a lysine residue in the enzyme and the PLP aldehyde group. Deprotonation/reprotonation of the PLP-amino acid imine effects tautomerization of the imine $\mathrm{C}=\mathrm{N}$ bond, and hydrolysis of the tautomerized imine gives an $\alpha$-keto acid plus pyridoxamine phosphate (PMP).


Transamination -

FIGURE 29.17 MECHANISM


Transamination -

Mechanism for the enzyme-catalyzed, PLP-dependent transamination of an $\alpha$-amino acid to give an $\boldsymbol{\alpha}$-keto acid. Individual steps are explained in the text.
(1) An amino acid reacts with the enzyme-bound PLP imine by nucleophilic addition of its $-\mathrm{NH}_{2}$ group to the $\mathrm{C}=\mathrm{N}$ bond of the imine, giving a PLP-amino acid imine and releasing the enzyme
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1076.jpg?height=302&width=602&top_left_y=418&top_left_x=1122)

PLP-amino acid imine (Schiff base)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1076.jpg?height=432&width=568&top_left_y=716&top_left_x=1093)
(2) Deprotonation of the acidic $\alpha$ carbon of the amino acid gives an intermediate $\alpha$-keto acid imine . . .
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1076.jpg?height=418&width=532&top_left_y=1146&top_left_x=1119)
(3).. that is reprotonated on the PLP carbon. The net result of this deprotonation/reprotonation sequence is tautomerization of the imine $C=N$ bond.
$\alpha$-Keto acid imine tautomer
(4) Hydrolysis of the $\alpha$-keto acid imine by nucleophilic addition of water to the $\mathrm{C}=\mathrm{N}$ bond gives the transamination products pyridoxamine
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1076.jpg?height=391&width=530&top_left_y=1561&top_left_x=1112) ـ
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1076.jpg?height=316&width=534&top_left_y=1642&top_left_x=1110) phosphate (PMP) and $\alpha$-keto acid.


Transamination -

Pyridoxamine phosphate
(PMP)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1076.jpg?height=391&width=614&top_left_y=1970&top_left_x=1116)


Transamination -

Step 1 of FIGURE 29.17: Transimination
The first step in transamination is transimination-the reaction of the PLP-enzyme imine with an $\alpha$-amino acid
to give a PLP-amino acid imine plus expelled enzyme as the leaving group. The reaction occurs by nucleophilic addition of the amino acid $-\mathrm{NH}_{2}$ group to the $\mathrm{C}=\mathrm{N}$ bond of the PLP imine, much as an amine adds to the $\mathrm{C}=\mathrm{O}$ bond of a ketone or aldehyde in a nucleophilic addition reaction (Section 19.8). The protonated diamine intermediate undergoes a proton transfer and expels the lysine amino group in the enzyme to complete the step.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1077.jpg?height=819&width=1424&top_left_y=436&top_left_x=345)

Steps 2-4 of FIGURE 29.17: Tautomerization and Hydrolysis
Following formation of the PLP-amino acid imine in step 1, a tautomerization of the $\mathrm{C}=\mathrm{N}$ bond occurs in step 2. The basic lysine residue in the enzyme that was expelled as a leaving group during transimination deprotonates the acidic $\alpha$ position of the amino acid, with the protonated pyridine ring of PLP acting as the electron acceptor. Reprotonation occurs on the carbon atom next to the ring, generating a tautomeric product that is the imine of an $\alpha$-keto acid with pyridoxamine phosphate, abbreviated PMP.


Transamination -

Hydrolysis of this PMP- $\alpha$-keto acid imine then completes the first part of the transamination reaction. This is the mechanistic reverse of imine formation and occurs by nucleophilic addition of water to the imine, followed by proton transfer and expulsion of PMP as leaving group.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1078.jpg?height=903&width=1324&top_left_y=180&top_left_x=403)


Regeneration of PLP from PMP -

With PLP plus the $\alpha$-amino acid now converted into PMP plus an $\alpha$-keto acid, PMP must be transformed back into PLP to complete the catalytic cycle. The conversion occurs by another transamination reaction, this one between PMP and an $\alpha$-keto acid, usually $\alpha$-ketoglutarate. The products are PLP plus glutamate, and the mechanism is the exact reverse of that shown in FIGURE 29.17. That is, PMP and $\alpha$-ketoglutarate give an imine; the PMP- $\alpha$-ketoglutarate imine undergoes tautomerization of the $\mathrm{C}=\mathrm{N}$ bond to give a PLP-glutamate imine; and the PLP-glutamate imine reacts with a lysine residue on the enzyme in a transimination process to yield PLP-enzyme imine plus glutamate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1078.jpg?height=377&width=1499&top_left_y=1492&top_left_x=313)


Regeneration of PLP from PMP -

PROBLEM Write all the steps in the transamination reaction of PMP with $\alpha$-ketoglutarate plus a lysine residue
29-14 in the enzyme to give the PLP-enzyme imine plus glutamate.
PROBLEM What $\alpha$-keto acid is formed on transamination of leucine?
29-15
PROBLEM From what amino acid is the following $\alpha$-keto acid derived?
29-16
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1078.jpg?height=280&width=456&top_left_y=2191&top_left_x=425)


Regeneration of PLP from PMP - 29.10 Some Conclusions about Biological Chemistry

As promised in the chapter introduction, the past few sections have been a fast-paced tour of a large number of reactions. Following it all undoubtedly required a lot of work and a lot of page-turning to look at earlier sections.


After examining the various metabolic pathways, perhaps the main conclusion about biological chemistry is the remarkable similarity between the mechanisms of biological reactions and the mechanisms of laboratory reactions. If you were to look at the steps of vitamin $B_{12}$ biosynthesis, you would see the same kinds of reactions we've been seeing throughout the text-nucleophilic substitutions, eliminations, aldol reactions, nucleophilic acyl substitutions, and so forth. There are, of course, some complexities, but the fundamental mechanisms of organic chemistry remain the same, whether in the laboratory with smaller molecules or in organisms with larger molecules.
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Succinyl CoA
$+\quad \longrightarrow$
<img class="imgSvg" id = "m6sn3qc88qam2y45r0m" src="data:image/svg+xml;base64,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Glycine
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1079.jpg?height=649&width=822&top_left_y=697&top_left_x=844)


Vitamin $B_{12}$-cyanocobalamin


So what is there to be learned from studying metabolism? One good answer is given in the following Chemistry Matters, which relates the story of how knowledge of a biosynthetic pathway led to the design of new drugs that have saved millions of lives.


(80) CHEMISTRY MATTERS -


Statin Drugs -

Coronary heart disease-the buildup of cholesterol-containing plaques on the walls of heart arteries-is the leading cause of death for people older than 20 in industrialized countries. It's estimated that up to one-third of women and one-half of men will develop the disease at some point in their lives.


Statin Drugs -

The onset of coronary heart disease is directly correlated with blood cholesterol levels (see the Chapter 27 Chemistry Matters), and the first step in disease prevention is to lower those levels. It turns out that only about $25 \%$ of your blood cholesterol comes from what you eat; the remaining $75 \%$-about 1 gram each day-is biosynthesized in your liver from dietary fats and carbohydrates. Thus, any effective plan for lowering your cholesterol level means limiting the amount that your body makes, which is where a detailed chemical knowledge of cholesterol biosynthesis comes in.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1080.jpg?height=830&width=828&top_left_y=867&top_left_x=643)


Statin Drugs -

FIGURE 29.18 The buildup of cholesterol deposits inside arteries can cause coronary heart disease, a leading cause of death for adults in industrialized nations.


Statin Drugs -

We saw in Section 27.5 and Section 27.7 that all steroids, including cholesterol, are biosynthesized from the triterpenoid lanosterol, which in turn comes from acetyl CoA through isopentenyl diphosphate. If you knew all the mechanisms for all the chemical steps in cholesterol biosynthesis, you might be able to devise a drug that would block one of those steps, thereby short-circuiting the biosynthetic process and controlling the amount of cholesterol produced.


Statin Drugs -

But we do know those mechanisms! Look back at the pathway for the biosynthesis of isopentenyl diphosphate from acetyl CoA, shown in FIGURE 27.8. It turns out that the rate-limiting step in the pathway is the reduction of 3-hydroxy-3-methylglutaryl CoA (abbreviated HMG-CoA) to mevalonate, brought about by the enzyme HMGCoA reductase. If that enzyme could be stopped from functioning, cholesterol biosynthesis would also be stopped.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1081.jpg?height=402&width=1372&top_left_y=189&top_left_x=379)


Statin Drugs -

To find a drug that blocks HMG-CoA reductase, chemists did two simultaneous experiments on a large number of potential drug candidates isolated from soil microbes. In one experiment, the drug candidate and mevalonate were added to liver extract; in the second experiment, only the drug candidate was added without mevalonate. If cholesterol was produced only in the presence of added mevalonate but not in the absence of mevalonate, the drug candidate must have blocked the enzyme for mevalonate synthesis.


Statin Drugs -

The drugs that block HMG-CoA reductase, and thus control cholesterol synthesis in the body, are called statins. In just the 10-year period following their introduction in 1994, the death rate from coronary heart disease decreased by $33 \%$ in the United States.