The biosynthesis of cholesterol as outlined in Figure 26.10 is admittedly quite complicated. It will aid your
Question:
(a) Which two hydrogen atoms of squalene 2,3-epoxide are the ones that migrate in step 3?
(b) Which methyl group of squalene 2,3-epoxide becomes the methyl group at the C, D ring junction of cholesterol?
(c) What three methyl groups of squalene 2,3-epoxide are lost during the conversion of lanosterol to cholesterol?
FIGURE 26.10
The biosynthetic conversion of squalene to cholesterol proceeds through lanosterol. Lanosterol is formed by a cyclization reaction of squalene-2,3-epoxide.
Question continue over next page
Step i : Squalene undergoes enzymic oxidation to the 2.3-epoxide. This reaction has been described earlier. in Section 16.14. Squalene O, NADEL enzyme Squalene 2.3-epoxide Step 2: Cyclization of squalene 2,3-epoxide, shown in its coiled form, is triggered by ring opening of the epoxide. Cleavage of the carbon-oxygen bond is assisted by protonation of oxygen and by nucleophilic participation of the r electrons of the neighboring double bond. A series of ring closures leads to the tetracyclic carbocation shown. Squalene 2.3-epoxide Tetracyclic carbocation Step 3: Rearrangement of the tertiary carbocation formed by cyclization produces lanosterol. Two hydride shifts, from C-17 to C-20 and from C-13 to C-17, are accompanied by methyl shifts from C-14 to C-13 and from C-8 to C-14. A double bond is formed at C-8 by loss of the proton at C-9 HO Tetracyclic carbocation formed in step 2 Lanoster -Cont Step 4: A series of enzyme-catalyzed reactions converts lanosterol to cholesterol. The three highlighted methyl groups in the structural formula of lanosterol are lost via separate multistep operations, the C-8 and C-24 double bonds are reduced, and a new double bond is introduced at C-5. НС many ste но 24 Lanosterol Cholesterol
Step by Step Answer:
a The hydrogens that migrate in step 3 are those at C13 ...View the full answer
Related Video
Lemon juice preserves apples by slowing down the oxidation process. Oxidation is a chemical reaction that occurs when oxygen reacts with certain substances, such as apples. When an apple is cut or bitten, oxygen is exposed to the inside of the apple and causes enzymes in the apple to turn brown, which is an indication of oxidation. The browning process is caused by the production of polyphenol oxidase (PPO) enzymes that convert phenolic compounds into quinones, which then polymerize to form the brown pigments. One of the compounds present in lemon juice is ascorbic acid (vitamin C), which is a natural antioxidant. Antioxidants work by neutralizing the free radicals that cause oxidation. When lemon juice is applied to apples, the ascorbic acid in the lemon juice reacts with the PPO enzymes and slows down the browning process. You can do an experiment by cutting apples into small pieces, leaving one apple piece in contact with air and the others covered with lemon juice and compare the browning process. This will help to understand the antioxidation process in fruits.
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