26.1 Acetyl Coenzyme A
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1 Chapter 26 Lipids
2 Lipids Lipids are naturally occurring substances grouped together on the basis of a common property they they are more soluble in nonpolar solvents than in water. Some of the most important of them the ones in this chapter are are related in that they have acetic acid (acetate) as their biosynthetic origin. In many biosynthetic pathways a substance called acetyl coenzyme A serves as the source of acetate.
3 26.1 Acetyl Coenzyme A
4 Structure of Coenzyme A P P P N N 3 C C 3 N N N 2 SR N N R = ; Coenzyme A R = CC 3 ; Acetyl coenzyme A
5 Reactivity of Coenzyme A Nucleophilic acyl substitution C 3 CSCoA Y C 3 C Y + SCoA Acetyl coenzyme A is a source of an acetyl group toward biological nucleophiles; ; it is an acetyl transfer agent.
6 Reactivity of Coenzyme A can react via enol C 3 CSCoA 2 C CSCoA Acetyl coenzyme A reacts with biological electrophiles at its α carbon atom. E E + C 2 CSCoA
7 26.2 Fats, ils, and Fatty Acids
8 Fats and ils C 2 CR' RCC C 2 CR" Fats and oils are naturally occurring mixture of triacylglycerols (also called triglycerides). Fats are solids; oils are liquids.
9 Fats and ils C 2 C(C 2 ) 16 C 3 C 3 (C 2 ) 16 CC C 2 C(C 2 ) 16 C 3 Tristearin; mp 72 C
10 Fats and ils C 2 C(C 2 ) 16 C 3 C 3 (C 2 ) 6 C 2 C 2 (C 2 ) 6 CC C C C 2 C(C 2 ) 16 C 3 2-leyl-1,3-distearylglycerol; mp 43 C
11 Fats and ils 2-leyl-1,3-distearylglycerol mp 43 C 2, Pt Tristearin mp 72 C
12 Fatty Acids R'CC C 2 CR 2 R'C C 2 C CR C 2 CR" C 2 CR" Acids obtained by the hydrolysis of fats and oils are called fatty acids. Fatty acids usually have an unbranched chain with an even number of carbon atoms. If double bonds are present, they are almost always cis.
13 Table 26.1 (p 1018) Systematic name Common name C 3 (C 2 ) 10 C C 3 (C 2 ) 12 C C 3 (C 2 ) 14 C Dodecanoic acid Tetradecanoic acid exadecanoic acid Lauric acid Myristic acid Palmitic acid
14 Table 26.1 (p 1018) Systematic name Common name C 3 (C 2 ) 16 C C 3 (C 2 ) 18 C ctadecanoic acid Icosanoic acid Stearic acid Arachidic acid
15 Table 26.1 (p 1018) C 3 (C 2 ) 7 (C 2 ) 7 C C C Systematic name: (Z)-9-ctadecenoic( acid Common name: leic acid
16 Table 26.1 (p 1018) C 3 (C 2 ) 4 C 2 (C 2 ) 7 C C C C C Systematic name: (9Z,, 12Z)-9,12 9,12-ctadecadienoic acid Common name: Linoleic acid
17 Table 26.1 (p 1018) C 3 C 2 C 2 C 2 (C 2 ) 7 C C C C C C C Systematic name: (9Z,, 12Z,, 15Z)-9,12,15 9,12,15- ctadecatrienoic acid Common name: Linolenic acid
18 Table 26.1 (p 1018) Systematic name: (5Z, 8Z, 11Z,, 14Z)-5,8,11,14 5,8,11,14- Icosatetraenoic acid Common name: Arachidonic acid
19 26.3 Fatty Acid Biosynthesis
20 Fatty Acid Biosynthesis Fatty acids are biosynthesized via acetyl coenzyme A. The group of enzymes involved in the overall process is called fatty acid synthetase. ne of the key components of fatty acid synthetase is acyl carrier protein (ACP S).
21 Fatty Acid Biosynthesis An early step in fatty acid biosynthesis is the reaction of acyl carrier protein with acetyl coenzyme A. C 3 CSCoA + S ACP C 3 CS ACP + SCoA
22 Fatty Acid Biosynthesis A second molecule of acetyl coenzyme A reacts at its α carbon atom with carbon dioxide (as C 3 ) to give malonyl coenzyme A. C 3 CSCoA Acetyl coenzyme A + C 3 CC C 2 CSCoA Malonyl coenzyme A
23 Fatty Acid Biosynthesis Malonyl coenzyme A then reacts with acyl carrier protein. CC C 2 CS ACP ACP S CC C 2 CSCoA Malonyl coenzyme A
24 Fatty Acid Biosynthesis Malonyl ACP and acetyl ACP react by carbon-carbon bond formation, accompanied by decarboxylation. C C 3 C S ACP C 2 CS ACP C 3 C C 2 CS ACP S-Acetoacetyl ACPACP
25 Fatty Acid Biosynthesis In the next step, the ketone carbonyl is reduced to a secondary alcohol. C 3 C C 2 CS ACP NADP C 3 C C 2 CS ACP S-Acetoacetyl ACPACP
26 Fatty Acid Biosynthesis The alcohol then dehydrates. C 3 C C 2 CS ACP C 3 C CCS ACP
27 Fatty Acid Biosynthesis Reduction of the double bond yields ACP bearing an attached butanoyl group. Repeating the process gives a 6-carbon 6 acyl group, then an 8-carbon 8 one, then 10, etc. C 3 C 2 C 2 CS ACP C 3 C CCS ACP
28 26.4 Phospholipids
29 Phospholipids Phospholipids are intermediates in the biosynthesis of triacylglycerols. The starting materials are L-glycerol 3-3 phosphate and the appropriate acyl coenzyme A molecules.
30 C 2 + RCSCoA + R'CSCoA C 2 P 3 2 The diacylated species formed in this step is called a phosphatidic acid. R'C C 2 CR C 2 P 3 2
31 The phosphatidic acid then undergoes hydrolysis of its phosphate ester function. R'C C 2 CR C 2 P 3 2
32 R'C 2 R'C C 2 CR C 2 C 2 CR Reaction with a third acyl coenzyme A molecule yields the triacylglycerol. C 2 P 3 2
33 R'C R"CSCoA R'C C 2 CR C 2 C 2 CR C 2 CR" Reaction with a third acyl coenzyme A molecule yields the triacylglycerol.
34 Phosphatidylcholine Phosphatidic acids are intermediates in the formation of phosphatidylcholine. C 2 CR C 2 CR R'C R'C C 2 P 3 2 C 2 P 2 + (C 3 ) 3 NC 2 C 2
35 Phosphatidylcholine C 2 CR hydrophobic "tail" R'C hydrophobic "tail" C 2 P 2 + (C 3 ) 3 NC 2 C 2 polar "head group"
36 Phosphatidylcholine hydrophobic (lipophilic) "tails" hydrophilic "head group"
37 Cell Membranes water Cell membranes are "lipid bilayers." Each layer has an assembly of phosphatidyl choline molecules as its main structural component. water
38 Cell Membranes water The interior of the cell membrane is hydrocarbon-like. Polar materials cannot pass from one side to the other of the membrane. water
39 26.5 Waxes
40 Waxes Waxes are water-repelling repelling solids that coat the leaves of plants, etc. Structurally, waxes are mixtures of esters. The esters are derived from fatty acids and long- chain alcohols.
41 Waxes Waxes are water-repelling repelling solids that coat the leaves of plants, etc. Structurally, waxes are mixtures of esters. The esters are derived from fatty acids and long- chain alcohols. C 3 (C 2 ) 14 CC 2 (C 2 ) 28 C 3 Triacontyl hexadecanoate: occurs in beeswax
42 26.6 Prostaglandins
43 Prostaglandins Prostaglandins are involved in many biological processes. Are biosynthesized from linoleic acid (C 18 ) via arachidonic acid (C 20 ). (See Table 26.1)
44 Examples: PGE 1 and PGF 1α PGE 1 PGF 1α
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