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Lecture 4 Fatty Acid Oxdn - BergTymoczkoStryer Biochemistry...

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Biochemistry Chapter 12.1: Fatty Acids Chapter 22: Fatty Acid Metabolism Copyright  ©  by W. H. Freeman and Company   Berg • Tymoczko • Stryer
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Fatty Acids: carboxylic acids with long hydrocarbon chains of variable length and degree of unsaturation
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Structure of two fatty acids 16:0 18:1 9 # carbons: # double bonds saturated monounsaturated
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Name derived from hydrocarbon 1 double bond: -en oic acid 2 double bonds: -di enoic acid n: unbranched
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most common * * * essential
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Length affects Tm: Long hydrocarbon chains interact more strongly than short (Tm increases with increasing chain length) Double bonds affect Tm: A cis double bond introduces a bend which interferes with packing of the hydrocarbon chains, lowering Tm Fluidity of fatty acids depends on chain length and degree of unsaturati
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Chain length and degree of unsaturation determine the fluidity of fatty acids, their derivatives, and membranes The melting point of a fatty acid increases with chain length Stearic acid 18:0 melting point: 69.6 o C Palmitic acid 16:0 melting point: 62.5 Myristic acid 14:0 melting point: 53.9 Melting point decreases with number of double bonds (same chain length) Stearic acid 18:0 melting point: 69.6 o C Oleic acid 18:1 melting point: 13.4 o C Linoleic 18:2 melting point: -5 Lipids with lower melting points (short, unsaturated) are more fluid at body temperature and contribute to the fluidity of cellular membranes
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most naturally occurring fatty acids contain cis double bonds N Engl J Med (2006) 354: 1601-13 Estimate: eliminating industrial produced trans fat would avert 72,000 to 228,000 (6-20%) coronary heart disease events per year
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Four major physiological roles of fatty acids: 1)fuel molecules 2) Building blocks of phospholipids and glycolipids: amphipathic molecules that comprise biological membranes 3) Signals to membrane localize proteins 4) Hormones and second messengers (signaling molecules): steroid hormones- long-range intercellular messengers prostaglandins- short range inter- and intracellular messengers diacylglycerols- intracellular second messengers
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Advantages of Fat over Carbohydrate for Energy Storage 70 kg person (155 lb) 24 lb triacylglycerol = 100,000 kcal Protein = 24,000 kcal Glycogen = 600 kcal
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