Chemistry of nutrients Course 2 Energy Vladimíra Kvasnicová

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1 Chemistry of nutrients Course 2 Energy - 39 Vladimíra Kvasnicová

2 Energy in a diet SACCHARIDES / LIPIDS / PROTEINS 60 : 30 : kj/g 37 kj/g 17 kj/g 4 kcal/g 9 kcal/g 4 kcal/g -CH(OH)- -CH 2 - -CH(NH 2 )- CO 2, H 2 O CO 2, H 2 O CO 2, H 2 O, NH 3

3 17 kj/g monosaccharides oligosaccharides polysaccharides

4 MONOSACCHARIDES

5 Monosaccharides Glucose Galactose Fructose Glucuronic acid Ribose

6 DISACCHARIDES SALAME SAcharose (= sucrose) LActose MaltosE saccharose has not reducing properties

7 free anomeric (= hemiacetal) hydroxyl reducing properties α-glc(1 4)Glc β-gal(1 4)Glc α-glc(1 2)β- Fru The figure has been adopted from J.Koolman, K.H.Röhm / Color Atlas of Biochemistry, 2nd edition, Thieme 2005

8 POLYSACCHARIDES homopolysaccharides starch, glycogen, cellulose, inuline heteropolysaccharides glycoproteins, proteoglycans storage starch, glycogen, inuline structural cellulose, proteoglycans branched unbranched

9 STARCH (Glc) n amylose (maltose) n α(1 4) glycosidic bonds amylopectine α(1 4) glycosidic bonds α(1 6) glycosidic bonds The figures have been adopted from Harper s Biochemistry

10 GLYCOGEN (Glc) n OH nonreducing end reducing end The figure is found at (October 2007)

11 CELLULOSE β-glc(1 4)Glc The figures are found at (October 2007)

12 Monosaccharides form phosphoric acid esters ( phosphates ) in cells their carbon skeleton is partially oxidized : -CH(OH)- (less energy produced when it is oxidized in metabolism) energy source Glc, Fru, Gal / energy storage - glycogen conversion to other saccharides (components of nucleotides, glycoproteins) or saccharide derivatives (aminosugars, uronic acids in proteoglycans) conversion to fat (energy storage) important intermediates of their metabolism: glyceraldehyde-3-phosphate dihydroxyacetone phosphate (DHAP) 1,3-bisphosphoglycerate anhydride bond

13 glucose Monosaccharides energy production (glycolysis) energy storage (glycogen or conversion to fat) conversion to other saccharides, e.g. ribose (pentose phosphate cycle) conversion to glucuronic acid (oxidation of glucose) fructose conversion to glucose energy production (glycolysis) energy storage (conversion to fat) galactose conversion to glucose and lactose ribose synthesis of glycoproteins and proteoglycans nucleotide synthesis

14 lipids 37 kj/g

15 Free fatty acids (FFA) Esterified fatty acids ω-9 = triacylglycerol (TAG) or triglyceride ω-6 ω-3

16 The figure is found at 2/ch11_cholesterol.jpg (Jan 2007)

17 Fatty acids (FA) saturated fat contains saturated FA (more energy: -CH 2 -CH 2 -) monounsaturated fat / polyunsaturated fat (less energy partially oxidized: -CH=CH-) even number of carbons (synthesized from C-2 precursor) separated cis double bonds: -CH=CH-CH 2 -CH=CH- short chain fatty acids (SCFA): less than 6 carbons medium chain fatty acids (MCFA): 6 12 carbons long chain fatty acids (LCFA): more than 12 carbons very long chain fatty acids (VLCFA): more than 22 carbons

18 The figure was adopted from: J.Koolman, K.H.Röhm / Color Atlas of Biochemistry, 2 nd edition, Thieme 2005

19 Fatty acids (FA) in cells they are bound to Coenzyme A acyl-coa binding place more reduced carbon skeleton than saccharides: -CH 2 - FA are components of triacylglycerols, phospholipids, cholesterol esters (= hydrolyzable lipids) FA are used for energy production (β-oxidation) or energy storage in a form of triacylglycerols = neutral fat FA can be converted to ketone bodies, eicosanoids

20 blood lipids The figure was accepted from the book: Grundy, S.M.: Atlas of lipid disorders, unit 1. Gower Medical Publishing, New York, 1990.

21 proteins 17 kj/g N NH 3 urea, S H 2 SO 4 sulfates

22 Amino acids (AA) contain other elements: nitrogen (all AA), sulfur (Cys, Met) when AA are degraded ammonia NH 3 (and H 2 SO 4 ) are produced NH 3 is toxic it must be converted to urea excreted with urine AA are primarily used for proteosynthesis other use: synthesis of N-containing compounds (heme, nucleotides, signal molecules hormones, neurotransmitters) direct energy production (Krebs cycle) or indirec energy production during fasting: after conversion to glucose (gluconeogenesis) energy storage after conversion to fat the use of AA as energy substrates consumes energy because ammonia must be detoxified!

23 Amino acids

24

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