ANSC 689 PHYSIOLOGICAL CHEMISTRY OF LIVESTOCK SPECIES Carbohydrate Chemistry
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1 I. General structures A. D-Aldoses ANSC 689 PHYSIOLOGICAL CHEMISTRY OF LIVESTOCK SPECIES 1. All monosaccharides are aldehydes or ketones with multiple hydroxyl groups (i.e., alcohol groups). 2. Smallest is D-glyceraldehyde (as in glyceraldehyde-3-phosphate in glycolysis). 3. Nutritionally most important is D- glucose. 4. L-forms are mirror images. B. D-Ketoses 1. Smallest is D-dihydroxyacetone (as in dihydroxyacetone-phosphate). 2. Nutritionally most important is D- fructose. 3. Free aldehydes are ketones are reducing sugars. In the presence of heat and OH - they reduce cations. 1
2 C. Formation of ring structures 1. Six-sided pyranoses form when the free aldehyde end of a hexose reacts with one of the C-5 alcohol group to form a hemiacetal. 2. Five-sided furanoses form when the C-2 keto group of a hexose reacts with one of the C-5 alcohol group to form another hemiacetal. D. Monosaccharides and dissacharides 1. Monosaccharides have free reducing ends. 2. Dissacharides can have free reducing ends, and are linked by α-1,4, α-1,2 or ß-1,4-Oglycosidic bonds. E. Nonstructural polysaccharides 1. Amylose the linear subunit of starch and glycogen. Has only α- 1,4 linkages. Soluble. 2
3 2. Amylopectin the branched subunit of some starches and glycogen. Contains both α-1,4 and α-1,6 linkages. Soluble. 3. Starch linear and branched 4. Glycogen only branched F. Structural polysaccharides 1. Cellulose Linear polymers of glucose in ß-1,4 linkage. Insoluble. 2. Hemicellulose (xylans) linear/branched polymers of xylose in ß-1-4 linkages. Insoluble. 3. Pectins linear polymers of galacturonic acid in 1-4 linkages that are neither α or ß. Soluble. 3
4 4. Lignin highly branched polymer of substituted phenylpropranes. Insoluble. G. Structures to memorize: Glucose (open structure and ring structure), indicated above Lactate (end product of glycolysis) Pyruvate (= lactate 2H) Oxaloacetate (= pyruvate + CO 2 ) α-ketoglutarate (= oxaloacetate + CH 2 ) 4
5 II. Dietary sources of carbohydrates Carbohydrate Sources Structure and properties D-Glucose (dextrose) Fruit; traces in most plant foods; honey; maple sugar Water-soluble monosaccharide D-Fructose Fruit; traces in most plant foods; honey; maple sugar Water-soluble monosaccharide D-Galactose Sucrose Component of lactose Cane sugar; beet sugar; fruits; maple sugar Lactose Milk; dairy products Maltose Raffinose Stachynose Amylose Amylopectin (starch) Glycogen (animal starch) Invert sugar Corn syrup Pectins Lignin Cellulose Hemicellulose Sprouted grain; produced during digestion of starches Soybean and cottonseed meals; sugar beets Soybeans Starchy plants; grains Starchy plants; grains; thickener in processed foods Liver; muscle Processed foods Processed foods Fruits Plant cell walls Plant cell walls; wheat bran All land plants 5 Water-soluble monosaccharide Water-soluble disaccharide; α-1,2-linked glu-fru Water-soluble disaccharide; (ß- 1,4-linked gal-glu Water-soluble disaccharide; α-1,4-linked glu-glu Water-soluble trisaccharide; α- 1,6, α-1,2-linked gal-glu-fru Water-soluble tetrasaccharide; α-1,6, a-1,6, α-1,2-linked gal-gal-glu-fru Water-soluble linear polymer of glucose; α-1,4-linked Water-soluble branched polymer of glucose; α-1,4- and a-1,6-linked Water-soluble branched polymer of glucose; α-1,4- and α-1,6-linked Hydrolyzed sugar (much sweeter than sugar) Hydrolyzed starch (i.e., glucose) Water-soluble linear polymers of galacturonic acids and/or modified galacturonic acid; ß-1,4-linked Insoluble highly branched polymer of substituted phenylpropranes; not a carbohydrate Insoluble linear polymer of glucose; ß-1,4-linked Insoluble linear/branched polymer of xylose; ß-1,4-linked;
6 1. Xylan (cellulosan) may contain glucuronic acid. 2. Amorphous encrusting All land plants Insoluble ester linkage of xylose to lignin 6
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