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MONOSACCHARIDES Monosaccharides are carbohydrates that cannot be hydrolyzed to obtain smaller molecules of carbohydrate. White crystalline solids, very soluble in water, have sweet taste.
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# CarbonsCategory NameRelevant examples 3Triose Glyceraldehyde, Dihydroxyacetone 4TetroseErythrose 5Pentose Ribose, Ribulose, Xylulose 6Hexose Glucose, Galactose, Mannose, Fructose 7HeptoseSedoheptulose 9Nonose Neuraminic acid, also called sialic acid
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Hexoses hexose. Three common sugars share the same molecular formula: C 6 H 12 O 6. Because of their six carbon atoms, each is a hexose. They are: glucose blood sugar glucose, "blood sugar", the immediate source of energy for cellular respiration galactose galactose, a sugar in milk (and yogurt), and fructose, a sugar found in honey.
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D-Glucose (Grape Sugar) Glucose is by far the most common carbohydrate and classified as a monosaccharide, an aldose, a hexose a hexose, and is a reducing sugar. dextrose It is known as dextrose, because it is dextrorotatory dextrorotatory
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For sugars with more than one chiral center, D or L refers to the asymmetric C farthest from the aldehyde or keto group.
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Occurrence Widely distributed in nature Occurs in combination with other sugars forming disaccharides Sucrose Maltose Lactose Commercially obtained from starch
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blood sugar Glucose is also called blood sugar 60-100 mg/dL circulates in the blood at a concentration of 60-100 mg/dL of blood in the fasting condition Normally trace amounts pass out in urine Increased amounts in diabetes mellitus. 74% as sweet as sucrose
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Chemistry pyranose and furanose Glucose can occur both in pyranose and furanose forms Pyranose Pyranose form is more predominant due to stable ring
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D-glucose: the chair conformer Four of the five bulky groups (OH and CH 2 OH on C 2,3,4,5) on the ring are in the more stable equitorial positions!
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D-fructose Fruit sugarLevulose
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Fructose Fructose is classified as a: monosaccharide, the most important ketose sugar, a hexose, and is a reducing sugar. Fructose, along with glucose are the monosaccharides found in disaccharide, sucrose.
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Sweetest of all sugars. 73% as sweet as sucrose Fermented by yeast Pyranose form levorotatory Furanose form dextrorotatory
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Occurrence Occurs in plant kingdom as such OR OR in combination with glucose forming Sucrose Animal tissues also contain it in small amounts
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Hydrolysis of cane sugar and of inulin. Can be changed to glucose in the liver and so used in the body. Main source of energy for the spermatozoa Levorotatorydextrorotatory Levorotatory (in sucrose dextrorotatory) Shows mutarotation
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Mutarotation Unlike the other stereoisomeric forms, α and β anomers spontaneously interconvert in solution. This is called mutarotation.
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Galactose Galactose is classified as a: monosaccharide, aldose an aldose, hexose a hexose, reducing sugar and is a reducing sugar. Dextrorotatory shows mutarotation
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Occurrence Galactose is more commonly found in the disaccharide, lactose or milk sugar. seed coat of legumes It is found in seed coat of legumes. 32% as sweet as sucrose C-4 epimer C-4 epimer of glucose galactolipids Galactose is part of nervous tissues as galactolipids
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D-mannose tuberculoprotein Present in the polysacchride component of tuberculoprotein If ingested, it is absorbed and converted to glucose in the body C-2 epimer C-2 epimer of glucose Ozasone test Cannot be differentiated from glucose by Ozasone test
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Pentoses Occur widely in animal and plant kingdom as component of polysacchride Arabinose and xylose- glycoproteins Ribose - RNA, ATP, GTP, NAD +, Coenzymes Deoxyribose - DNA
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Properties May be aldoses or ketoses phenylhadrazine Form ozasone crystals with phenylhadrazine furfural with acids converted to furfural, are strong reducing sugars Not fermented by yeast
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Deoxy sugars Ribose and its related compound, deoxyribose, are the building blocks of the backbone chains in nucleic acids, better known as DNA and RNA. Ribose is used in RNA and deoxyribose is used in DNA.
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The presence or absence of the -OH group on carbon (#2) is an important distinction between ribose and deoxyribose. Ribose has an alcohol at carbon # 2, while deoxyribose does not have the alcohol group. Deoxyribose give most of sugar reaction but do not form ozasones
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Disaccharides Three common disaccharides: Sucrose — common table sugar = glucose + fructose Lactose — major sugar in milk = glucose + galactose Maltose — product of starch digestion = glucose + glucose
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The resulting linkage between the sugars is called a glycosidic bond. The molecular formula of each of these disaccharides isC 12 H 22 O 11 = 2 C 6 H 12 O 6 − H 2 O
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Sucrose Sucrose is made from glucose and fructose units Sucrose or table sugar Cane, beet sugar, Pineapple Has no free anomeric carbon Is a non-reducing sugar No osazone crystals
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Dextrorotatory on hydrolysis becomes levorotary Invert sugar Invert sugar 30% more sweet than sucrose Honey is rich with invert sugar In sucrase deficiency, malabsorption leads to diarrhea and flatulence
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Maltose Glucose+ Glucose slivary amylase on starch Formed in vivo by action of slivary amylase on starch acidic hydrolysis of starch In vitro formation by acidic hydrolysis of starch. Reducing sugar Has free anomeric carbon forms osazone crystals Shows mutarotation 32% as sweet as sucrose Baby and invalid foods
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Lactose Glucose + Galactose Milk sugar Reducing sugar In lactase deficiency, malabsorption leads to diarrhea and flatulence Certain bacteria can ferment lactose to lactic acid - souring of milk. ( lactobacillus bulgaricus) 16% as sweet as sucrose (least sweet sugar)
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