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| Functional and Structural |
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| Asst. prof. Amira Abdel Hamid Kamel |
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| Medical Biochemistry Department |
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| @ Identify different classes of carbohydrates |
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| ® Define chemistry and functions of monosaccharides |
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| oligosaccharides and their derivatives |
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| @ Define and classify polysaccharides. |
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| @ Discuss structure and function medically important homo |
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| and hetero-polysaccharides. |
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| Definition of carbohydrates: Rat RSP |
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| Carbohydrates are aldehyde (CHO) or ketone (C=O) derivatives of |
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| polyhydric alcohols (have more than one OH group) or compounds |
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| which yield these derivatives on hydrolysis. |
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| Importance of carbohydrates: |
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| The chief source of energy and form 60% of human diet. |
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| Important structural components in human cells |
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| Synthesis of antigens e.g. blood group substance. |
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| their receptors & immunoglobulins. |
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| . Hyalouronic acid (polysaccharide) is important for joint |
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| Classification of carbohydrates |
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| According to the number of sugar units in the molecule there are |
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| 1.Monosaccharides (simple sugars): They contain one |
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| i.e., and the simplest form of sugars. |
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| 2.Oligosaccharides: They contain 2 —10 monosaccharide |
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| 3. Polysaccharides: They contain more than 10 |
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| monosaccharide units per molecule. |
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| They are classified according to the number of carbon atoms into: |
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| Trioses: with three carbons |
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| Tetroses: with four carbons |
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| Pentoses: with five carbons |
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| Hexoses: with six carbons |
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| Each of these groups is subdivided according to the type of |
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| functional chemical group into: |
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| Aldoses (sugars containing aldehyde group) |
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| Ketoses (sugars containing ketone group). |
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| Medical significance of some Monosaccharides |
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| ® Ribose: is structural component in nucleic acids & free nucleotides. |
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| blood sugar or dextrose). Other hexoses |
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| have to be converted into glucose to be utilized in the body. It |
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| appears in urine in diabetes mellitus. |
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| @ Mannose: is a subunit in glycoproteins and sialic acid that enters in |
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| the structure of gangliosides. |
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| ® Galactose: is the subunit of the milk sugar lactose. It enters in |
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| structure of glycolipids and glycoproteins. |
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| fruit sugar, levulose): It is the sweetest |
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| sugar known. It is the main sugar in bee’s honey. |
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| Sugar derivatives of monosaccharides with |
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| 1.Amino sugars or sugaramines (Replace hydroxyl |
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| group at C2 by an amino group). |
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| 2.Deoxy sugars (Replace hydroxyl group at C2 or C3 or |
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Definition
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| 3. Sugar acids (product of oxidation of sugars). |
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| 4. Sugar alcohols (product of reduction of sugars). |
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| 1. Amino sugars (Sugaramines): |
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| - Replace OH group on C2 by an amino group. |
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| 1. Glucosamine (Chitosamine): It enters in the structure of |
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| some mucopolysaccharides. D |
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| 2. Galactosamine (Chondrosamine): It enters in the structure |
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| of the sulfate-containing mucopolysaccharides. |
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| 3. Mannosamine: lt enters in the structure of antibiotics and |
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| important for their activity e.g. |
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| 4. Sialic acid: It enters in structure of glycolipids and |
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| EEL is an amino sugar AAA) |
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| EE deoxy sugar since it contains two hydrogen AD |
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| @ sugar acid since it contains COOH group |
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| 1. Gluconic acid used as Ca’ gluconate for intravenous |
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| supplementation of calcium. |
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| 2. L-ascorbic acid (vitamin C) is synthesized from glucose in plants |
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| primates and guinea pig. It is an |
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| Glucuronic acid: It is synthesized in the liver and important in. |
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| 1. Glucuronic acid enters in the structure of mucopolysaccharides |
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| Detoxication by conjugation of certain drugs and toxins and |
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| help excretion of bilirubin and steroid hormones. |
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Definition
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| 3. L-iduronic acid is an isomer of D-glucuronic acid and it enters in |
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| structure of mucopolysaccharides e.g. Heparin |
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| 1-Glyceraldehyde reduction gives glycerol that enters in structure of |
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| creams and explosives. ST > 7 |
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| 2- Ribose reduction gives Ribitol that is a part of the structure of |
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Definition
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| 3- Glucose reduction gives sorbitol that enters in medical industries. It |
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| can not diffuse out of cells and its accumulates in cells |
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| damage to cells as in cataracts and neuropathy. |
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| 4- Mannose reduction gives Mamnitol which is injected intravenously |
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| to reduce intracranial hypertension. |
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| It is a sugar alcohol of 6 OH groups |
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| It presents in high concentration in bran and it combines with 6 |
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| molecules of phosphoric acid to give phytic acid. Phytic acid |
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| calcium and magnesium salts (phytate) which |
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| hinder absorption of Ca?* |
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| Mg?’ and iron in the intestine. |
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| It presents in high concentration in heart and muscles tissues |
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Definition
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Definition
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| It is considered a member of vitamin B complex because it is |
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| essential for synthesis of phospholipids |
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Definition
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Definition
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| 1- Reducing Disaccharides: ni CH ES |
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| + It has a free aldehyde group {anomeric carbon) |
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Definition
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Definition
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| 2. Non-reducing Disaccharides: |
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Definition
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| * It has no free aldehyde group (anomeric carbon) |
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Definition
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| 1- Reducing Disaccharides: |
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Definition
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Definition
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| + It consists of 2 a-glucose units linked by a-1 |
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Definition
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| * It is a reducing disaccharide. |
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Definition
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| + It gives osazone called maltosazone (Rosette shaped). |
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| * It is produced during digestion of starch by amylase enzyme. |
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Definition
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| + It is hydrolyzed in human intestine by maltase enzyme. |
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| B) Lactose (milk sugar) : el oy |
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| - It is formed of B-galactose and a-glucose linked by B-1 |
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| - ita reducing disaccharide |
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| forms lactosazone that has > |
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| - Itis digestible by lactase into glucose and galactose. |
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Definition
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| - It is excreted physiologically in urine of pregnant and lactating |
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| females (lactosuria) and must be differentiated from pathological |
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| glucosuria caused by diabetes mellitus by: |
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Definition
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| 3. Specific enzymatic reaction such as glucose oxidase. |
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| It is the most suitable sugar for baby feeding as a sweetener for |
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Definition
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| . It is the least sweet sugar so that the baby can nurse a large amount |
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| of mother’s milk without getting his appetite lost. |
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Definition
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| . It is non-fermentable sugar |
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| so it does not form gases and not cause |
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Definition
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| . It has a laxative effect and prevents constipation. |
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Definition
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| 4. Unabsorbed sugar is used as a food for large intestinal bacteria |
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| that form a number of vitamins that benefits the baby. |
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| . It is easily digested and helps absorption of the minerals of milk. |
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| 2. Non-reducing Disaccharides: |
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| Sucrose (Cane or Table sugar): |
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| It is table sugar and sugar of cane and molasses. |
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| It is formed of a-glucose linked to B-fructose by a-B-1 |
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Definition
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| The 2 anomeric carbons (C1 of glucose and C2 of fructose) are |
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| It is hydrolyzed by sucrase enzyme into equal amounts of glucose |
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Definition
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Definition
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| Definition: They contain more than 10 monosaccharide units per |
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Definition
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Definition
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Definition
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| - They are classified into: |
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Definition
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| They produce only one type of monosaccharides on hydrolysis |
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Definition
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Definition
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| They produce several types of sugars on hydrolysis. |
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Definition
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Definition
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| -They are named according to the type of that |
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Definition
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Definition
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| 3. Galactosans: Agar-Agar |
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Definition
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| 4. N-acetyl-glucosans: Chitin |
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Definition
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| Comparison between Starch |
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Definition
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| Starch Glycogen Cellulose |
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Definition
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Definition
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| Stored form of carbohydrate in[Stored form of] Structural form of] |
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Definition
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| plants. The core is amylose carbohydrates in animals. |carbohydrate in plant cells. |
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Definition
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| (20%) and the shell is amylopectin |
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Definition
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| and tubers, ¢.g., potatoes. _|Muscles and liver Linen and cotton |
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| [Amylose is water soluble |
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Definition
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| amylopectin is insoluble. |
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Definition
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| ‘Amylose is helical straight chain (o-| |
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Definition
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| glucose units linked by «-I |
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Definition
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Definition
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| JAmylopectin is branched chain (o-| |
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Definition
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| glucose units linked by a-1 |
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Definition
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Definition
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Definition
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Definition
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| trees are shorter and have} |
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Definition
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Definition
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| Straight chain (large number] |
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Definition
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| of B-glucose units linked by |
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Definition
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Definition
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Definition
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| Is hydrolyzed by HCI or amylase into| |
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Definition
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Definition
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Definition
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Definition
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| hydrolysis gives cellobiose. |
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Definition
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Definition
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Definition
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| @ It is indigestible in humans because of lack of enyzmes that |
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| hydrolyze B- glycosidic linkage |
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Definition
| but it is very essential in human |
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Definition
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| 1. Prevention of constipation by increasing the bulk of stools. |
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Definition
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| 2. Its fermentation by intestinal bacteria give some water soluble |
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Definition
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| vitamins and volatile fatty acids that is anticancer for colon cells. |
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Definition
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| 3. It adsorbs toxins present in foods and prevents its absorption. |
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Definition
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Definition
| It adsorbs cholesterol present in foods and decrease its |
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Definition
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Definition
| It increases gastric emptying time, and so prevents rapid rise of |
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| blood glucose level (This is beneficial for dieters and diabetics). |
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Definition
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| 6. It prevents cancer colon (volatile fatty acids produced from its |
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Definition
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Term
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Definition
| decrease contact time by stimulating prestalsis and |
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| by adsorbing carcinogens on its surface). |
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Definition
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Definition
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| @ It is synthesized by certain bacteria. |
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Definition
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| 4 It has a great biochemical importance. |
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Definition
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| 1. It is used as plasma substitute to restore blood pressure in |
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Definition
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Definition
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| 2. Combination of dextran with iron used for treatment of iron |
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Definition
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| deficiency anemia by injection. |
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Definition
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| 3. Sodium dextran sulfate is an anticoagulant. |
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Definition
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Definition
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Definition
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Definition
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Definition
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|
Definition
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| They are polysaccharides that on hydrolysis produce several types of sugars. |
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Definition
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Term
| I. Non-nitrogenous heteropolysaccharides: |
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Definition
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Term
| IL. Nitrogenous heteropolysaccharides: Contain sugar amines |
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Definition
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Term
| A) Neutral nitrogenous (Glycoproteins): Does not contain |
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Definition
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Term
|
Definition
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Term
| B) Acidic nitrogenous (Mucopolysaccharides |
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Definition
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| & Proteoglycans) Contain uronic acids |
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Definition
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| > Sulfur-free: Hyaluronic acid |
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Definition
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| > Sulfur-containing: Chondroitin sulfate |
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Definition
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Term
| A- Neutral Nitrogenous Heteropolysaccharides: |
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Definition
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Term
|
Definition
|
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Term
| - They do not contain uronic acids or sulfate groups. |
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Definition
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| - They are formed of a large protein core and smaller branched |
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Definition
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Term
|
Definition
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Term
| B- Acidic Nitrogenous Heteropolysaccharides: |
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Definition
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|
Definition
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|
Definition
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|
Definition
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|
Definition
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|
Definition
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| * Proteoglycans: (mucopolysaccharides + proteins). |
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Definition
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| * They consist of very small core protein molecule and a huge |
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Definition
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Term
| carbohydrate tree that is highly complex in the form of repeating |
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Definition
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|
Definition
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Term
|
Definition
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Term
|
Definition
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| Acidic Nitrogenous Heteropolysaccharides: |
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Definition
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Term
| Sulfur free Mucopolysaccharides |
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Definition
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Term
|
Definition
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Term
| It is formed of N-acetyl glucosamine linked to glucuronic acid. It is formed |
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Definition
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Term
| of 400 - 4000 repeating disaccharide units. |
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Definition
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Term
| Hyaluronic acid is unique among the GAGs in that: |
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Definition
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Term
|
Definition
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Term
| 2- It is not found covalently attached to proteins as a proteoglycan |
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Definition
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| 3- Only GAG present both in animals and bacteria |
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Definition
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Term
|
Definition
|
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Term
|
Definition
|
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| . The molecule is coiled and entwined making a very firm gel which |
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Definition
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| prevents bacterial invasion of the skin. |
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Definition
|
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Term
| . It is present in connective tissue matrix |
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Definition
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Term
|
Definition
| in the skin, synovial fluid, around the ovum, and in the |
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| umbilical cord to preserve the full-form of these structures. |
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Definition
|
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Term
| . Hyaluronic acid imbibes water and forms a incompressible |
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Definition
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Term
| substance due to the presence of several OH groups causing |
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Definition
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Term
| repulsion between carbohydrate units enabling the molecule to |
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Definition
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Term
| perform its function as lubrication in joint synovial fluids. |
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Definition
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Term
| Hyaluronidase Enzyme or Spreading factor: |
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Definition
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Term
| @ It is the enzyme that hydrolyzes hyaluronic acid. |
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Definition
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Term
| O It is present in sperms to help penetration of the ovum and |
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Definition
|
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Term
|
Definition
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Term
| @ It is present in some virulent strains of bacteria that are able to |
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Definition
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Term
| spread through infected wounds. . |
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Definition
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Term
| 0 It is present also in snake and scorpion venom. |
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Definition
|
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Term
| @ It is used in medicine to treat fibrosis and to dissolve mucus. |
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Definition
|
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Term
| Acidic Nitrogenous Heteropolysaccharides: |
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Definition
|
|
Term
| Sulfated Mucopolysaccharides |
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Definition
|
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Term
|
Definition
|
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Term
| a It is formed of sulfated N-acetyl-galactosamine and glucuronic |
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Definition
|
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Term
|
Definition
|
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Term
| 4 Present in cornea of the eye |
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Definition
| tendons, ligaments, bones, |
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Term
| cartilage and connective tissue matrix. |
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Definition
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Definition
| form incompressible substances by means of |
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Term
| their ionizable OH and sulfate groups |
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Definition
| creating negative charges |
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| leading to repulsion between the molecules. |
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Definition
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Definition
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Definition
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Definition
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Term
| Acidic Nitrogenous Heteropolysaccharides: = |
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Definition
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Definition
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Term
| Sulfated Mucopolysaccharides Deep Ven Thrombosia |
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Definition
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Definition
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Term
| * It is formed of a long repeat of sulfated a-glucosamine and sulfated |
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Definition
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Definition
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| * Biomedical significance: idee |
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Definition
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Term
| 1. It is an anticoagulant produced by mast cells and prevents |
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Definition
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Term
| intravascular clotting. Therefore |
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Definition
| it is used in cases of increased |
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Term
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Definition
| e.g deep venous thrombosis. |
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Term
| 2. It binds to and liberates lipoprotein lipase enzyme to clear the |
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Definition
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Term
| turbid plasma from the absorbed lipids after meals. |
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Definition
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Term
| 3. It participates in cell-cell and cell-matrix interaction |
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Definition
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Definition
| apoptosis and differentiation. uss e |
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