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    Carbohydrates: Chapter 7 (Part I)

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    Omer Kareem
    Carbohydrates are the most abundant biological compounds and are involved in energy storage, structure, and transport. They include monosaccharides like glucose and fructose, disaccharides like sucrose and lactose formed from two monosaccharides linked by glycosidic bonds, and polysaccharides composed of long chains of monosaccharides like starch, glycogen, and cellulose. Glycosidic bonds form between the anomeric carbon of one sugar and the hydroxyl group of another, and are named based on the linked carbons and configuration of the anomeric hydroxyl group. Common structural polysaccharides include cellulose, an unbranched polymer of glucose, and glycogen, a branched polymer of glucose residues in

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    Carbohydrates: Chapter 7 (Part I)

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    Omer Kareem
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    Carbohydrates are the most abundant biological compounds and are involved in energy storage, structure, and transport. They include monosaccharides like glucose and fructose, disaccharides like sucrose and lactose formed from two monosaccharides linked by glycosidic bonds, and polysaccharides composed of long chains of monosaccharides like starch, glycogen, and cellulose. Glycosidic bonds form between the anomeric carbon of one sugar and the hydroxyl group of another, and are named based on the linked carbons and configuration of the anomeric hydroxyl group. Common structural polysaccharides include cellulose, an unbranched polymer of glucose, and glycogen, a branched polymer of glucose residues in

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    Carbohydrates are the most abundant biological compounds and are involved in energy storage, structure, and transport. They include monosaccharides like glucose and fructose, disaccharides like sucrose and lactose formed from two monosaccharides linked by glycosidic bonds, and polysaccharides composed of long chains of monosaccharides like starch, glycogen, and cellulose. Glycosidic bonds form between the anomeric carbon of one sugar and the hydroxyl group of another, and are named based on the linked carbons and configuration of the anomeric hydroxyl group. Common structural polysaccharides include cellulose, an unbranched polymer of glucose, and glycogen, a branched polymer of glucose residues in

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    41 views16 pages

    Carbohydrates: Chapter 7 (Part I)

    Uploaded by

    Omer Kareem
    Carbohydrates are the most abundant biological compounds and are involved in energy storage, structure, and transport. They include monosaccharides like glucose and fructose, disaccharides like sucrose and lactose formed from two monosaccharides linked by glycosidic bonds, and polysaccharides composed of long chains of monosaccharides like starch, glycogen, and cellulose. Glycosidic bonds form between the anomeric carbon of one sugar and the hydroxyl group of another, and are named based on the linked carbons and configuration of the anomeric hydroxyl group. Common structural polysaccharides include cellulose, an unbranched polymer of glucose, and glycogen, a branched polymer of glucose residues in

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    of 16

    Carbohydrates

    Chapter 7 (Part I)
    Carbohydrates and Glycobiology

    • The most abundant biological compounds

    • Structurally related but have a different chemical properties

    • Involved in the storage and transport of energy (Starch, Glycogen)

    • As structural component (Cellulose in plants & Chitin in animals)

    • Divided into: monosaccharides , disaccharides & polysaccharides

    • General formula (CH2O)n

    • The term came from the hydrate (H2O) of carbon (C)

    • In all sugars, n-1 of the carbons has a hydroxyl (OH) group and the C-1 carbon has a carbonyl
    (C=O) group. The location of the carbonyl group and the orientation of the hydroxyl groups
    determine the type of sugar
    Classification and structure of carbohydrates

     Carbohydrates with:
     carbonyl group at the end (an aldehyde group) then it is an aldose (e.g. glucose)
     Carbonyl group in the middle (a ketone group) then it is a ketose (e.g. fructose)
    Classification of carbohydrates (Monosaccharides)

    • Some monosaccharides found in humans, classified according to the number of carbons they
    contain
    Monosaccharides

    Monosaccharides

    • Glucose is more often found in a ring form in solution

    • The Orientation of the OH group on the C-1 carbon can be either in the alpha (below the plane of
    the ring) or beta (above the plane of the ring) position
    Monosaccharides

    Glucose
    Glycosides

    • Monosaccarides can be linked by glycosidic bonds to create larger structures


    (glycosides)

    • Glycosides are formed by enzymes known as glycosyltransferases that use nucleotide


    sugars such as UDP-glucose (Uridine diphosphate glucose) as substrates.

    • Disaccharides: 2 monosaccharides (e.g. Sucrose, maltose, lactose)

    • Oligosaccharides: 3-10 monosaccharides

    • Polysaccharides or glycans: more than 10 monosaccharides


    Glycosides

    •Glycosidic bonds are covalent chemical bonds that hold together a glycoside. A glycoside is simply
    a ring-shaped sugar molecule that is attached to another molecule. The sugar ring may be either a 5-
    membered ring or a 6-membered ring, and the other molecule can be - and often is - another sugar

    •A glycosidic bond forms by a condensation reaction, which means that one water molecule is
    produced during formation of a glycoside. The reverse reaction, the breakage of a glycosidic bond, is
    a hydrolysis reaction. One water molecule is used up in the reverse reaction.
    Glycosyl
    Glycosides

    • The condensation reaction occurs when an alcohol group, or OH, from a molecule attacks
    the anomeric carbon of a sugar. The anomeric carbon is the central carbon of a hemiacetal. That
    is, the carbon has single bonds to two oxygen atoms

    • One of the oxygen atoms is part of the sugar ring, and the other is an OH group. When the alcohol
    attacks the anomeric carbon, the OH group bonded to that carbon is replaced by the O of the
    alcohol, and the H of the alcohol is removed. Both an H and an OH are removed from the original
    molecules during the reaction. Together they make H2O, or water.

    • The result of a glycosidic bond is a sugar molecule linked to another molecule via an ether group.
    An ether is an oxygen atom bonded to two carbon atoms, which is relatively unreactive compared to
    other chemical groups, such as alcohols. Therefore, glycosides tend to be more stable than free
    sugars
    Glycosidic bond Hemiacetal
    Disaccharides

    • Maltose:

    • is a disaccharide with an α(1 → 4) glycosidic link between C1 - C4 OH of 2 glucoses

    • Sucrose:

    • common table sugar is composed of glucose and fructose through an α–(1,2)


    glycosidic bond

    • Lactose:

    • is found exclusively in the milk of mammals and consists of galactose and glucose in
    a β–(1,4) glycosidic bond

    • Lactase enzyme breaks down lactose to glucose and galactose. Many adult
    individuals stop synthesizing lactase enzyme  lactose-intolerant
    Disaccharides

    • Glycosidic bonds between sugars are named according to the numbers of the connected carbons,
    and also with regard to the position of the anomeric hydroxyl group of the sugar involved in the
    bond. If this anomeric hydroxyl is in the α configuration, the linkage is an α-bond. If it is in the β
    configuration, the linkage is a β-bond. Lactose, for example, is synthesized by forming a glycosidic
    bond between carbon 1 of β-galactose and carbon 4 of glucose. The linkage is, therefore, a
    β(1→4) glycosidic bond
    Disaccharides

    Maltose

    Sucrose

    Lactose
    Polysaccharides

    • Polysaccharides consist of many monosaccharide units (usually glucose monomers) linked


    together to form long chains

    • Polysaccharides composed of a single monosaccharide are termed homopolysaccharides

    • Polysaccharides composed of more than one type of monosaccharide are


    termed heteropolysaccharides

    • Used as a form of storage of energy and also for structural roles (e.g. starch, glycogen, cellulose)

    • Cellulose – plays an important structural role in plants; one of the most abundant molecules on
    earth.. it is an unbranched polymer of glucose in β-(1→4) linkage

    • Glycogen: α-1,4-glycosidic bonded branched polymer of glucose residues


    Polysaccharides

    Glycogen

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