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    Carbohydrates

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    Kizito Shafic
    Carbohydrates are biologically important compounds that provide energy, supply carbon for cell components, serve as stored energy, and form cell structures. They are classified based on their structure into monosaccharides, disaccharides, oligosaccharides, and polysaccharides. Monosaccharides are the simplest carbohydrates and include sugars like glucose and fructose. Many carbohydrates are chiral molecules that have non-superimposable mirror images and can rotate polarized light, making them optically active.

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    Carbohydrates

    Uploaded by

    Kizito Shafic
    16 views3 pages
    Carbohydrates are biologically important compounds that provide energy, supply carbon for cell components, serve as stored energy, and form cell structures. They are classified based on their structure into monosaccharides, disaccharides, oligosaccharides, and polysaccharides. Monosaccharides are the simplest carbohydrates and include sugars like glucose and fructose. Many carbohydrates are chiral molecules that have non-superimposable mirror images and can rotate polarized light, making them optically active.

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    3. Carbohydrates

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    Carbohydrates are biologically important compounds that provide energy, supply carbon for cell components, serve as stored energy, and form cell structures. They are classified based on their structure into monosaccharides, disaccharides, oligosaccharides, and polysaccharides. Monosaccharides are the simplest carbohydrates and include sugars like glucose and fructose. Many carbohydrates are chiral molecules that have non-superimposable mirror images and can rotate polarized light, making them optically active.

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    © All Rights Reserved
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    16 views3 pages

    Carbohydrates

    Uploaded by

    Kizito Shafic
    Carbohydrates are biologically important compounds that provide energy, supply carbon for cell components, serve as stored energy, and form cell structures. They are classified based on their structure into monosaccharides, disaccharides, oligosaccharides, and polysaccharides. Monosaccharides are the simplest carbohydrates and include sugars like glucose and fructose. Many carbohydrates are chiral molecules that have non-superimposable mirror images and can rotate polarized light, making them optically active.

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    CARBOHYDRATES

    Carbohydrates are compounds of tremendous biological importance:


    – they provide energy through oxidation
    – they supply carbon for the synthesis of cell components
    – they serve as a form of stored chemical energy
    – they form part of the structures of some cells and tissues

    Carbohydrates
    • Carbohydrates are polyhydroxy aldehydes or ketones, or substances that yield such compounds on
    hydrolysis.

    Classes of Carbohydrates
    • Monosaccharides contain a single polyhydroxy aldehyde or ketone unit (saccharo is Greek for “sugar”)
    (e.g., glucose, fructose).
    • Disaccharides consist of two monosaccharide units linked together by a covalent bond (e.g., sucrose).
    • Oligosaccharides contain from 3 to 10 monosaccharide units (e.g., raffinose).
    • Polysaccharides contain very long chains of hundreds or thousands of monosaccharide units, which
    may be either in straight or branched chains (e.g., cellulose, glycogen, starch).

    Stereoisomers
    • Glyceraldehyde, the simplest carbohydrate, exists in two isomeric forms that are mirror images of each
    other:
    • These forms are stereoisomers of each other.

    • Glyceraldehyde is a chiral molecule — it cannot be superimposed on its mirror image. The two mirror
    image forms of glyceraldehyde are enantiomers of each other.

    Chiral Carbons
    • Chiral molecules have the same relationship to each other that your left and right hands have when
    reflected in a mirror.
    • Achiral objects can be superimposed on the mirror images — for example, drinking glasses, spheres, and
    cubes.
    • Any carbon atom which is connected to four different groups will be chiral and will have two non-
    superimposable mirror images; it is a chiral carbon or a center of chirality. – if any of the two groups
    on the carbon are the same, the carbon atom cannot be chiral.
    • Many organic compounds, including carbohydrates, contain more than one chiral carbon.

    What’s So Great About Chiral Molecules?


    • Molecules which are enantiomers of each other have the same physical properties (melting point, boiling
    point, index of refraction, etc.) but not their interaction with polarized light.
    • Polarized light vibrates only in one plane; it results from passing light through a polarizing filter.

    Optical Activity
    • A levorotatory (–) substance rotates polarized light to the left. [E.g., l-glucose; (-)-glucose]
    • A dextrorotatory (+) substance rotates polarized light to the right. [E.g., d-glucose; (+)-glucose]
    • Molecules which rotate the plane of polarized light are optically active.
    • Most biologically important molecules are chiral, and hence are optically active. Often, living systems
    contain only one of all the possible stereochemical forms of a compound. In some cases, one form of a
    molecule is beneficial, and the enantiomer is a poison (e.g., thalidomide).

    Monosaccharides
    Classification of Monosaccharides
    • The monosaccharides are the simplest of the carbohydrates, since they contain only one polyhydroxy
    aldehyde or ketone unit.
    • Monosaccharides are classified according to the number of carbon atoms they contain:

    • The presence of an aldehyde is indicated by the prefix aldo- and a ketone by the prefix keto-.
    Classification of Monosaccharides
    • Thus, glucose is an aldohexose (aldehyde + 6 Cs) and ribulose is a ketopentose (ketone + 5 Cs)

    Physical Properties of Monosaccharides


    • Most monosaccharides have a sweet taste (fructose is sweetest; 73% sweeter than sucrose).
    • They are solids at room temperature.
    • They are extremely soluble in water.

    Chemical Properties of Monosaccharides


    • Monosaccharides do not usually exist in solution in their “open-chain” forms: an alcohol group can add
    into the carbonyl group in the same molecule to form a pyranose ring containing a stable cyclic
    hemiacetal or hemiketal.

    Oxidation of Monosaccharides
    • Aldehydes and ketones that have an OH group on the carbon next to the carbonyl group react with a
    basic solution of Cu2+ (Benedict’s reagent) to form a red-orange precipitate of copper(I) oxide
    (Cu2O).
    • Sugars that undergo this reaction are called reducing sugars. (All of the monosaccharides are reducing
    sugars.)
    • In the pyranose form of glucose, carbon-1 is chiral, and thus two stereoisomers are possible: one in
    which the OH group points down (α-hydroxy group) and one in which the OH group points up (β-
    hydroxy group). These forms are anomers of each other, and carbon-1 is called the anomeric
    carbon.

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