Biochem Oct. 1st

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Topic 7

Last updated 4:52 PM on 10/31/25
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1
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How can monosaccharides be described?

  • Can be characterized by their chemical structure

    • Pentose: 5 carbon atoms

    • Hexose: 6 carbon atoms

  • D and L Isomers

    • Stereochemistry based on the position of the hydroxyl group on the highest-numbered chiral carbon

    • D-sugar: Hydroxyl group on the right.

    • L-sugar: Hydroxyl group on the left.

<ul><li><p>Can be characterized by their chemical structure</p><ul><li><p>Pentose: 5 carbon atoms</p></li><li><p>Hexose: 6 carbon atoms</p></li></ul></li><li><p>D and L Isomers</p><ul><li><p>Stereochemistry based on the position of the hydroxyl group on the highest-numbered chiral carbon</p></li><li><p>D-sugar: Hydroxyl group on the right.</p></li><li><p>L-sugar: Hydroxyl group on the left.</p></li></ul></li></ul><p></p>
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How do Sugars (Carbohydrates) cyclize?

  • Sugars like glucose tend to cyclize due to nucleophilic attack (O from 5th carbon attacks carbonyl)

  • Results in a stable ring structure typically containing 5 or 6 members (favorably cyclized form)

  • the C=O becomes OH once the hydroxyl group from the 5th carbon bonds to it

<ul><li><p>Sugars like glucose tend to cyclize due to nucleophilic attack (O from 5th carbon attacks carbonyl)</p></li><li><p>Results in a stable ring structure typically containing 5 or 6 members (favorably cyclized form)</p></li></ul><p></p><ul><li><p>the C=O becomes OH once the hydroxyl group from the 5th carbon bonds to it</p></li></ul><p></p>
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What are anomeric carbons and how do we identify them?

  • Identification of the anomeric carbon (carbon with two bonds to oxygen) is crucial for defining alpha (a) and beta (b) forms of sugars

    • Alpha glucose

      • Hydroxyl on the opposite side of the anomeric carbon

      • Vowels (alpha/opposite)

    • Beta glucose

      • Hydroxyl on the same side as the anomeric carbon

      • Consonants (beta/same)

  • (Doesn’t always have to be the farthest from the carbonyl group)

  • (IS SOMETIMES CHIRAL OR ACHIRAL)

<ul><li><p>Identification of the anomeric carbon (carbon with two bonds to oxygen) is crucial for defining alpha (a) and beta (b) forms of sugars</p><ul><li><p>Alpha glucose</p><ul><li><p>Hydroxyl on the opposite side of the anomeric carbon</p></li><li><p>Vowels (alpha/opposite)</p></li></ul></li><li><p>Beta glucose</p><ul><li><p>Hydroxyl on the same side as the anomeric carbon</p></li><li><p>Consonants (beta/same)</p></li></ul></li></ul></li></ul><p></p><ul><li><p>(Doesn’t always have to be the farthest from the carbonyl group)</p></li><li><p>(IS SOMETIMES CHIRAL OR ACHIRAL)</p></li></ul><p></p>
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How do Disaccharides form?

  • Formed when two monosaccharides bond through a glycosidic bond via a condensation reaction

    • Occurs when the hydroxyl group (-OH) on the anomeric carbon of one sugar reacts with an -OH group of another molecule (a water molecules is released)

    • (An O-glycosidic bond)

  • the anomeric carbon that’s forming the glycosidic bond can’t switch between alpha and beta but the other anomeric carbon can

<ul><li><p>Formed when two monosaccharides bond through a glycosidic bond via a <span style="color: red;">condensation</span> reaction</p><ul><li><p>Occurs when the hydroxyl group (-OH) on the anomeric carbon of one sugar reacts with an -OH group of another molecule <span style="color: red;">(a water molecules is released)</span></p></li><li><p>(An O-glycosidic bond)</p></li></ul></li><li><p>the anomeric carbon that’s forming the glycosidic bond can’t switch between alpha and beta but the other anomeric carbon can </p></li></ul><p></p>
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<p>Ex. which is alpha and which is beta?</p>

Ex. which is alpha and which is beta?

  • To determine which form is alpha or beta, identify the anomeric carbon and observe the position of the hydroxyl group; if it is on the opposite side of the anomeric carbon, it is alpha, while if it is on the same side, it is beta

  • (fructose also always makes 5 membered rings)

<ul><li><p>To determine which form is alpha or beta, identify the anomeric carbon and observe the position of the hydroxyl group; if it is on the opposite side of the anomeric carbon, it is alpha, while if it is on the same side, it is beta</p></li><li><p>(fructose also always makes 5 membered rings)</p></li></ul><p></p>
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What are polysaccharides?

  • Polysaccharides are complex carbohydrates formed by the linkage of multiple monosaccharides through glycosidic bonds, serving various structural and energy storage roles in organisms

  • Polysaccharides as energy storage

    • Stored as glycogen in animals and starch in plants, providing a readily available source of energy

    • Glycogen

      • Represented by a structure with glycogenin as a central protein primer molecule, around which glycogen chains are synthesized

  • Polysaccharides as structural molecules

    • Cellulose in plant cell walls

    • Pectin for cell wall in fruits

    • Dietary fibers that humans can’t efficiently digest

      • cellulose, chitin

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What are Oligosaccharides?

  • Protect cells, make them slippery

  • These surface carbohydrates  influence cell-cell recognition, adhesion and provide physical protection