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Biomolecules · Bioelements and biomolecules

Carbohydrates

Before a big cross-country meet, lots of high school runners eat a plate of pasta the night before, taking in a store of glucose that the plant packaged as starch and that their body will later store as glycogen. In this section you'll go from the simplest sugar molecule to the polymer and see how the same chemical unit —a monosaccharide— can serve as an immediate fuel or as a structural material, depending on how it is bonded and folded.

Monosaccharides: the basic unit

If you dissolve a spoonful of glucose in water and add digestive enzymes or mild acid, the molecule does not break down into smaller carbohydrates: you have reached the limit of the sugars. What chemical features define this basic unit, and how does its structure determine the function it performs?

Monosaccharides are the cell's quick fuel: cells break down glucose to make ATP. They are also the building blocks (monomers) of larger carbohydrates. Glucose and fructose are two common examples. Fructose is the sugar in fruit and honey.

Fischer straight-chain formulae of glucose (aldehyde at C1) and fructose (ketone at C2): both with six carbons and the formula C₆H₁₂O₆. glucose (straight-chain form) 1 2 3 4 5 6 CHO aldehyde H HO H H OH H OH OH CH₂OH fructose (straight-chain form) 1 2 3 4 5 6 CH₂OH O ketone HO H H H OH OH CH₂OH both: C₆H₁₂O₆
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What is a monosaccharide? Give two examples and state the main function of monosaccharides in the cell.

What is a monosaccharide? Give two examples and state the main function of monosaccharides in the cell.

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Disaccharides: the glycosidic bond

Formation of sucrose: α-D-glucose and β-D-fructose, in Haworth projection, are joined through the OH groups of their anomeric carbons (C1 and C2) by an O-glycosidic bond. In condensation a water molecule is released and in hydrolysis one is consumed. O CH₂OH HO OH OH OH 1 α-D-glucose + O HO CH₂OH OH OH CH₂OH 2 β-D-fructose condensation (H₂O released) hydrolysis (H₂O consumed) O CH₂OH HO OH OH 1 O O CH₂OH OH OH CH₂OH 2 O-glycosidic bond α(1→2)β + H₂O sucrose
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Classify the following carbohydrates as monosaccharides, disaccharides, or polysaccharides: glucose, sucrose, starch, fructose, lactose, and cellulose.

Classify the following carbohydrates as monosaccharides, disaccharides, or polysaccharides: glucose, sucrose, starch, fructose, lactose, and cellulose.

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Sucrose is formed by the joining of a glucose molecule and a fructose molecule. What type of bond is formed between the two monosaccharides, what is the reaction that…

Sucrose is formed by the joining of a glucose molecule and a fructose molecule. What type of bond is formed between the two monosaccharides, what is the reaction that forms it called, and what molecule is released during it?

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Polysaccharides: energy storage and structure

A cotton T-shirt (Texas grows a lot of cotton) and a spoonful of flour are made of exactly the same monomer —D-glucose—, yet the T-shirt neither dissolves nor can we digest it, while flour thickens when cooked and nourishes us. How do cells achieve such opposite properties from the same building block?

Comparison between starch or glycogen, whose glucose units joined by alpha bonds form a chain coiled into a compact storage helix, and cellulose or chitin, whose glucose units joined by beta bonds, with alternate monomers turned through 180 degrees, form straight parallel chains held together by hydrogen bonds. starch / glycogen (α bond) cellulose / chitin (β bond) alternate monomers turned 180° D-glucose (or derivative, chitin) hydrogen bonds coiled chain (helix) storage: compact, accessible straight parallel chains structure: rigid, insoluble

In animals, extra glucose is stored as glycogen, mainly in the liver (which releases glucose to keep blood sugar steady) and in skeletal muscle (fuel for the muscle itself).

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State the biological function of glycogen in animals and in which organs it is mainly stored.

State the biological function of glycogen in animals and in which organs it is mainly stored.

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The diagram shows how the chains of two polysaccharides made exclusively of glucose are arranged. State which corresponds to starch and which to cellulose, explain what…

The diagram shows how the chains of two polysaccharides made exclusively of glucose are arranged. State which corresponds to starch and which to cellulose, explain what difference exists in the bonding of their monomers (α or β bond), and reason how the shape of their chains justifies why one serves as an energy reserve and the other has a structural function.

A B H-bonds
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Carbohydrates in the diet and metabolism

From the plate to the muscle: starch in the intestinal lumen is hydrolyzed to glucose, which crosses the intestinal wall, enters the blood and is transported to the muscle fiber, where ATP is obtained or it is stored as glycogen. intestinal lumen starch hydrolysis glucose intestinal wall absorption blood transport muscle fiber ATP glycogen

Back to the start: The runner eats pasta because its starch has $\alpha(1\to 4)$ bonds that our enzymes readily hydrolyze into free glucose; this passes into the blood and is stored in the muscle as glycogen, a compact reserve ready to release fuel quickly during the race.

Pentoses, isomerism and recognizing structures

Ribose is a pentose found in RNA; 2-deoxyribose, found in DNA, has H instead of OH on carbon 2. Glucose, galactose and fructose are hexoses. Glucose and fructose differ in their carbonyl group (aldose/ketose); glucose and galactose differ in the configuration of one asymmetric carbon (epimers).

Top, furanose rings of ribose (OH at C2, RNA) and 2-deoxyribose (H at C2, DNA); bottom, open chains of glucose (aldehyde at C1) and fructose (ketone at C2). Ribose (5 C) · RNA 2-deoxyribose (5 C) · DNA Glucose (6 C): aldohexose Fructose (6 C): ketohexose O CH₂OH OH OH OH C2 O CH₂OH OH H OH C2 CHO OH OH OH OH CH₂OH CH₂OH O OH OH OH CH₂OH

Summary

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