Carbohydrates: Basic Composition and Classification

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30 Questions

What is the basic composition of carbohydrates?

(CH2O)n

What is a monosaccharide?

A simple sugar with multiple OH groups

What is the chemical formula for glucose?

C6H12O6

Which sugar has the highest relative sweetness?

Fructose

What type of group do aldoses have at one end?

Aldehyde group

What is the simplest of the aldoses?

D-glyceraldehyde

Which term describes the varying sweetness of different monosaccharides?

Arrangement differences

What does it mean when a sugar solution is described as dextrorotatory?

It turns the plane of polarized light to the right

What type of bond is formed when the anomeric hydroxyl and another compound join together?

Glycosidic bond

Which sugar derivative has an amino group that substitutes for a hydroxyl group?

Glucosamine

What type of form does methyl-D-glucoside take when reacting with methanol?

$\alpha$-D-glucopyranose

What accounts for the differences in sweetness among glucose, fructose, and galactose?

Carbon chain length

What type of glycosidic bond holds together two glucose units in maltose?

α(1→4)

Which disaccharide is composed of galactose & glucose with a β(1→4) glycosidic linkage?

Lactose

What is the product of cellulose breakdown that is the equivalent β anomer of maltose?

Cellobiose

Which disaccharide has a glycosidic bond linking the anomeric hydroxyls of glucose & fructose?

Sucrose

What type of glycosidic bond holds together α-D-glucose &β-D-fructose units in sucrose?

(α1→2)

What is the full name of lactose?

β-D-galactopyranosyl-(1→4)α-D-glucopyranose

What is the relationship between two aldotetroses that are stereoisomers and mirror images of each other?

They are enantiomers

What type of reaction occurs when an aldehyde reacts with an alcohol?

Hemiacetal formation

What is the difference between a hemiacetal and a hemiketal?

A hemiacetal is formed from an aldehyde and a hemiketal is formed from a ketone

What are anomers?

Stereoisomers formed when a ring is formed

What is the rule for drawing the highest numbered carbon for D-sugars in Haworth projections?

It is drawn up

What is the relationship between two aldohexoses that differ only in the position of the hydroxyl group on one asymmetric carbon (carbon 4)?

They are epimers

Which sugar is the principal sugar in milk?

Lactose

Which of the following sugars is a non-reducing sugar?

Sucrose

What happens to the rotation of sucrose in solution when it is hydrolyzed?

It changes from dextrorotatory to levorotatory

Which polysaccharide is the most common storage polysaccharide in plants?

Starch

What is the primary polymeric form of glucose storage in plants?

Starch

Which type of amylose is a glucose polymer with α(1→4) linkages?

α-amylose

Study Notes

Carbohydrates (Glycans)

  • General composition: (CH2O)n
  • Classified into four categories: monosaccharides, disaccharides, oligosaccharides, and polysaccharides

Monosaccharides (Simple Sugars)

  • Characteristics:
    • Energy-containing molecules
    • Provide structure
    • Basic building block: (CH2O)n; n = 3, 5, 6
    • Classified by number of carbons and type (aldose or ketose)
  • Examples:
    • Glucose (C6H12O6)
    • Fructose
    • Galactose
    • D-glyceraldehyde (simplest aldose)

Disaccharides

  • Definition: 2 monosaccharides covalently linked
  • Examples:
    • Maltose (α-D-glucose units linked by α(1→4) glycosidic bond)
    • Sucrose (α-D-glucose and β-D-fructose units linked by α(1→2) glycosidic bond)
    • Lactose (β-D-galactose and β-D-glucose units linked by β(1→4) glycosidic bond)

Glycosidic Bonds

  • Formation: anomeric hydroxyl and a hydroxyl of another sugar or compound join together, splitting out water
  • Example: methanol reacts with the anomeric OH on glucose to form methyl glucoside

Sugar Derivatives

  • Amino sugars: an amino group substitutes for a hydroxyl (e.g., glucosamine)
  • Acetylated amino sugars: amino group may be acetylated (e.g., N-acetylglucosamine)

Optical Activity

  • Dextrorotatory (+): sugar solution turns the plane of polarized light to the right
  • Levorotatory (-): sugar solution turns the plane of polarized light to the left
  • Racemic mixture: equimolar mixture of optical isomers has no net rotation

Polysaccharides

  • Definition: polymers consisting of chains of monosaccharide or disaccharide units
  • Examples:
    • Starch (plant storage polysaccharide, composed of amylose and amylopectin)
    • Amylose (glucose polymer with α(1→4) linkages)
    • Amylopectin (glucose polymer with varying lengths and molecular weights)

Miscellaneous

  • Relative sweetness of different sugars:
    • Sucrose: 100
    • Glucose: 74
    • Fructose: 174
    • Lactose: 16
    • Invert Sugar: 126
    • Maltose: 32
    • Galactose: 32
  • Hemiacetal and hemiketal formation: reaction between an aldehyde or ketone and an alcohol to form a hemiacetal or hemiketal, respectively

Learn about the basic composition of carbohydrates (glycans) with the general formula (CH2O)n. Explore the classification of carbohydrates into monosaccharides, disaccharides, oligosaccharides, and polysaccharides based on the number of carbons in the molecules.

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