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Biochemistry

🧬biochemistry review

4.1 Monosaccharides and Disaccharides

Last Updated on August 9, 2024

Carbohydrates are essential molecules in biology, with monosaccharides and disaccharides playing crucial roles. These simple sugars serve as energy sources and building blocks for more complex structures, forming the foundation of carbohydrate chemistry.

Understanding the structure, classification, and properties of mono- and disaccharides is key to grasping their functions in living organisms. From glucose's role as a primary energy source to the importance of glycosidic bonds in disaccharide formation, these concepts are fundamental to biochemistry.

Monosaccharides

Structure and Classification of Simple Sugars

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  • Monosaccharides consist of single sugar units, forming the building blocks of carbohydrates
  • Classified based on the number of carbon atoms (trioses, tetroses, pentoses, hexoses)
  • Contain multiple hydroxyl groups (-OH) and one carbonyl group (C=O)
  • Exist in two forms: aldoses (aldehyde group) and ketoses (ketone group)
  • Glucose serves as the primary energy source for living organisms, featuring a six-carbon aldose structure
  • Fructose occurs naturally in fruits and honey, characterized by a six-carbon ketose structure
  • Galactose plays a crucial role in lactose formation, differing from glucose only in the orientation of one hydroxyl group

Structural Variations and Isomers

  • Anomers represent two forms of a monosaccharide that differ in the configuration of the hydroxyl group at the anomeric carbon
  • Alpha (α) and beta (β) anomers interconvert through a process called mutarotation
  • Epimers describe two monosaccharides that differ in the configuration of only one specific carbon atom
  • Glucose and mannose are epimers, differing at the C-2 position
  • Glucose and galactose are epimers, differing at the C-4 position

Chemical Properties and Reactions

  • Reducing sugars possess a free aldehyde or ketone group, capable of acting as reducing agents
  • All monosaccharides and most disaccharides (except sucrose) are reducing sugars
  • Reducing sugars react with Benedict's or Fehling's solutions, producing a characteristic color change
  • Undergo various reactions including oxidation, reduction, and formation of glycosides
  • Monosaccharides can form cyclic structures through intramolecular reactions between the carbonyl group and a hydroxyl group

Disaccharides

Formation and Structure of Disaccharides

  • Disaccharides form when two monosaccharides join through a glycosidic bond
  • Glycosidic bonds result from a condensation reaction between the anomeric carbon of one sugar and a hydroxyl group of another
  • The bond type (α or β) and the carbons involved determine the disaccharide's properties
  • Maltose consists of two glucose units linked by an α(1→4) glycosidic bond
  • Lactose comprises glucose and galactose connected by a β(1→4) glycosidic bond
  • Sucrose contains glucose and fructose joined by an α(1→2) glycosidic bond

Biological Significance and Metabolism

  • Maltose serves as an intermediate in starch digestion, broken down by the enzyme maltase
  • Lactose functions as the primary sugar in mammalian milk, hydrolyzed by lactase in the small intestine
  • Sucrose acts as a common table sugar, cleaved by sucrase into its component monosaccharides
  • Disaccharides undergo hydrolysis in the digestive system, breaking down into their constituent monosaccharides
  • Enzymes specific to each disaccharide catalyze the hydrolysis reactions (maltase, lactase, sucrase)

Chemical Properties and Industrial Applications

  • Maltose and lactose are reducing sugars due to their free anomeric carbon
  • Sucrose is a non-reducing sugar because its glycosidic bond involves both anomeric carbons
  • Disaccharides exhibit different levels of sweetness (sucrose > maltose > lactose)
  • Used in various industries including food processing, brewing, and pharmaceuticals
  • Lactose intolerance results from insufficient lactase production, leading to digestive issues when consuming dairy products