Textbook Question
D-Fructose can also form a six-membered ring. Draw the β anomer of D-fructose in the six-membered ring form.
Ch.6 Carbohydrates Life's Sweet Molecules
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696
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Table of contents
- Ch.4 Introduction to Organic Compounds75
- Ch.5 Chemical Reactions19
- Ch.6 Carbohydrates Life's Sweet Molecules62
- Ch.7 States of Matter and Their Attractive Forces8
- Ch.8 Solution Chemistry Sugar and Water Do Mix4
- Ch.10 Proteins Workers of the Cell89
- Ch.11 Nucleic Acids Big Molecules with a Big Role69
- Ch.12 Food as Fuel An Overview of Metabolism65
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696Not the one you use?Change textbook
Chapter 3, Problem 93
Trehalose is a naturally occurring disaccharide used in cosmetics because of its ability to retain moisture. The formal name of trehalose is glucose α, α(1→1) glucose. Draw the structure of trehalose. Is it a reducing or nonreducing sugar?
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Understand the structure of trehalose: Trehalose is a disaccharide composed of two glucose molecules linked by an α, α (1→1) glycosidic bond. This means the anomeric carbons of both glucose units are involved in the bond.
Draw the structure of trehalose: Start by sketching two glucose molecules. Identify the anomeric carbon (carbon 1) in each glucose unit, and connect them via an α, α (1→1) glycosidic bond. Ensure both glucose units are in their cyclic (pyranose) form.
Determine if trehalose is a reducing or nonreducing sugar: A sugar is reducing if it has a free anomeric carbon that can open to form an aldehyde group. Since both anomeric carbons in trehalose are involved in the glycosidic bond, neither is free.
Conclude trehalose's reducing property: Based on the structure, trehalose is a nonreducing sugar because it lacks a free anomeric carbon.
Review the significance: Trehalose's nonreducing nature contributes to its stability and ability to retain moisture, making it useful in cosmetics and other applications.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Trehalose Structure
Trehalose is a disaccharide composed of two glucose molecules linked by an α,α (1→1) glycosidic bond. This unique linkage means that both anomeric carbons of the glucose units are involved in the bond, resulting in a specific three-dimensional structure that influences its properties, including its ability to retain moisture.
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Reducing vs. Nonreducing Sugars
Reducing sugars are carbohydrates that can donate electrons to other molecules, typically due to the presence of a free anomeric carbon. In contrast, nonreducing sugars, like trehalose, have both anomeric carbons involved in glycosidic bonds, preventing them from acting as reducing agents. This characteristic is crucial for understanding their chemical behavior and applications.
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Moisture Retention in Cosmetics
Trehalose is valued in cosmetics for its hygroscopic properties, meaning it can attract and hold water molecules. This ability helps to maintain skin hydration and improve the texture of cosmetic products. Understanding the role of trehalose in moisture retention is essential for formulating effective skincare solutions.
Related Practice
Textbook Question
How much energy is produced if a person eats 50 g of digestible carbohydrate (not fiber) in a day? In this case, what percent of a 2200 Calorie diet would be digestible carbohydrate? Recall that carbohydrates provide four Calories of energy per gram consumed.
Textbook Question
Which of the components in starch is more likely to be broken down more quickly in plants, amylose or amylopectin? Why?