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Ch.6 Carbohydrates Life's Sweet Molecules
Frost - General, Organic and Biological Chemistry 4th Edition
Frost4th EditionGeneral, Organic and Biological ChemistryISBN: 9780134988696Not the one you use?Change textbook
Chapter 3, Problem 79

Isomaltose, a disaccharide formed during caramelization in cooking, contains two glucose units bonded ⍺(1→6). Draw the structure of isomaltose.

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1
Understand the structure of glucose: Glucose is a monosaccharide with the molecular formula C₆H₁₂O₆. It has a six-membered ring structure (a pyranose ring) with hydroxyl (-OH) groups attached to specific carbons.
Learn about the α (1→6) glycosidic bond: This bond connects the anomeric carbon (C1) of one glucose molecule in the alpha configuration to the C6 carbon of another glucose molecule. The alpha configuration means the -OH group on the anomeric carbon is oriented downward relative to the ring.
Draw the first glucose unit: Start with the pyranose ring structure of glucose. Label the carbons from C1 to C6, ensuring the -OH group on C1 is in the alpha position (downward). Include the hydroxyl groups on the other carbons in their correct positions.
Draw the second glucose unit: Create another pyranose ring structure for glucose. Label the carbons from C1 to C6, ensuring the hydroxyl groups are correctly positioned. The C6 carbon will be the site of attachment to the first glucose unit.
Connect the two glucose units: Form the α (1→6) glycosidic bond by linking the C1 of the first glucose unit to the C6 of the second glucose unit. Ensure the bond orientation reflects the alpha configuration. Add any remaining hydroxyl groups and hydrogens to complete the structure of isomaltose.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Disaccharides

Disaccharides are carbohydrates composed of two monosaccharide units linked by a glycosidic bond. They are formed through a dehydration reaction, where a water molecule is released. Common examples include sucrose, lactose, and isomaltose. Understanding disaccharides is essential for analyzing their structural and functional properties in biological and culinary contexts.
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Glycosidic Bond

A glycosidic bond is a type of covalent bond that connects two monosaccharides in a carbohydrate. In the case of isomaltose, the bond is specifically an α (1→6) linkage, indicating the orientation and position of the bond between the glucose units. This bond plays a crucial role in determining the properties and digestibility of the disaccharide.
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Caramelization

Caramelization is a complex chemical process that occurs when sugars are heated, leading to the formation of new flavors, colors, and compounds. During this process, disaccharides like isomaltose can form as intermediate products. Understanding caramelization is important for culinary applications, as it affects the taste and texture of various foods.