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Ch.6 Carbohydrates–Life’s Sweet Molecules
Chapter 3, Problem 6.79

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

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1
Identify the structure of a glucose molecule. Glucose is a six-carbon sugar with the chemical formula C₆H₁₂O₆. It has a ring structure with five carbon atoms and one oxygen atom forming a hexagonal shape.
Understand the glycosidic bond. In isomaltose, the two glucose units are linked by an α (1→6) glycosidic bond. This means the bond is formed between the first carbon (C1) of one glucose and the sixth carbon (C6) of the other glucose.
Draw the first glucose unit. Start by drawing the hexagonal ring with the oxygen at the top right. Number the carbons clockwise starting from the carbon to the right of the oxygen.
Draw the second glucose unit. Similarly, draw another hexagonal ring for the second glucose molecule. Number the carbons in the same manner.
Connect the two glucose units. Form the α (1→6) glycosidic bond by connecting the C1 of the first glucose to the C6 of the second glucose. Ensure the bond is drawn below the plane of the ring to indicate the alpha configuration.

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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. Isomaltose, specifically, consists of two glucose molecules connected by an α (1→6) bond, which influences its properties and how it is metabolized in the body.
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Glycosidic Bonds

Glycosidic bonds are covalent linkages that connect carbohydrate molecules. In the case of isomaltose, the bond is an α (1→6) glycosidic bond, indicating the specific orientation of the bond between the glucose units. This type of bond affects the structure and digestibility of the sugar, distinguishing it from other disaccharides like sucrose or lactose.
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Caramelization

Caramelization is a complex chemical process that occurs when sugars are heated, leading to the formation of new compounds and flavors. During this process, disaccharides like isomaltose can form as intermediate products. Understanding caramelization is essential for recognizing how isomaltose is produced in cooking and its role in the flavor and color of caramelized foods.