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Ch.6 Carbohydrates–Life’s Sweet Molecules
Chapter 3, Problem 6.11a

Identify the following monosaccharides as the d- or the l-isomer:


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1
Identify the chiral center in the monosaccharide structure. This is typically the carbon atom that is bonded to four different groups.
Locate the hydroxyl group (-OH) attached to the chiral center that is farthest from the carbonyl group (C=O) in the structure.
Determine the orientation of the hydroxyl group on the chiral center. If the hydroxyl group is on the right side in a Fischer projection, it is a D-isomer. If it is on the left side, it is an L-isomer.
Use the Fischer projection to visualize the molecule in a two-dimensional form, which helps in identifying the orientation of the hydroxyl group.
Conclude whether the monosaccharide is a D-isomer or an L-isomer based on the position of the hydroxyl group on the chiral center farthest from the carbonyl group.

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Key Concepts

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

Monosaccharides

Monosaccharides are the simplest form of carbohydrates, consisting of single sugar molecules like glucose and fructose. They serve as the building blocks for more complex carbohydrates and are crucial for energy production in living organisms. Understanding their structure and classification is essential for identifying their isomeric forms.
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D- and L- Isomers

D- and L- isomers refer to the two enantiomers of monosaccharides based on the orientation of the hydroxyl group (-OH) on the chiral carbon furthest from the aldehyde or ketone group. The 'D' designation indicates that the hydroxyl group is on the right in a Fischer projection, while 'L' indicates it is on the left. This classification is vital for understanding the biochemical behavior of sugars.
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Fischer Projection

The Fischer projection is a two-dimensional representation of a molecule that illustrates the arrangement of atoms and functional groups. It is particularly useful for visualizing the stereochemistry of carbohydrates, allowing for easy identification of D- and L- isomers. Mastery of this projection is important for accurately determining the isomeric forms of monosaccharides.
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Fischer Projections Example 1