Using the Haworth projection, draw the furanose ring that would form between the C5 hydroxyl group and the ketone at C2 for the molecule shown.

Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids

Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition

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Mullins 1st Edition

Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids

문제 15

26장, 문제 15

Using the Haworth projection, draw the furanose ring that would form between the C₅ hydroxyl group and the ketone at C₂ for the molecule shown.

검증된 단계별 안내

Identify the functional groups involved in the ring formation. The C5 hydroxyl group (OH) will react with the ketone group at C2 to form a furanose ring.

Understand that a furanose ring is a five-membered ring structure. In this case, the ring will include the oxygen from the C5 hydroxyl group, the carbon atoms C2, C3, C4, and C5.

To draw the Haworth projection, start by sketching a five-membered ring with an oxygen atom at the top right corner. This oxygen comes from the C5 hydroxyl group.

Place the carbon atoms in the ring. C2 will be to the right of the oxygen, C3 at the bottom right, C4 at the bottom left, and C5 to the left of the oxygen.

Add the substituents to the ring. The C2 carbon will have a hydroxyl group pointing down (since it was originally a ketone), C3 and C4 will have hydroxyl groups pointing up, and C5 will have a CH2OH group pointing up. Ensure the stereochemistry is consistent with the original Fischer projection.

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Haworth Projection

The Haworth projection is a way of representing cyclic sugars in a two-dimensional format that illustrates the cyclic structure of monosaccharides. It shows the orientation of the hydroxyl groups and other substituents around the ring, making it easier to visualize the three-dimensional conformation of the molecule. This representation is particularly useful for understanding the anomeric carbon and the formation of glycosidic bonds.

Furanose Ring Structure

A furanose ring is a five-membered cyclic structure formed from a monosaccharide, typically when a hydroxyl group reacts with a carbonyl group. In the case of a ketose, such as fructose, the furanose form is created when the hydroxyl group on C₅ reacts with the ketone at C₂. This structure is significant in biochemistry as it influences the reactivity and properties of sugars.

Anomeric Carbon

The anomeric carbon is the carbon atom in a sugar that was originally part of the carbonyl group (aldehyde or ketone) and becomes a new chiral center upon cyclization. In the context of furanose formation, the anomeric carbon determines the alpha or beta configuration of the sugar, which affects its biological activity and interactions. Understanding the anomeric carbon is crucial for predicting the behavior of carbohydrates in biochemical processes.