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Magazine Chapter 24: Problem 9
What is the difference in structure between \(\mathrm{D}\) -ribose and 2 -deoxy- D-ribose?
Short Answer
Expert verified
The difference is the absence of an oxygen atom at the second carbon in 2-deoxy-D-ribose.
Step by step solution
01
Understanding the Problem
We need to determine the structural difference between two molecules: \( \mathrm{D} \)-ribose and 2-deoxy-\( \mathrm{D} \)-ribose. Both are sugars, and their difference involves a particular oxygen atom.
02
Structure of D-ribose
\( \mathrm{D} \)-ribose is a pentose, which means it is a five-carbon sugar. Its general structure includes a hydroxyl group (\(-\mathrm{OH}\)) attached to each carbon atom except one, which forms the aldehyde functional group at the first carbon.
03
Structure of 2-deoxy-D-ribose
2-deoxy-\( \mathrm{D} \)-ribose is also a five-carbon sugar but with a crucial difference: it lacks an oxygen atom at the second carbon. Thus, instead of a hydroxyl group, only a hydrogen is attached to the second carbon atom.
04
Identifying the Structural Difference
The primary structural difference between \( \mathrm{D} \)-ribose and 2-deoxy-\( \mathrm{D} \)-ribose is the absence of a hydroxyl group at the second carbon position in 2-deoxy-\( \mathrm{D} \)-ribose, where a hydrogen replaces it.
05
Verifying the Structural Difference
In \( \mathrm{D} \)-ribose, the second carbon is bonded to a hydroxyl group. In 2-deoxy-\( \mathrm{D} \)-ribose, this hydroxyl group is absent, signifying the compound is 'deoxy' at that position.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
D-ribose
D-ribose is a type of sugar known for being part of the backbone of RNA, an essential molecule in biological systems. It is a pentose sugar, which means it contains five carbon atoms. These carbons are numbered from 1 to 5, starting from the end closest to the aldehyde functional group. Each carbon atom in D-ribose has a specific structural configuration:
- The first carbon carries an aldehyde group, making it an aldose sugar.
- The second, third, fourth, and fifth carbons each have a hydroxyl group (\(-\mathrm{OH}\)) attached.
2-deoxy-D-ribose
2-deoxy-D-ribose is a modified version of D-ribose, and it's a critical component of DNA. "Deoxy" refers to the lack of an oxygen atom, differentiating it from D-ribose. Specifically:
- Both D-ribose and 2-deoxy-D-ribose share the same basic five-carbon backbone.
- In 2-deoxy-D-ribose, the hydroxyl group attached to the second carbon is replaced by a hydrogen atom. This is the key structural difference.
- As with D-ribose, 2-deoxy-D-ribose still features an aldehyde group on the first carbon.
Pentose sugars
Pentose sugars, like D-ribose and 2-deoxy-D-ribose, are characterized by having five carbon atoms. These sugars are crucial because they serve as building blocks for larger molecules like RNA and DNA.
- In their linear form, pentoses have a straight chain of five carbon atoms.
- Their molecular formula is typically written as \(\mathrm{C}_5\mathrm{H}_{10}\mathrm{O}_5\), though variations like 2-deoxy-D-ribose show modifications.
- Pentoses can form ring structures, which are crucial for their biological roles.
Hydroxyl groups
Hydroxyl groups (\(-\mathrm{OH}\)) are important chemical groups found in many organic molecules, including sugars. These groups consist of an oxygen atom bonded to a hydrogen atom, and they are critical for the structure and reactivity of sugars like D-ribose.
- Hydroxyl groups increase the solubility of sugars in water, making them capable of participating in metabolic processes.
- They determine the chemical characteristics of the sugars and enable the formation of glycosidic linkages in polysaccharides.
- In D-ribose, hydroxyl groups provide sites for interaction with other molecules, facilitating the function of RNA.
Aldehyde functional group
The aldehyde functional group is a signature feature of aldose sugars like D-ribose. This group consists of a carbon atom double-bonded to an oxygen atom and single-bonded to a hydrogen atom (\(-\mathrm{CH}=\mathrm{O}\)).
- In D-ribose, the aldehyde group is found on the first carbon atom, defining it as an aldopentose.
- This group is reactive and influences the sugar's ability to form various structures, including rings.
- The presence of an aldehyde group makes sugars more accessible for particular pathways in metabolism, playing pivotal roles in energy production and cellular respiration.
