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NCERT Exemplar · Q27

Q.Aldopentoses named ribose and 2-deoxyribose are found in nucleic acids. What is their relative configuration?

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The relative configuration of ribose and 2-deoxyribose is identical at all chiral centres except C-2, where ribose has an OH group and 2-deoxyribose has only an H atom — they share the same D-configuration at C-4 (the reference carbon), so both belong to the D-series.

The question asks about the relative configuration of two aldopentoses: ribose and 2-deoxyribose. This is a classic concept from carbohydrate chemistry in the context of nucleic acids.

Let’s first understand what “relative configuration” means here. In sugars, the configuration is defined by the chiral centre farthest from the carbonyl group — for aldopentoses, that’s carbon-4 (C-4). If the OH on C-4 points to the right in a Fischer projection, the sugar is D; if to the left, it’s L. This is the reference for the entire family.

Now, ribose and 2-deoxyribose differ only at carbon-2: ribose has an OH group at C-2, while 2-deoxyribose has just a hydrogen (hence “deoxy”). All other chiral centres — C-3 and C-4 — are identical in configuration. Both sugars are naturally occurring in the D-form.

Here’s the step-by-step reasoning:

  1. Identify the chiral centres. Both ribose and 2-deoxyribose are aldopentoses: a five-carbon sugar with an aldehyde group at C-1. The chiral carbons are C-2, C-3, and C-4. (C-1 is not chiral because it’s an aldehyde; C-5 is a primary alcohol, not chiral.)

  2. Compare the structures. In ribose, C-2 has an OH group. In 2-deoxyribose, C-2 has only H — that’s the only difference. The configurations at C-3 and C-4 are exactly the same in both sugars.

  3. Determine the reference carbon. For aldoses, the configuration is assigned based on the highest-numbered chiral carbon — here, C-4. In both ribose and 2-deoxyribose found in nucleic acids, the OH at C-4 is on the right in the Fischer projection, making them D-sugars. …

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