Question:medium

(i) Write a short note on the cyclic structure of glucose.
(ii) What is the difference between a nucleoside and a nucleotide? (2+2=4)

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Glucose: C-5 \( -OH \) closes onto the C-1 \( -CHO \) to give a six-membered pyranose hemiacetal, creating the anomeric carbon and the \( \alpha \)/\( \beta \) anomers. Nucleoside = base + sugar; nucleotide = base + sugar + phosphate.
Updated On: Jul 10, 2026
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Solution and Explanation

Part (i): Ring form of glucose.

Step 1: The clues.
Pure glucose gives two solids with different melting points and optical rotations that slowly settle to a common value in water (mutarotation), and it fails a few typical aldehyde tests. An open \(-CHO\) chain cannot account for this, so a cyclic structure is proposed.

Step 2: Intramolecular hemiacetal.
The oxygen of the C-5 hydroxyl adds across the C-1 carbonyl within the same molecule. An alcohol adding to an aldehyde gives a hemiacetal; here it produces a six-membered oxygen-containing ring named the pyranose form.

Step 3: Birth of two anomers.
Ring closure turns C-1 into a fresh stereocentre, the anomeric carbon. Its \(-OH\) can point down (\(\alpha\)-D-glucopyranose) or up (\(\beta\)-D-glucopyranose). These two diastereomers are the \(\alpha\) and \(\beta\) anomers, differing only at C-1.

Step 4: Take-away.
Because most glucose stays cyclic, the free \(-CHO\) is scarce, which is why some aldehyde reactions do not occur; equilibrium through the open form allows \(\alpha\) and \(\beta\) to interconvert.

Part (ii): Comparing the two units.

Step 5: Two components vs three.
A nucleoside has just two parts, a nitrogen base linked to a pentose sugar at the sugar's C-1' by an N-glycosidic linkage. Examples: adenosine, cytidine.

Step 6: Adding phosphate.
Attach a phosphate group at the C-5' hydroxyl of that sugar and the unit becomes a nucleotide (three parts: base + sugar + phosphate). Examples: adenosine monophosphate (AMP). Chains of nucleotides joined by phosphodiester bonds make up DNA and RNA.
\[ \boxed{\text{nucleotide} = \text{nucleoside} + \text{phosphate}} \]
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