Biochemistry · Topic
Carbohydrate chemistry !
Sugars differ by their carbonyl group, their number of carbons and the direction of their OH groups; glycosidic bonds join them together.
Updated 2026-11-01
Key facts
- Aldoses (aldehyde group: glucose, galactose) and ketoses (ketone group: fructose); named by carbon count: trioses, pentoses, hexoses.
- D or L series depends on the OH of the chiral carbon farthest from the carbonyl; nearly all body sugars are D.
- Epimers differ at one chiral carbon only. Glucose and galactose are C4 epimers; glucose and mannose are C2 epimers.
- Ring closure turns the carbonyl carbon into the anomeric carbon: α (OH down in the Haworth projection) or β (up). Mutarotation interconverts them in solution.
- A glycosidic bond is α or β according to the anomer that forms it: starch and glycogen use α-1,4 and α-1,6; cellulose uses β-1,4, which humans cannot digest.
In detail
- 1. A monosaccharide is a polyhydroxy aldehyde or ketone; glyceraldehyde (an aldotriose) is the reference for the D/L series.
- 2. Isomers share a formula (glucose, fructose and galactose are all C₆H₁₂O₆) but differ in structure. Stereoisomers change only the spatial direction of the OH groups.
- 3. Hexoses cyclise: the C5 OH attacks the carbonyl and forms a hemiacetal (pyranose, six-membered ring) or a hemiketal (furanose, the five-membered ring of fructose).
- 4. The new OH on the anomeric carbon can point α or β; in water glucose sits in equilibrium, mostly β.
- 5. A reducing sugar keeps its anomeric carbon free and can open its ring (glucose, lactose, maltose). Sucrose joins both anomeric carbons (α1→β2) and is non-reducing.
- 6. Exam disaccharides: maltose (glucose-α1,4-glucose), lactose (galactose-β1,4-glucose) and sucrose (glucose-α1,β2-fructose). Each has its own brush-border disaccharidase.
- 7. Derivatives: amino sugars (glucosamine, N-acetylgalactosamine), uronic acids (glucuronic, iduronic), deoxy sugars (deoxyribose) and sugar alcohols (sorbitol). They build glycosaminoglycans and glycoproteins.
Memory aid
"GAlactose = Glucose with carbon 4 Altered": a C4 epimer.
- Also called
- Isomers, anomers and glycosidic bonds
Clinical notes
- Lactose intolerance reflects loss of lactase, which cleaves the β1,4 bond of lactose; undigested sugar is fermented in the colon.
- Cellulose (fibre) passes through the gut undigested because no human enzyme cleaves the β1,4 bond between glucoses.
- Urine reducing-substance tests pick up galactose or fructose, useful when the glucose dipstick is negative.
Pathways
Related conditions
Related
- Glucose
- Fructose
- Galactose
- Glycogen
- Hyaluronic acid (hyaluronan)
- Glycosaminoglycans (mucopolysaccharides)
Test yourself
Think of the answer, then tap the question to see it.
How are glucose and galactose related chemically?
They are C4 epimers: they differ only in the direction of the OH on that carbon.
Why is sucrose not a reducing sugar?
Its bond joins the anomeric carbons of glucose and fructose, so neither is free to open the ring and act as a reducing agent.
What distinguishes an α anomer from a β anomer?
The position of the anomeric OH after ring closure: down (α) or up (β) in the Haworth projection.
Why can humans digest starch but not cellulose?
Starch has α-1,4 bonds that amylase cleaves; cellulose has β-1,4 bonds and we have no enzyme to hydrolyse them.
Educational information, not medical advice. For any symptom, see a health professional.
Sources: Metabolism of carbohydrates and carbohydrate derivatives (Reactome, 2026); Digestion of dietary carbohydrate (Reactome, 2026); beta-Lactose (CID 6134) (PubChem, NCBI, 2026) · Public domain; Sucrose (CID 5988) (PubChem, NCBI, 2026) · Public domain; Textbook of Biochemistry for Medical Students, 6th ed. (Jaypee Brothers Medical Publishers (Vasudevan DM, Sreekumari S, Vaidyanathan K), 2011).
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Representative model, for educational purposes only.