Carbohydrates (saccharides) are the most abundant organic biomolecules on Earth, defined by the empirical formula (CH₂O)n, reflecting an equal ratio of carbon to water molecules. The term "carbohydrate" literally means hydrates of carbon.
📌 General Formula
Cn(H₂O)n — where n ranges from 3 (trioses) to millions (cellulose). More precisely, monosaccharides follow CnH2nOn.
Key Characteristics
Composed of C, H, and O (ratio H:O = 2:1)
Most are sweet-tasting, water-soluble, crystalline solids (simple forms)
Serve as the primary energy currency of all living cells
Play crucial structural, signaling, and immunological roles
Also called glycans when referring to polysaccharide chains
2 Classification of Carbohydrates
CLASSIFICATION FLOWCHART
CARBOHYDRATES — Cn(H₂O)n
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MONOSACCHARIDES cannot be hydrolysed
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Triose (C₃)
Tetrose (C₄)
Pentose (C₅)
Hexose (C₆)
Heptose (C₇)
OLIGOSACCHARIDES 2–10 monosaccharide units
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Disaccharides (2)
Trisaccharides (3)
Tetrasaccharides (4)
POLYSACCHARIDES >10 monosaccharide units
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Homopolysaccharides
Heteropolysaccharides
Category
Units
Formula
Key Examples
Solubility
Monosaccharides
1
CnH2nOn
Glucose, Fructose, Ribose
Soluble, sweet
Disaccharides
2
C12H22O11
Sucrose, Maltose, Lactose
Soluble, sweet
Oligosaccharides
3–10
Variable
Raffinose, Stachyose
Partially soluble
Polysaccharides
>10
(C6H10O5)n
Starch, Glycogen, Cellulose
Insoluble/colloidal
3 Monosaccharides – Formulas & Structures
3.1 Molecular Formulas
Sugar
Type
Molecular Formula
Carbon #
Functional Group
Glyceraldehyde
Triose, Aldose
C₃H₆O₃
3
–CHO
Dihydroxyacetone
Triose, Ketose
C₃H₆O₃
3
C=O
Erythrose
Tetrose, Aldose
C₄H₈O₄
4
–CHO
Ribose
Pentose, Aldose
C₅H₁₀O₅
5
–CHO
Deoxyribose
Pentose, Aldose
C₅H₁₀O₄
5
–CHO
Glucose
Hexose, Aldose
C₆H₁₂O₆
6
–CHO at C1
Fructose
Hexose, Ketose
C₆H₁₂O₆
6
C=O at C2
Galactose
Hexose, Aldose
C₆H₁₂O₆
6
–CHO at C1
Mannose
Hexose, Aldose
C₆H₁₂O₆
6
–CHO at C1
Sedoheptulose
Heptose, Ketose
C₇H₁₄O₇
7
C=O
3.2 Structural Representations
D-Glucose — Open Chain (Fischer Projection)
Fischer Projection — D-Glucose (C₆H₁₂O₆)
CHO ← C1 — Aldehyde group (reducing end)
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H ———C———OH ← C2 — OH on RIGHT (D-configuration)
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HO ———C———H ← C3
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H ———C———OH ← C4
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H ———C———OH ← C5 — reference carbon (determines D or L)
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CH₂OH ← C6 — primary alcohol
D-Glucose — Haworth Projection (Pyranose Ring)
Haworth Projection — α-D-Glucopyranose
CH₂OH
|
6 |
O C5
/ \
C1–OH H C4–OH
(α: OH | |
below) C3 H
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OH OH
\ /
C2
|
OH
α-anomer: OH at C1 is BELOW the ring (trans to –CH₂OH)
β-anomer: OH at C1 is ABOVE the ring (cis to –CH₂OH)
CHO ← C1
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H ———C———OH ← C2
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H ———C———OH ← C3
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H ———C———OH ← C4
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CH₂OH ← C5
3.3 Classification by Carbon Number
Carbon #
Name
Aldose Examples
Ketose Examples
Biological Role
3
Triose
Glyceraldehyde
Dihydroxyacetone
Glycolysis intermediates
4
Tetrose
Erythrose, Threose
Erythulose
Pentose phosphate pathway
5
Pentose
Ribose, Arabinose, Xylose
Ribulose, Xylulose
RNA/DNA backbone, ATP, NADH
6
Hexose
Glucose, Galactose, Mannose
Fructose
Primary energy source, glycogen, starch
7
Heptose
—
Sedoheptulose
Calvin cycle, pentose phosphate pathway
3.4 Aldoses vs. Ketoses
Aldoses
Aldehyde (–CHO) at C1
Reducing sugars (free aldehyde)
Examples: Glucose, Galactose, Mannose, Ribose
Undergo mutarotation
React with Fehling's / Benedict's reagents
Ketoses
Ketone (C=O) at C2
Weaker reducing properties
Examples: Fructose, Ribulose, Xylulose
Also undergo mutarotation in ring form
Form furanose (5-membered) rings preferentially
4 Isomerism
Isomers share identical molecular formulas but differ in structural arrangement or spatial orientation. Carbohydrate isomerism is fundamental to understanding biochemical specificity.
TYPES OF ISOMERISM IN CARBOHYDRATES
ISOMERS (same molecular formula)
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Structural Isomers
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Different functional groups or connectivity e.g. Glucose vs. Fructose
Stereoisomers
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Enantiomers
Mirror images D-glucose / L-glucose
Diastereomers
Non-mirror; differ at ≥1 chiral center Glucose / Galactose
Anomers
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Differ at C1 only α-glucose / β-glucose
Epimers
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Differ at one specific C only Glucose / Galactose (C4)
4.1 Structural Isomers
Structural Isomers: Glucose vs Fructose (Both C₆H₁₂O₆)
D-Glucose L-Glucose
════════════ ════════════
CHO CHO
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H ——C—— OH HO ——C—— H
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HO ——C—— H H ——C—— OH
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H ——C—— OH HO ——C—— H
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H ——C—— OH ← C5 (ref) HO ——C—— H ← C5 (ref)
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CH₂OH CH₂OH
OH on C5 = RIGHT (D) OH on C5 = LEFT (L)
Naturally occurring ✓ Not naturally occurring ✗
Dextrorotatory (+112.2°) Levorotatory
4.3 Anomers (α and β)
📖 Anomers Explained
When the open-chain form cyclises, a new chiral centre forms at C1 (the anomeric carbon). The two forms are called α-anomer (OH at C1 is axial / below the ring) and β-anomer (OH at C1 is equatorial / above the ring). This interconversion in solution is called mutarotation.
Property
α-D-Glucose
β-D-Glucose
OH at C1
Below ring (axial)
Above ring (equatorial)
Specific rotation
+112.2°
+18.7°
Equilibrium in water
~36%
~64%
Stability
Less stable
More stable (equatorial OH)
Significance
Forms glycogen, starch (α-1,4)
Forms cellulose (β-1,4)
4.4 Optical Activity
Dextrorotatory (+): Rotates plane-polarized light to the right. Example: D-glucose (+52.7° at equilibrium)
Levorotatory (–): Rotates light to the left. Example: Fructose (–92°)
Racemic mixture: Equal amounts of (+) and (–) forms — optically inactive (net rotation = 0)
Invert sugar: Equimolar mixture of glucose and fructose produced by hydrolysis of sucrose; net levorotatory
5 Disaccharides
Two monosaccharide units linked by a glycosidic bond (formed via condensation — loss of H₂O). General formula: C₁₂H₂₂O₁₁.
An isomer of maltose with an α-1,6 glycosidic bond (C1 → C6). Also formula C₁₂H₂₂O₁₁. It is a reducing sugar and yields 2 glucose molecules upon hydrolysis. Found at branch points of glycogen/starch, produced by action of isomaltase.
6 Polysaccharides
Polymers of monosaccharide units (>10) joined by glycosidic bonds. General formula: (C₆H₁₀O₅)n for hexose-based polysaccharides.
6.1 Starch
Property
Amylose
Amylopectin
% in starch
~20–30%
~70–80%
Structure
Unbranched, helical
Branched
Bond type
α-1,4 only
α-1,4 (chain) + α-1,6 (branch)
Branch frequency
None
Every 24–30 glucose units
Iodine test
Deep blue-black
Purple-reddish
Molecular mass
~200,000 Da
~200,000,000 Da
Hydrolysis of Starch
(C₆H₁₀O₅)n + n H₂O →(amylase/acid)→ n C₆H₁₂O₆ (Glucose)
6.2 Glycogen ("Animal Starch")
Formula: (C₆H₁₀O₅)n
Bonds: α-1,4 (linear) + α-1,6 (branches every 8–12 units — more branched than amylopectin)
Stored in liver (glucose homeostasis) and skeletal muscle (fuel for contraction)
Rapidly mobilized by glycogen phosphorylase → Glucose-1-phosphate → enters glycolysis
6.3 Cellulose
Formula: (C₆H₁₀O₅)n — n up to 10,000–15,000
Bonds: β-1,4 glycosidic bonds between β-D-glucose units
Alternating glucose units are flipped 180°, enabling extensive hydrogen bonding → rigid, fibrous structure
Most abundant organic polymer on Earth (~50% of plant biomass)
Humans lack cellulase → not digestible → acts as dietary fiber
Cellulose β-1,4 Linkage vs Starch α-1,4 Linkage
STARCH (α-1,4) CELLULOSE (β-1,4)
══════════════ ══════════════════
Glucose → Glucose → Glucose ← Glucose →
(same orientation) (alternating 180° flip)
Forms coiled HELIX Forms flat, linear SHEETS
Digestible by humans Indigestible — dietary fiber
Energy storage Structural (cell walls)
Iodine → deep blue Iodine → no colour change
6.4 Chitin
Formula: [C₈H₁₃O₅N]n
Polymer of N-acetyl-D-glucosamine linked by β-1,4 bonds
Second most abundant polysaccharide on Earth
Found in: fungal cell walls, arthropod exoskeletons, mollusc shells
Medical use: wound dressings (biocompatible, biodegradable)
6.5 Summary Table — Polysaccharides
Polysaccharide
Monomer
Bond Type
Function
Location
Starch (amylose)
α-D-Glucose
α-1,4
Energy storage
Plants
Starch (amylopectin)
α-D-Glucose
α-1,4 + α-1,6
Energy storage
Plants
Glycogen
α-D-Glucose
α-1,4 + α-1,6
Energy storage
Animals (liver, muscle)
Cellulose
β-D-Glucose
β-1,4
Structural
Plant cell walls
Chitin
N-Acetylglucosamine
β-1,4
Structural
Fungi, arthropods
Hyaluronic acid
GlcUA + GlcNAc
β-1,4 / β-1,3
Connective tissue, lubrication
Synovial fluid, cartilage
7 Amino Sugars & Derivatives
Sugars in which a hydroxyl (–OH) group is replaced by an amino (–NH₂) group, often subsequently acetylated to form N-acetyl derivatives.
Cartilage (chondroitin sulfate), blood group antigens
D-Mannosamine
Mannose
C₆H₁₃NO₅
Glycoproteins, cell recognition
Muramic acid
GlcNAc
C₉H₁₇NO₇
Peptidoglycan of bacterial cell walls
Neuraminic acid (sialic acid)
Mannosamine
C₁₁H₁₉NO₉
Cell surface recognition, viral attachment
🔬 Clinical Note
Glucosamine sulfate supplements are widely used for osteoarthritis. It is a precursor to glycosaminoglycans (GAGs) — the main components of cartilage matrix. Clinical evidence suggests moderate benefit in reducing joint pain.
Structure of D-Glucosamine (Open Chain)
D-Glucosamine — Fischer Projection
CHO
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H ———C———NH₂ ← C2: –OH replaced by –NH₂
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HO ———C———H
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H ———C———OH
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H ———C———OH
|
CH₂OH
8 Vitamin C as a Carbohydrate Derivative
Name: L-Ascorbic Acid
Formula: C₆H₈O₆ (a hexuronic acid lactone — derivative of L-gulonolactone)
Considered a monosaccharide derivative (hexose-derived lactone)
Humans lack the enzyme L-gulonolactone oxidase → cannot synthesize it → must obtain from diet
The brain accounts for ~20% of the body's glucose consumption. Neurons rely almost exclusively on glucose for ATP generation (cannot oxidize fatty acids efficiently). During prolonged fasting, the brain adapts to use ketone bodies as an alternative fuel.
9.7 Dietary Fiber
Insoluble fiber (cellulose, hemicellulose): Increases stool bulk, promotes peristalsis, prevents constipation and colorectal cancer