University Biochemistry  |  Exam-Ready Lecture Notes

Carbohydrates

Complete molecular formulas, structural diagrams, biological significance, clinical correlations & industrial applications

Monosaccharides Disaccharides Polysaccharides Isomerism Metabolism Clinical Relevance Industrial Applications

1 Introduction & Definition

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

2 Classification of Carbohydrates

CLASSIFICATION FLOWCHART
CARBOHYDRATES — Cn(H₂O)n
MONOSACCHARIDES
cannot be hydrolysed
Triose (C₃)
Tetrose (C₄)
Pentose (C₅)
Hexose (C₆)
Heptose (C₇)
OLIGOSACCHARIDES
2–10 monosaccharide units
Disaccharides (2)
Trisaccharides (3)
Tetrasaccharides (4)
POLYSACCHARIDES
>10 monosaccharide units
Homopolysaccharides
Heteropolysaccharides
CategoryUnitsFormulaKey ExamplesSolubility
Monosaccharides1CnH2nOnGlucose, Fructose, RiboseSoluble, sweet
Disaccharides2C12H22O11Sucrose, Maltose, LactoseSoluble, sweet
Oligosaccharides3–10VariableRaffinose, StachyosePartially soluble
Polysaccharides>10(C6H10O5)nStarch, Glycogen, CelluloseInsoluble/colloidal

3 Monosaccharides – Formulas & Structures

3.1 Molecular Formulas

SugarTypeMolecular FormulaCarbon #Functional Group
GlyceraldehydeTriose, AldoseC₃H₆O₃3–CHO
DihydroxyacetoneTriose, KetoseC₃H₆O₃3C=O
ErythroseTetrose, AldoseC₄H₈O₄4–CHO
RibosePentose, AldoseC₅H₁₀O₅5–CHO
DeoxyribosePentose, AldoseC₅H₁₀O₄5–CHO
GlucoseHexose, AldoseC₆H₁₂O₆6–CHO at C1
FructoseHexose, KetoseC₆H₁₂O₆6C=O at C2
GalactoseHexose, AldoseC₆H₁₂O₆6–CHO at C1
MannoseHexose, AldoseC₆H₁₂O₆6–CHO at C1
SedoheptuloseHeptose, KetoseC₇H₁₄O₇7C=O

3.2 Structural Representations

D-Glucose — Open Chain (Fischer Projection)

Fischer Projection — D-Glucose (C₆H₁₂O₆)
CHO ← C1 — Aldehyde group (reducing end) | H ———C———OH ← C2 — OH on RIGHT (D-configuration) | HO ———C———H ← C3 | H ———C———OH ← C4 | H ———C———OH ← C5 — reference carbon (determines D or L) | 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 | | 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)

D-Fructose — Furanose Ring (Haworth)

β-D-Fructofuranose (5-membered ring)
HOCH₂ O CH₂OH \ | / C5 ——C4—C3 | \ OH C2 | OH (β: above ring) | C1H₂OH

D-Ribose — Open Chain

Fischer Projection — D-Ribose (C₅H₁₀O₅)
CHO ← C1 | H ———C———OH ← C2 | H ———C———OH ← C3 | H ———C———OH ← C4 | CH₂OH ← C5

3.3 Classification by Carbon Number

Carbon #NameAldose ExamplesKetose ExamplesBiological Role
3TrioseGlyceraldehydeDihydroxyacetoneGlycolysis intermediates
4TetroseErythrose, ThreoseErythulosePentose phosphate pathway
5PentoseRibose, Arabinose, XyloseRibulose, XyluloseRNA/DNA backbone, ATP, NADH
6HexoseGlucose, Galactose, MannoseFructosePrimary energy source, glycogen, starch
7HeptoseSedoheptuloseCalvin 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)
Structural Isomers
Different functional groups
or connectivity
e.g. Glucose vs. Fructose
Stereoisomers
Enantiomers
Mirror images
D-glucose / L-glucose
Diastereomers
Non-mirror; differ
at ≥1 chiral center
Glucose / Galactose
Anomers
Differ at C1 only
α-glucose / β-glucose
Epimers
Differ at one
specific C only
Glucose / Galactose (C4)

4.1 Structural Isomers

Structural Isomers: Glucose vs Fructose (Both C₆H₁₂O₆)
GLUCOSE (Aldohexose) FRUCTOSE (Ketohexose) ════════════════════ ═════════════════════ C1: CHO ← aldehyde C1: CH₂OH C2: H–C–OH C2: C=O ← ketone C3: HO–C–H C3: HO–C–H C4: H–C–OH C4: H–C–OH C5: H–C–OH C5: H–C–OH C6: CH₂OH C6: CH₂OH

4.2 Enantiomers: D- and L-Sugars

D-Glucose vs L-Glucose (Mirror Images)
D-Glucose L-Glucose ════════════ ════════════ CHO CHO | | H ——C—— OH HO ——C—— H | | HO ——C—— H H ——C—— OH | | H ——C—— OH HO ——C—— H | | H ——C—— OH ← C5 (ref) HO ——C—— H ← C5 (ref) | | 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.
Propertyα-D-Glucoseβ-D-Glucose
OH at C1Below ring (axial)Above ring (equatorial)
Specific rotation+112.2°+18.7°
Equilibrium in water~36%~64%
StabilityLess stableMore stable (equatorial OH)
SignificanceForms glycogen, starch (α-1,4)Forms cellulose (β-1,4)

4.4 Optical Activity

5 Disaccharides

Two monosaccharide units linked by a glycosidic bond (formed via condensation — loss of H₂O). General formula: C₁₂H₂₂O₁₁.

5.1 Glycosidic Bond Formation

Condensation Reaction Monosaccharide₁–OH + HO–Monosaccharide₂ → Monosaccharide₁–O–Monosaccharide₂ + H₂O

5.2 Maltose (Malt Sugar)

PropertyDetails
Molecular formulaC₁₂H₂₂O₁₁
CompositionGlucose + Glucose
Glycosidic bondα-1,4 (C1 of glucose₁ → C4 of glucose₂)
Reducing sugar?Yes (free anomeric C1 on second glucose)
Enzyme for hydrolysisMaltase (α-glucosidase)
Natural sourceGerminating barley, starch hydrolysis

Chemical Equations — Maltose

Enzymatic Hydrolysis C₁₂H₂₂O₁₁ + H₂O →(Maltase)→ 2 C₆H₁₂O₆ (Glucose)
Fermentation to Ethanol C₁₂H₂₂O₁₁ + H₂O →(Yeast)→ 4 C₂H₅OH + 4 CO₂
Combustion C₁₂H₂₂O₁₁ + 12 O₂ → 12 CO₂ + 11 H₂O + ΔH

5.3 Lactose (Milk Sugar)

PropertyDetails
Molecular formulaC₁₂H₂₂O₁₁
CompositionGalactose + Glucose
Glycosidic bondβ-1,4 (C1 galactose → C4 glucose)
Reducing sugar?Yes
EnzymeLactase (β-galactosidase)
Sweetness~16% as sweet as sucrose
Hydrolysis of Lactose C₁₂H₂₂O₁₁ + H₂O →(Lactase)→ C₆H₁₂O₆ (Galactose) + C₆H₁₂O₆ (Glucose)
Hydrogenation Lactose + H₂ →(Ni catalyst)→ Lactitol (sugar alcohol — used in sugar-free products)

5.4 Sucrose (Table Sugar)

PropertyDetails
Molecular formulaC₁₂H₂₂O₁₁
Compositionα-Glucose + β-Fructose
Glycosidic bondα-1,β-2 (C1 glucose → C2 fructose; both anomeric carbons linked)
Reducing sugar?No — both anomeric carbons are involved in the bond
EnzymeSucrase (invertase)
Optical rotation+66.5° (dextrorotatory)
Hydrolysis (Inversion) C₁₂H₂₂O₁₁ + H₂O →(Sucrase/acid)→ C₆H₁₂O₆ (Glucose, +52.7°) + C₆H₁₂O₆ (Fructose, –92°) Net rotation changes from +66.5° to ~–20° → called INVERT SUGAR
Complete Combustion C₁₂H₂₂O₁₁ + 12 O₂ → 12 CO₂ + 11 H₂O ΔG = –5644 kJ/mol
Dehydration (concentrated H₂SO₄) C₁₂H₂₂O₁₁ →(conc. H₂SO₄)→ 12 C + 11 H₂O (charring/blackening)

5.5 Reducing vs. Non-Reducing Sugars

Reducing Sugars

  • Free anomeric –OH (C1 in aldoses)
  • Reduce Benedict's, Fehling's, Tollens' reagents
  • Examples: Glucose, Fructose, Maltose, Lactose, Galactose
  • Undergo mutarotation in solution

Non-Reducing Sugars

  • Both anomeric carbons engaged in glycosidic bond
  • Cannot reduce oxidizing reagents
  • Examples: Sucrose, Trehalose
  • Do not show mutarotation

5.6 Isomaltose

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

PropertyAmyloseAmylopectin
% in starch~20–30%~70–80%
StructureUnbranched, helicalBranched
Bond typeα-1,4 onlyα-1,4 (chain) + α-1,6 (branch)
Branch frequencyNoneEvery 24–30 glucose units
Iodine testDeep blue-blackPurple-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")

6.3 Cellulose

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

6.5 Summary Table — Polysaccharides

PolysaccharideMonomerBond TypeFunctionLocation
Starch (amylose)α-D-Glucoseα-1,4Energy storagePlants
Starch (amylopectin)α-D-Glucoseα-1,4 + α-1,6Energy storagePlants
Glycogenα-D-Glucoseα-1,4 + α-1,6Energy storageAnimals (liver, muscle)
Celluloseβ-D-Glucoseβ-1,4StructuralPlant cell walls
ChitinN-Acetylglucosamineβ-1,4StructuralFungi, arthropods
Hyaluronic acidGlcUA + GlcNAcβ-1,4 / β-1,3Connective tissue, lubricationSynovial 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.

Amino SugarParent SugarFormulaBiological Role
D-GlucosamineGlucoseC₆H₁₃NO₅Component of chitin, glycoproteins, cartilage
N-Acetylglucosamine (GlcNAc)GlucoseC₈H₁₅NO₆Chitin, peptidoglycan (bacterial wall), glycoproteins
D-GalactosamineGalactoseC₆H₁₃NO₅Cartilage (chondroitin sulfate), blood group antigens
D-MannosamineMannoseC₆H₁₃NO₅Glycoproteins, cell recognition
Muramic acidGlcNAcC₉H₁₇NO₇Peptidoglycan of bacterial cell walls
Neuraminic acid (sialic acid)MannosamineC₁₁H₁₉NO₉Cell 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 | H ———C———NH₂ ← C2: –OH replaced by –NH₂ | HO ———C———H | H ———C———OH | H ———C———OH | CH₂OH

8 Vitamin C as a Carbohydrate Derivative

Reversible Oxidation (Antioxidant Action) L-Ascorbic Acid (C₆H₈O₆) ⇌ Dehydroascorbic Acid (C₆H₆O₆) + 2H⁺ + 2e⁻

Biological Functions

⚠️ Deficiency — Scurvy
Without vitamin C, collagen synthesis fails → scurvy: bleeding gums, perifollicular hemorrhages, poor wound healing, corkscrew hairs, arthralgia, anemia. Daily requirement: 65–90 mg/day (adults); UL = 2000 mg/day.

9 Biological Importance & Metabolism

9.1 Glycolysis (Cytoplasm)

Breakdown of one glucose → 2 pyruvate. Occurs in all cells. Does NOT require oxygen.

Net Equation of Glycolysis C₆H₁₂O₆ + 2 ADP + 2 Pᵢ + 2 NAD⁺ → 2 C₃H₄O₃ (Pyruvate) + 2 ATP + 2 NADH + 2 H₂O

Net ATP yield from glycolysis alone: 2 ATP

9.2 Krebs Cycle (Mitochondrial Matrix)

Pyruvate (×2) → Acetyl-CoA → enters the TCA cycle.

Overall Equation per Glucose (TCA cycle ×2) 2 Acetyl-CoA + 6 H₂O + 2 ADP + 2 Pᵢ → 4 CO₂ + 2 ATP + 6 NADH + 2 FADH₂

9.3 Oxidative Phosphorylation & Total ATP Yield

StageNADH producedFADH₂ producedATP (direct)Approx. ATP total
Glycolysis202~7
Pyruvate → Acetyl-CoA200~5
Krebs Cycle (×2)622~22
Total per Glucose1024~30–32 ATP
Complete Aerobic Oxidation of Glucose C₆H₁₂O₆ + 6 O₂ → 6 CO₂ + 6 H₂O + ~30–32 ATP ΔG° = –2870 kJ/mol

9.4 Structural Roles

9.5 Immunological & Cell Signaling Roles

9.6 Brain & Nervous System

🧠 Key Fact
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

10 Clinical Relevance

Diabetes Mellitus

  • Type 1: Autoimmune destruction of β-cells → no insulin → hyperglycemia
  • Type 2: Insulin resistance → relative insulin deficiency
  • Hyperglycemia → glycation of proteins (HbA1c used for diagnosis/monitoring)
  • Management: insulin, metformin, dietary carbohydrate restriction

Lactose Intolerance

  • Deficiency of intestinal lactase
  • Undigested lactose fermented by colonic bacteria → bloating, diarrhea, cramps
  • Management: lactase supplements, lactose-free dairy, fermented products (yogurt)

Glycogen Storage Diseases (GSDs)

  • Enzyme deficiencies in glycogen synthesis/breakdown
  • Type I (von Gierke): glucose-6-phosphatase deficiency → hypoglycemia, hepatomegaly
  • Type II (Pompe): lysosomal acid α-glucosidase deficiency → muscle weakness
  • Type V (McArdle): muscle phosphorylase deficiency → exercise intolerance

Scurvy

  • Vitamin C deficiency → impaired collagen hydroxylation
  • Symptoms: bleeding gums, petechiae, poor wound healing, perifollicular hemorrhage
  • Treatment: vitamin C supplementation (200–500 mg/day)
ConditionCarbohydrate DefectKey SymptomTreatment
Diabetes MellitusImpaired glucose uptake/regulationHyperglycemia, polyuria, polydipsiaInsulin, oral hypoglycemics
Lactose IntoleranceLactase deficiencyBloating, diarrhea after dairyLactase enzyme, avoidance
GalactosemiaGalactose-1-phosphate uridyltransferase deficiencyLiver failure, cataracts, intellectual disabilityGalactose-free diet
FructosuriaFructokinase deficiencyBenign — fructose in urineNo treatment needed
Von Gierke DiseaseGlucose-6-phosphatase deficiencySevere hypoglycemia, hepatomegalyFrequent cornstarch feeds
ScurvyVitamin C (ascorbic acid) deficiencyBleeding gums, poor healingVitamin C supplementation

11 Sources of Carbohydrates

CategorySpecific SourcesPrimary CarbohydrateNotes
Cereal GrainsWheat, rice, maize, oats, barleyStarch (amylose + amylopectin)Staple energy source globally
Root VegetablesPotato, sweet potato, yam, cassavaStarchHigh glycemic index when cooked
LegumesLentils, peas, beans, chickpeasStarch + oligosaccharides (raffinose)Also high in fiber and protein
FruitsBanana, mango, grapes, datesFructose, glucose, sucroseSimple sugars — rapid energy
DairyMilk, yogurt, cheeseLactoseYogurt has reduced lactose (fermented)
Refined SugarsTable sugar, honey, HFCS, syrupsSucrose, glucose, fructoseEmpty calories — minimal nutrients
Industrial FermentationCorn starch hydrolysis, sugarcaneGlucose, ethanolUsed in biofuels, pharmaceuticals
BiotechnologyMicrobial production (recombinant)Cyclodextrins, xanthan gumFood additives, drug delivery

12 Industrial & Medical Applications

12.1 Food Industry

12.2 Pharmaceutical Industry

12.3 Biotechnology

12.4 Nutrition & Dietary Supplements

13 Summary Tables & Revision Tools

Master Comparison Table

CompoundFormulaTypeBondReducing?EnzymeFunction
GlucoseC₆H₁₂O₆MonosaccharideYesHexokinaseEnergy, glycolysis
FructoseC₆H₁₂O₆MonosaccharideYesFructokinaseEnergy, invert sugar
GalactoseC₆H₁₂O₆MonosaccharideYesGalactokinaseLactose component, brain galactolipids
RiboseC₅H₁₀O₅MonosaccharideYesRNA backbone, ATP, NADH
MaltoseC₁₂H₂₂O₁₁Disaccharideα-1,4YesMaltaseBeer, baking
LactoseC₁₂H₂₂O₁₁Disaccharideβ-1,4YesLactaseDairy, infant formula
SucroseC₁₂H₂₂O₁₁Disaccharideα-1,β-2NoSucraseTable sugar, sweetener
Starch(C₆H₁₀O₅)nPolysaccharideα-1,4 / α-1,6NoAmylasePlant energy store
Glycogen(C₆H₁₀O₅)nPolysaccharideα-1,4 / α-1,6NoGlycogen phosphorylaseAnimal energy store
Cellulose(C₆H₁₀O₅)nPolysaccharideβ-1,4NoCellulase (absent in humans)Plant cell wall, fiber
Chitin[C₈H₁₃O₅N]nPolysaccharideβ-1,4NoChitinaseExoskeleton, fungal wall

Quick Revision: Key Chemical Equations

1. Aerobic Respiration (Complete) C₆H₁₂O₆ + 6O₂ → 6CO₂ + 6H₂O + 30–32 ATP 2. Anaerobic Fermentation (Yeast) C₆H₁₂O₆ → 2 C₂H₅OH + 2 CO₂ (ΔG = –218 kJ/mol) 3. Sucrose Hydrolysis (Inversion) C₁₂H₂₂O₁₁ + H₂O →(sucrase/H⁺)→ C₆H₁₂O₆ + C₆H₁₂O₆ (glucose) (fructose) 4. Starch Hydrolysis (C₆H₁₀O₅)n + nH₂O →(amylase)→ nC₆H₁₂O₆ 5. Maltose Hydrolysis C₁₂H₂₂O₁₁ + H₂O →(maltase)→ 2 C₆H₁₂O₆ 6. Lactose Hydrolysis C₁₂H₂₂O₁₁ + H₂O →(lactase)→ C₆H₁₂O₆ + C₆H₁₂O₆ (glucose) (galactose) 7. Vitamin C Oxidation C₆H₈O₆ ⇌ C₆H₆O₆ + 2H⁺ + 2e⁻ (Ascorbate → Dehydroascorbate)

Memory Mnemonics

💡 Mnemonics for Exam
  • "All Good Men Love Fructose" → Aldoses: Glyceraldehyde, Mannose, Lactaldehyde, Fructose (structural isomer)
  • "SUcrose = Sugar, Unreduced" → Sucrose is a NON-reducing disaccharide
  • "β = Better for structure" → β-1,4 bonds in cellulose/chitin → structural rigidity
  • "α = Available for energy" → α-1,4 bonds in starch/glycogen → readily digestible energy stores
  • D sugars = OH at reference carbon on the RIGHT in Fischer projection
  • GLAD: Glycogen (Liver & muscle), Amylopectin (Dense branching), → both α-1,6 branches

Exam-Focused Quick-Fire Facts

QuestionAnswer
Most common monosaccharide in biology?D-Glucose
Only non-reducing disaccharide listed?Sucrose
Bond in cellulose vs starch?β-1,4 (cellulose) vs α-1,4 (starch)
Energy yield per glucose (aerobic)?~30–32 ATP
Vitamin C deficiency disease?Scurvy
Milk sugar?Lactose (Glucose + Galactose)
Animal storage polysaccharide?Glycogen (liver & muscle)
Most abundant organic polymer on Earth?Cellulose
Amino sugar in chitin?N-Acetylglucosamine (GlcNAc)
Pentos found in RNA?Ribose (C₅H₁₀O₅)
Enzyme that breaks starch?Amylase (salivary & pancreatic)
What is mutarotation?Interconversion of α and β anomers in solution until equilibrium
Glycemic index of pure glucose?100 (reference standard)
What is invert sugar?Equimolar mix of glucose + fructose from sucrose hydrolysis
Heparin chemical class?Glycosaminoglycan (anticoagulant)