Mnemonics and flowchart and diagrams for chemistry of carbohydrates in biochemistry for bds students

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Chemistry of Carbohydrates - BDS Biochemistry Study Guide

Source: Tietz Textbook of Laboratory Medicine, 7th Ed. (Chapter 35)

MASTER MNEMONIC: "ALL KINGS PREFER DEFINITELY HEXOSE"

Aldehyde or ketone + polyhydroxy = Carbohydrate definition Living organisms use D-configuration almost exclusively Linkage between sugars = glycosidic bond (loss of H₂O) Ketose = carbonyl NOT at end (e.g. Fructose) Pyranose = 6-membered ring; Furanose = 5-membered ring Reducing sugars have a free anomeric -OH (glucose, galactose, maltose, lactose) --- Sucrose is NON-reducing D-sugars: -OH on C5 is on the RIGHT in Fischer projection Hexoses are the most biologically important (6 carbons) Equilibrium in solution = mutarotation (α ⇌ β) XEH= Example: glucose 36% α, 64% β at equilibrium

1. CLASSIFICATION FLOWCHART

                        CARBOHYDRATES
                (Polyhydroxy aldehydes/ketones)
                            |
         ___________________↓___________________
        |                   |                   |
  MONOSACCHARIDES     OLIGOSACCHARIDES     POLYSACCHARIDES
  (1 sugar unit)      (2–10 units)         (>10 units)
        |                   |                   |
   By carbonyl:      DISACCHARIDES:         HOMOPOLYSACCHARIDES:
   Aldose (CHO        Maltose (Glc-Glc)      Starch (amylose +
    at C1)            Lactose (Gal-Glc)      amylopectin)
   Ketose (C=O        Sucrose (Glc-Fru)      Glycogen
    at C2)                                   Cellulose
        |
   By carbon #:      HETEROPOLYSACCHARIDES:
   Triose  (C3)       Hyaluronic acid
   Tetrose (C4)       Heparin
   Pentose (C5)       Chondroitin sulfate
   Hexose  (C6)
   Heptose (C7)

Mnemonic for carbon series: "Three Tiny Penguins Have High Hats" Tri - Tetr - Pent - Hex - Hept

2. ALDOSE vs KETOSE - QUICK MNEMONIC

"ALD-end, KET-middle"

ALDose = aldehyde = END of chain (C1)
KETose = ketone = MIDDLE of chain (C2)

Key examples:

Sugar	Type	Carbons
Glucose	Aldohexose	6
Galactose	Aldohexose	6
Mannose	Aldohexose	6
Fructose	Ketohexose	6
Ribose	Aldopentose	5

Mnemonic: "GGMF" = "Good Girls Make Fudge" Glucose (Aldo), Galactose (Aldo), Mannose (Aldo), Fructose (Keto)

3. FISCHER PROJECTION - D vs L SUGARS

Typical six-carbon sugars showing D-Glucose, L-Glucose, D-Fructose, and D-Galactose with Fischer projections

Mnemonic: "DROIT = D = RIGHT"

D-sugars: -OH on the penultimate carbon (C5 in hexose) is on the Right
L-sugars: -OH is on the Left

4. RING STRUCTURES - PYRANOSE vs FURANOSE

Haworth formula showing pyranose and furanose ring structures with glucose and fructose

Mnemonic: "PY-6, FU-5"

Pyranose = 6-membered ring (like pyramid with 6 sides in your mind)
Furanose = 5-membered ring (Funny five)

Alpha vs Beta - Mnemonic: "ALPHA is Below, BETA is aBove" In Haworth formula:

α = -OH at anomeric carbon is below the ring plane
β = -OH at anomeric carbon is above the ring plane

5. MUTAROTATION FLOWCHART

  α-D-Glucose (+113°)
        ↕  (mutarotation in aqueous solution)
  Open-chain aldehyde form (trace amount)
        ↕
  β-D-Glucose (+19.7°)

  EQUILIBRIUM: 36% α ← ——————————————→ 64% β
  Final specific rotation = +52.5°

Mnemonic: "Mutarotation = Mu-ta-ro-ta-tion = Mix Till Rotation Reaches 52.5"

6. α vs β GLUCOSE (Hemiacetal Ring)

Alpha-D-Glucose and Beta-D-Glucose hemiacetal ring structures

7. DISACCHARIDES - "MLS" MNEMONIC

"Mango Lasts Sweet"

Disaccharide	Components	Bond	Reducing?
Maltose	Glucose + Glucose	α(1→4)	YES
Lactose	Galactose + Glucose	β(1→4)	YES
Sucrose	Glucose + Fructose	α(1→2)β	NO

Why is sucrose non-reducing? Both anomeric carbons are involved in the glycosidic bond, leaving no free -OH to reduce Cu²⁺.

Mnemonic: "Sucrose is Special - BOTH ends bonded"

Structural formulas of Maltose, Lactose, and Sucrose with reducing groups indicated

8. REDUCING SUGARS - MNEMONIC

"MALL Reduces - Sucrose Does NOT"

Maltose - reducing
All monosaccharides (glucose, fructose, galactose) - reducing
Lactose - reducing
Lactulose - reducing
Sucrose - NON-reducing (no free anomeric carbon)

Why do reducing sugars reduce? Free aldehyde → enol → enol anion in alkaline solution → reduces Cu²⁺ (cupric) → Cu⁺ (cuprous) This is the basis of Benedict's and Fehling's tests

9. POLYSACCHARIDES COMPARISON TABLE

Feature	Starch (Amylose)	Starch (Amylopectin)	Glycogen	Cellulose
Source	Plants	Plants	Animals/Humans	Plants
Linkage	α(1→4)	α(1→4) + α(1→6)	α(1→4) + α(1→6)	β(1→4)
Branching	None	Every 24-30 C	Every 8-12 C	None
Digestibility	YES	YES	YES	NO

Mnemonic: "SAGC" = "Starch And Glycogen Coil, Cellulose Can't"

Starch/Glycogen: α-linkage = digestible, forms helical coils
Cellulose: β-linkage = NOT digestible (humans lack β-glucosidase)

10. DIGESTION & ABSORPTION FLOWCHART

DIETARY STARCH/GLYCOGEN
        ↓ Salivary amylase (mouth)
  Intermediate dextrins + Maltose
        ↓ (Acid pH of stomach STOPS amylase)
        ↓ Pancreatic amylase (small intestine)
  Oligosaccharides + Maltose
        ↓ Disaccharidases (intestinal mucosa)
     Maltase → Glucose + Glucose
     Lactase → Glucose + Galactose
     Sucrase → Glucose + Fructose
        ↓ Active transport
  Absorbed into portal circulation
        ↓
  LIVER (glucose homeostasis)

Mnemonic: "SaMPLE = Salivary, Mucosa, Pancreas, Liver, Enterocytes"

11. GLYCOPROTEINS - O-LINKED vs N-LINKED

Mnemonic: "O-SiT, N-ASK"

O-linked: to Serine / Threonine (-OH group)
N-linked: to Asparagine (-NH₂ group = Keto group side chain nitrogen)

Functions of carbohydrate chains: regulate protein lifespan, cell-cell recognition, targeting of secreted proteins (antibodies, hormones, coagulation factors).

12. QUICK REVISION: KEY NUMBERS TO REMEMBER

Parameter	Value
α-D-glucose specific rotation	+113°
β-D-glucose specific rotation	+19.7°
Equilibrium mixture rotation	+52.5°
Equilibrium ratio α:β	36% : 64%
Amylopectin branch interval	every 24-30 carbons
Glycogen branch interval	every 8-12 carbons
Reducing power of disaccharide vs 2 monosaccharides	~40%

Mnemonic for rotations: "ALPHa has 113, BETA is boring 19.7, MIX gives 52.5"

13. DENTAL RELEVANCE (BDS-specific)

Sucrose and dental caries - FLOWCHART:

Sucrose (dietary)
    ↓ Streptococcus mutans
    ↓ (uses glucosyltransferase)
Lactic acid + Glucan (sticky plaque matrix)
    ↓
Demineralization of enamel (HAP)
    ↓
DENTAL CARIES

Sucrose is the most cariogenic sugar because it has BOTH glucose AND fructose available for bacterial fermentation, AND the glucan forms the adhesive plaque matrix.
Cellulose (fiber) is NOT cariogenic - no α-glucosidase in mouth.
Xylitol (sugar alcohol) - non-fermentable by S. mutans, used in sugar-free gum.

14. OVERALL MASTER FLOWCHART

CARBOHYDRATES
      |
      ├── MONOSACCHARIDES ──── By C: Triose/Tetrose/Pentose/Hexose/Heptose
      |         |                By carbonyl: ALDOSE (end) / KETOSE (middle)
      |         |                By config: D (OH right) / L (OH left)
      |         |                Ring form: PYRANOSE (6) / FURANOSE (5)
      |         |                Anomers: α (below) / β (above)
      |         |
      ├── DISACCHARIDES ──── Maltose (Glc-Glc, α1→4, REDUCING)
      |                       Lactose (Gal-Glc, β1→4, REDUCING)
      |                       Sucrose (Glc-Fru, α1→2β, NON-REDUCING)
      |
      └── POLYSACCHARIDES ── Starch (α-links, digestible, plant storage)
                              Glycogen (α-links, highly branched, animal)
                              Cellulose (β-links, NOT digestible, structural)
                              Glycosaminoglycans (e.g. hyaluronic acid, heparin)

Sources: Tietz Textbook of Laboratory Medicine, 7th Ed., Chapter 35 (Chemistry of Carbohydrates, pp. 1127-1130)

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