Carbohydrate Chemistry and Classification

Carbohydrate Chemistry and Classification

Carbohydrate Chemistry and Classification

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Monosaccharides: Structure & Isomerism - Sweet Singles

  • Simplest sugars, general formula $(CH_2O)_n$, where $n \ge 3$. Classified by:
    • Carbon count (e.g., Triose, Pentose, Hexose).
    • Functional group (Aldose: aldehyde; Ketose: ketone).
  • Structure:
    • Linear form: Fischer projection.
    • Cyclic form: Haworth projection (Pyranose: 6-membered ring; Furanose: 5-membered ring).
    • Anomeric Carbon: Carbonyl carbon (C1 in aldoses, C2 in ketoses) that becomes chiral upon cyclization.
  • Isomerism:
    • Enantiomers: Non-superimposable mirror images (D- and L-forms). 📌 Most human sugars are D-isomers.
    • Diastereomers: Stereoisomers that are not mirror images.
      • Epimers: Differ in configuration at ONE specific chiral carbon (e.g., Glucose/Galactose at C4).
      • Anomers: Differ in configuration at the anomeric carbon ($\alpha$ and $\beta$ forms); arise from cyclization.

⭐ Glucose and galactose are C4 epimers, while glucose and mannose are C2 epimers. Anomers ($\alpha$ and $\beta$) differ at the anomeric carbon formed during cyclization.

![Glucose Projections](glucose projections)

![Flowchart Diagram](flowchart diagram)

Disaccharides & Oligosaccharides - Double Sugars

  • Disaccharides: Two monosaccharides joined by a glycosidic bond.
    • Sucrose: Glucose + Fructose ($\alpha-1,\beta-2$ linkage). Non-reducing.
    • Lactose: Galactose + Glucose ($\beta-1,4$ linkage). Reducing. Milk sugar.
    • Maltose: Glucose + Glucose ($\alpha-1,4$ linkage). Reducing. Malt sugar.
    • 📌 Reducing: Lactose, Maltose (have free anomeric carbon). Non-reducing: Sucrose.
  • Oligosaccharides: 3-10 monosaccharide units (e.g., Raffinose, Stachyose).

⭐ Sucrose (table sugar), composed of glucose and fructose, is a non-reducing sugar because its anomeric carbons (C1 of glucose and C2 of fructose) are involved in the $\alpha-1,\beta-2$ glycosidic bond.

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Polysaccharides: Types & Functions - Complex Chains

Monosaccharide polymers; glycosidic bonds.

  • Homopolysaccharides (Homoglycans): Single monosaccharide type.
    • Storage:
      • Starch (plants): Amylose ($\\\\alpha$-1,4), Amylopectin ($\\\\alpha$-1,4 & $\\\\alpha$-1,6).
      • Glycogen (animals): $\\\\alpha$-1,4 & $\\\\alpha$-1,6 (highly branched).
    • Structural:
      • Cellulose (plants): $\\\\beta$-1,4 glucose. Indigestible.
      • Chitin (fungi, arthropods): $\\\\beta$-1,4 N-acetylglucosamine.
  • Heteropolysaccharides (Heteroglycans): Multiple monosaccharide types/derivatives.
    • Glycosaminoglycans (GAGs): Repeating disaccharides (amino sugar + uronic acid/galactose). E.g., Hyaluronic acid, Heparin.

⭐ Glycogen, the animal storage polysaccharide, has alpha-1,4 glycosidic bonds for linear chains and alpha-1,6 glycosidic bonds at branch points (every 8-12 residues), enabling compact storage and rapid glucose mobilization.

Polysaccharide structures: Cellulose, starch, glycogen

Carbohydrate Reactions & Tests - Sugar Sleuthing

  • Key Reactions:
    • Oxidation: Aldonic, uronic, aldaric acids.
    • Reduction: Alditols (sorbitol). $R-CHO \rightarrow R-CH_2OH$.
    • Osazone Formation: Phenylhydrazine; characteristic crystals.
    • Esterification: Phosphate esters (G6P, ATP).
  • Qualitative Tests:
    • Molisch's: General (conc. $H_2SO_4$, $\alpha$-naphthol $\rightarrow$ purple ring).
    • Benedict's: Reducing sugars (alkaline $CuSO_4$ $\rightarrow$ brick-red $Cu_2O \downarrow$).
    • Barfoed's: Monosaccharides (acidic $Cu(CH_3COO)_2$ $\rightarrow$ faster red $Cu_2O \downarrow$).
    • Seliwanoff's: Ketoses (resorcinol, $HCl$ $\rightarrow$ cherry-red).
    • Bial's: Pentoses (orcinol, $FeCl_3, HCl$ $\rightarrow$ blue-green).
    • Iodine: Starch (blue); Glycogen (red-brown).

⭐ Benedict's test distinguishes reducing sugars, which possess a free aldehyde or ketone group, from non-reducing sugars. The formation of a colored precipitate indicates a positive result.

Benedict’s test for reducing sugars

High‑Yield Points - ⚡ Biggest Takeaways

  • Carbohydrates are polyhydroxy aldehydes or ketones.
  • Key monosaccharides: glucose, fructose, galactose. Key disaccharides: sucrose (non-reducing), lactose, maltose.
  • Epimers (e.g., glucose/galactose at C4) differ at one chiral center.
  • Anomers (α/β) differ at the anomeric carbon.
  • Reducing sugars have a free anomeric carbon; sucrose is non-reducing.
  • Glycogen (animal storage) has α-1,4 and α-1,6 linkages.
  • Cellulose (plant structure) has β-1,4 linkages, indigestible by humans.

Practice Questions: Carbohydrate Chemistry and Classification

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What is the optimal time for alginate impression material gel formation at 20°C?

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Flashcards: Carbohydrate Chemistry and Classification

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The sites of synthesis of glycosaminoglycans (GAG) are _____ and golgi apparatus.

TAP TO REVEAL ANSWER

The sites of synthesis of glycosaminoglycans (GAG) are _____ and golgi apparatus.

endoplasmic reticulum

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