Carbohydrates: classification and monosaccharides6 concepts
| Aldotetrose | OH at C2, C3 | + HNO₃ → tartaric acid | Optically active? |
|---|---|---|---|
| D-erythrose | same side | meso | ✗ |
| D-threose | opposite sides | (2S,3S) or (2R,3R) | ✓ |
- Open chain: glucose has 4 chiral C (C2–C5), so stereoisomers, the aldohexoses (8 D, 8 L); fructose has 3 (C3–C5), so (4 D, 4 L). Ring closure adds the anomeric C.
- Not D = dextro. D/L is configuration, (+)/(−) is measured rotation: D-(−)-fructose. L-glucose is the full mirror image, so flip every OH, not just C5. D-fructose shares C3–C5 with D-glucose.
- Quick method. Aldotetroses (, two chiral C) give tartaric acid with . Both OH on one side (erythrose) gives meso, inactive acid; opposite sides (threose) an active one. The lower OH then sets D or L.
| Reagent | Product (formula from the structure) | Shows |
|---|---|---|
| HI, Δ | n-hexane (C₆H₁₄) | six C in an unbranched chain |
| NH₂OH | oxime, C₆H₁₃NO₆ | a C=O is present |
| HCN | cyanohydrin, C₇H₁₃NO₆ | a C=O is present |
| Br₂ water | gluconic acid, C₆H₁₂O₇ | the C=O is a –CHO (one COOH) |
| HNO₃ | saccharic acid, C₆H₁₀O₈ | CH₂OH end also oxidised (two COOH) |
| (CH₃CO)₂O | pentaacetate, C₁₆H₂₂O₁₁ | 5 OH on different carbons |
- Not for gluconic acid. Mild water oxidises only the ; strong also oxidises the end (saccharic diacid). needs a COOH, so no reaction.
- Quick method. Decode an unknown sugar: acetate count = number of OH; an acid with water = aldose; the HI product = carbon skeleton. A giving isopentane (HI) and an acid ( water) is a branched aldopentose.
- Not 'no aldehyde at all'. A little open chain stays in equilibrium, so glucose still reduces Tollens' and gives an oxime. But no 2,4-DNP, Schiff's or product; the ring-locked pentaacetate gives no oxime.
| Anomer | C1 (from the structure) | [α]D |
|---|---|---|
| α-D-glucopyranose | S | +112° |
| β-D-glucopyranose | R | +19° |
- α crystallises from a concentrated solution at 303 K, β from a hot one at 371 K; β melts higher (423 K vs 419 K). In water either changes to the +52.5° mixture: mutarotation.
- Not anomers for glucose and galactose. They differ at C4 (epimers). Anomers differ only at C1.
- Quick method. Haworth of a D-sugar: above the ring; each Fischer right-hand OH points down. Anomeric OH below the ring (trans to ) = α, above = β.
- Not non-reducing for lack of CHO. Tollens' and Fehling's are basic, and base turns fructose into glucose and mannose via an enediol. So fructose, like every monosaccharide, reduces both.
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15 more concepts in 5 topics
Disaccharides and polysaccharides; Amino acids; Peptides, proteins and enzymes; Vitamins; and Nucleic acids. Read the first part free. Sign in free with Google to read the rest and download the PDF.
Disaccharides and polysaccharides4 concepts
- Glycosidic link and reducing sugars8×
- Sucrose and invert sugar10×
- Maltose and lactose13×
- Starch, cellulose and glycogen9×
Amino acids3 concepts
- α-Amino acids: essential and types10×
- Side chains and one-letter codes13×
- Zwitterion, isoelectric point, chirality6×
Peptides, proteins and enzymes4 concepts
- Peptide bond and peptide counting17×
- Levels of protein structure7×
- Fibrous vs globular; denaturation8×
- Enzymes7×
Vitamins2 concepts
- Fat-soluble vs water-soluble5×
- Vitamin names and deficiency diseases8×
Nucleic acids2 concepts
- Nucleotides, DNA and RNA8×
- Bases and base pairing6×
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