Biomolecules: Carbohydrates, Amino Acids, Nucleic Acids
Apply concepts from Biomolecules: Carbohydrates, Amino Acids, Nucleic Acids to problem-solving. Focus on numerical practice, shortcuts, and real-world applications.
Concept Core
1. Carbohydrates — Classification and Structure
Carbohydrates are polyhydroxy aldehydes or ketones with general formula Cn(H2O)n. Classified as:
Monosaccharides (cannot be hydrolyzed further): Aldoses contain -CHO (glucose, mannose, galactose); ketoses contain C=O (fructose). Carbon count: triose (C3), tetrose (C4), pentose (C5, ribose), hexose (C6, glucose/fructose).
Open-chain D-Glucose (aldohexose with 4 chiral centers):
Glucose (C6H12O6): Open-chain is an aldohexose with 4 chiral centers. In solution, exists predominantly as cyclic hemiacetal — pyranose ring (6-membered). The C1-OH can be axial (-D-glucose) or equatorial (-D-glucose). These are anomers (differ only at the anomeric carbon C1). Mutarotation: fresh solution of either anomer equilibrates to a mixture ( 36%, 64%, trace open-chain) with specific rotation settling at +52.7 degrees.
Fructose (C6H12O6): A ketohexose. Forms a furanose ring (5-membered) via intramolecular hemiketal. Anomeric carbon is C2. Gives positive Tollens' and Fehling's tests despite being a ketone (tautomerizes to glucose/mannose in base via enediol intermediate).
Disaccharides: Sucrose = glucose + fructose (C1- to C2- glycosidic bond, both anomeric carbons locked, NON-reducing).
Maltose = glucose + glucose (C1- to C4, one free anomeric C, reducing).
Lactose = galactose + glucose (C1- to C4, reducing).
Polysaccharides: Starch = amylose (unbranched, -1,4) + amylopectin (branched, -1,4 + -1,6).
Cellulose = -1,4 linked glucose (humans cannot digest — lack -glycosidase).
Glycogen = animal starch (highly branched, -1,4 + -1,6).
2. Amino Acids, Peptides, and Proteins
Amino acids: Alpha-amino acids have NH2 and COOH on the same carbon. All naturally occurring ones are L-configuration (S at -C, except cysteine which is R due to priority change with -CH2SH).
Key amino acid structures:
Glycine (simplest amino acid, achiral)
L-Alanine (simplest chiral amino acid)
Zwitterion: At physiological pH, amino acids exist as H3N+-CHR-COO- (internal salt). Isoelectric point (pI): pH at which net charge = 0. For neutral amino acids: pI = (pKa1 + pKa2)/2. At pH < pI: cation (migrates to cathode). At pH > pI: anion (migrates to anode).
Classification: Acidic (Asp, Glu — extra COOH, low pI ~3), Basic (Lys, Arg, His — extra NH2, high pI ~10), Neutral (Gly, Ala, Val, Leu etc.), Aromatic (Phe, Tyr, Trp). Essential amino acids cannot be synthesized by the body (Val, Leu, Ile, Phe, Trp, Met, Thr, Lys + His, Arg for children).
Peptide bond: Formed by condensation of -COOH of one amino acid with -NH2 of another. Partial double bond character (C-N rotation restricted, planar). Written N-terminus to C-terminus.
Protein structure: Primary (amino acid sequence), Secondary (-helix — H-bonds within same chain, -sheet — H-bonds between chains), Tertiary (3D folding — hydrophobic interactions, disulfide bonds, ionic bonds), Quaternary (multi-subunit assembly, e.g., hemoglobin has 4 subunits).
Enzymes: Biological catalysts (proteins). Highly specific (lock-and-key model). Lower activation energy without being consumed. Named with -ase suffix (urease, lipase). Denatured by heat, pH extremes, heavy metals.
3. Nucleic Acids
Nucleoside = base + sugar (no phosphate). Nucleotide = base + sugar + phosphate.
DNA: Deoxyribose sugar, bases = A, G, C, T (thymine). Double helix with antiparallel strands. Base pairing: A=T (2 H-bonds), G triple-bond C (3 H-bonds). Chargaff's rule: %A = %T, %G = %C.
RNA: Ribose sugar (has 2'-OH), bases = A, G, C, U (uracil replaces thymine). Usually single-stranded. Types: mRNA (messenger), tRNA (transfer, cloverleaf), rRNA (ribosomal).
Key nucleobases:
Adenine (purine base, present in both DNA and RNA)
Uracil (pyrimidine base, replaces thymine in RNA)
4. Vitamins and Hormones
Water-soluble vitamins: B-complex (B1 thiamine, B2 riboflavin, B6 pyridoxine, B12 cobalamin, niacin, folic acid, biotin, pantothenic acid) and C (ascorbic acid). Cannot be stored in body — daily intake needed.
Fat-soluble vitamins: A (retinol — night vision), D (calciferol — calcium absorption), E (tocopherol — antioxidant), K (phylloquinone — blood clotting). Stored in liver/fat tissues.
Hormones: Chemical messengers. Insulin (peptide, lowers blood glucose), adrenaline (amino acid derivative, fight-or-flight), testosterone/estrogen (steroids, sex hormones), thyroxine (iodinated amino acid, metabolism).
The key problem-solving concept is recognizing structural features (reducing vs non-reducing sugars, anomeric carbon, glycosidic linkage type) and applying Chargaff's rules for nucleic acid calculations.
Key Testable Concept
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Comparison Tables
A) Monosaccharide Properties
| Sugar | Type | SMILES (open-chain) | Ring Form | Anomeric C | Key Test Results |
|---|---|---|---|---|---|
| Glucose | Aldohexose | Pyranose (6) | C1 | Tollens +, Fehling +, Osazone yes | |
| Fructose | Ketohexose | Furanose (5) | C2 | Tollens +, Fehling + (enediol), Seliwanoff + fast | |
| Galactose | Aldohexose | Pyranose (6) | C1 | Tollens +, Fehling +, C4 epimer of glucose | |
| Ribose | Aldopentose | Furanose (5) | C1 | RNA sugar, has 2'-OH | |
| Deoxyribose | Aldopentose | Furanose (5) | C1 | DNA sugar, lacks 2'-OH |
B) Disaccharide Comparison
| Disaccharide | Components | Glycosidic Bond | Reducing? | Key Fact |
|---|---|---|---|---|
| Sucrose | Glucose + Fructose | -1,2 | No | Both anomeric C locked; invert sugar on hydrolysis |
| Maltose | Glucose + Glucose | -1,4 | Yes | From starch hydrolysis; free C1 on second glucose |
| Lactose | Galactose + Glucose | -1,4 | Yes | Milk sugar; galactose differs from glucose at C4 |
| Cellobiose | Glucose + Glucose | -1,4 | Yes | From cellulose hydrolysis |
C) DNA vs RNA
| Feature | DNA | RNA |
|---|---|---|
| Sugar | 2'-Deoxyribose | Ribose (2'-OH present) |
| Bases | A, T, G, C | A, U, G, C |
| Structure | Double helix | Usually single strand |
| Base pairing | A=T, G triple-bond C | A=U (when paired) |
| Location | Nucleus | Nucleus + cytoplasm |
| Function | Genetic information storage | Protein synthesis |
| Stability | More stable (no 2'-OH) | Less stable |
D) Vitamin Deficiency Diseases
| Vitamin | Chemical Name | Deficiency Disease |
|---|---|---|
| A | Retinol | Night blindness (Xerophthalmia) |
| B1 | Thiamine | Beriberi |
| B2 | Riboflavin | Cheilosis (cracked lips) |
| B12 | Cobalamin | Pernicious anemia |
| C | Ascorbic acid | Scurvy |
| D | Calciferol | Rickets (children), Osteomalacia (adults) |
| E | Tocopherol | Reproductive issues |
| K | Phylloquinone | Slow blood clotting |
| Niacin (B3) | Nicotinic acid | Pellagra |
| Folic acid | Pteroylglutamic acid | Megaloblastic anemia |
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