Life Sciences · Biochemistry

Amino
Acids

The molecular alphabet of life — 21 building blocks that link together to form every protein in your body, from your hair to your enzymes to the antibodies in your blood.

21 Proteinogenic 9 Essential Peptide Bonds 4 Categories

3D model: Edumol on Sketchfab

Structure

Anatomy of an amino acid

Every amino acid shares the same core backbone — the unique R group (side chain) is what makes each one different.

O⁻ O C H NH₃⁺ R CARBOXYL AMINO R GROUP
Carboxylic acid group (–COOH) Acts as an acid — donates a proton. At body pH 7.4 it exists as –COO⁻ (deprotonated). This end links to the next amino acid via a peptide bond.
Amino group (–NH₂) Acts as a base — accepts a proton. At body pH appears as –NH₃⁺. This end receives the peptide bond when two amino acids connect.
Alpha carbon (Cα) The central carbon bonded to all four groups. In all amino acids except glycine it is a chiral center — the four different groups make it asymmetric.
R group (side chain) The variable part. It determines each amino acid's chemical personality — size, charge, polarity, and how it interacts with water or other molecules.

Explorer

The 21 proteinogenic amino acids

Tap any card for details. The standard genetic code encodes 20; selenocysteine (Sec/U) is the 21st.

A. Electrically Charged Side Chains

These side chains carry a net charge at physiological pH 7.4. Charged amino acids are often found on protein surfaces, where they interact with water and other charged molecules.

Positively charged (+)
ArgR
Arginine
Guanidinium side chain; pKa 12.1
HisH
Histidine
Imidazole ring; pKa 6.0; often at active sites
Essential
LysK
Lysine
Long chain with –NH₃⁺ tip; pKa 10.7
Essential
Negatively charged (−)
AspD
Aspartic Acid
Short –CH₂–COO⁻; pKa 3.7
GluE
Glutamic Acid
Longer –(CH₂)₂–COO⁻; pKa 4.15
B. Polar Uncharged Side Chains

These side chains form hydrogen bonds with water but carry no net charge. They are often found in enzyme active sites or on protein surfaces.

SerS
Serine
Hydroxyl –OH; phosphorylation site
ThrT
Threonine
–OH with methyl branch
Essential
AsnN
Asparagine
Amide –CONH₂; H-bond donor & acceptor
GlnQ
Glutamine
Longer amide chain; nitrogen transport
C. Special Cases

Each of these breaks a rule: glycine has no chirality, proline forms a ring with the backbone, cysteine forms disulfide bridges, and selenocysteine uses the rare element selenium.

CysC
Cysteine
–SH thiol; forms –S–S– bridges; pKa 8.1
SecU
Selenocysteine
–SeH; 21st amino acid; UGA codon
GlyG
Glycine
R = H; only achiral amino acid
ProP
Proline
Pyrrolidine ring; introduces kinks in chains
D. Hydrophobic Side Chains

These side chains avoid water and cluster together in a protein's core, driving folding. They are the "greasy" glue that holds protein 3-D structure together.

AlaA
Alanine
Methyl –CH₃; smallest hydrophobic R
ValV
Valine
Branched 3-carbon; often in β-sheets
Essential
IleI
Isoleucine
Two branches; 4 carbons
Essential
LeuL
Leucine
Branched; most common in proteins
Essential
MetM
Methionine
Sulfur in chain; start codon (AUG)
Essential
PheF
Phenylalanine
Benzene ring; bulky aromatic
Essential
TyrY
Tyrosine
Phe + –OH; both aromatic & polar
TrpW
Tryptophan
Indole ring; precursor to serotonin
Essential

Bonding

Peptide bonds: linking amino acids

A peptide bond forms when the carboxyl group of one amino acid reacts with the amino group of another, releasing a water molecule (condensation reaction).

  1. 1

    Two amino acids align: the –COOH of amino acid 1 faces the –NH₂ of amino acid 2.

  2. 2

    A condensation reaction occurs — the –OH from the carboxyl and an –H from the amino group combine and leave as water (H₂O).

  3. 3

    A covalent C–N peptide bond forms between the two residues. The linked pair is called a dipeptide.

  4. 4

    The process repeats at both ends, growing the chain into a polypeptide. Hundreds or thousands of amino acids can link this way.

Condensation reaction Amino Acid 1 H₂N–Cα– COOH Amino Acid 2 H₂N –Cα–COOH react …–Cα–CO–NH–Cα–… peptide bond + H₂O released + H₂O ↑ (released)
Chains of 2–49 residues = peptide. 50+ residues = polypeptide. A folded polypeptide = protein.

Interactive Lab

Build a peptide chain

Click amino acids to add them to your chain. Peptide bonds form automatically between each residue.

Amino acid palette
Click amino acids to start your chain →
Add amino acids to see chain properties.

Nutrition

The 9 essential amino acids

Your body cannot synthesize these — they must come from food. Complete protein sources (meat, fish, eggs, soy, quinoa) contain all nine.

HistidineHis · H
Makes histamine; important for immune response and stomach acid production.
IsoleucineIle · I
BCAA; involved in muscle metabolism and energy regulation.
LeucineLeu · L
Most abundant BCAA; triggers muscle protein synthesis (mTOR pathway).
LysineLys · K
Required for collagen and carnitine synthesis; supports calcium absorption.
MethionineMet · M
Start codon; methyl donor for epigenetics; precursor to cysteine.
PhenylalaninePhe · F
Precursor to tyrosine, dopamine, and norepinephrine.
ThreonineThr · T
Supports gut mucus layer; precursor to glycine and serine.
TryptophanTrp · W
Sole precursor to serotonin and melatonin — mood and sleep.
ValineVal · V
BCAA; fuel source for muscles during exercise; cognitive function.

Beyond Structure

What amino acids do beyond proteins

🧠 Neurotransmitter biosynthesis

Tryptophan → serotonin & melatonin. Tyrosine → dopamine & norepinephrine. Glutamate itself is the brain's main excitatory neurotransmitter.

Metabolism & energy

Amino acids can be broken down (catabolized) for energy when carbohydrates are scarce. Alanine shuttles nitrogen from muscle to liver during fasting.

🔬 Signaling & regulation

Serine and threonine are phosphorylated by kinases to switch proteins on/off. Tyrosine is targeted in major receptor pathways (insulin, growth factors).

🛡️ Antioxidant defense

Cysteine is a key component of glutathione — the cell's primary antioxidant. Selenocysteine in glutathione peroxidase destroys reactive oxygen species.

🔗 Structural roles

Glycine is ~35% of collagen by mass. Proline creates structural "kinks" in collagen's triple helix. Cysteine disulfide bridges stabilize keratin (hair, nails).

🧬 Epigenetics

Methionine is the universal methyl group donor via S-adenosylmethionine (SAM). DNA methylation — a key epigenetic mark — depends on adequate methionine intake.

Reflect

Discussion questions