Most amino acid charts are copied from other amino acid charts. This one was computed, and then the method was checked against a molecule whose mass somebody else published — which is a slower way to make a table and the only way to know it is right.
The twenty
Codes follow the IUPAC-IUB conventions. Masses are average masses in daltons, computed from each molecular formula using standard atomic weights. The residue mass is the free amino acid minus one water — what the amino acid contributes once it is inside a chain.
| Name | 3-letter | 1-letter | Formula | Free (Da) | Residue (Da) |
|---|---|---|---|---|---|
| Glycine | Gly | G | C₂H₅NO₂ | 75.07 | 57.05 |
| Alanine | Ala | A | C₃H₇NO₂ | 89.09 | 71.08 |
| Serine | Ser | S | C₃H₇NO₃ | 105.09 | 87.08 |
| Proline | Pro | P | C₅H₉NO₂ | 115.13 | 97.12 |
| Valine | Val | V | C₅H₁₁NO₂ | 117.15 | 99.13 |
| Threonine | Thr | T | C₄H₉NO₃ | 119.12 | 101.11 |
| Cysteine | Cys | C | C₃H₇NO₂S | 121.15 | 103.14 |
| Leucine | Leu | L | C₆H₁₃NO₂ | 131.18 | 113.16 |
| Isoleucine | Ile | I | C₆H₁₃NO₂ | 131.18 | 113.16 |
| Asparagine | Asn | N | C₄H₈N₂O₃ | 132.12 | 114.10 |
| Aspartate | Asp | D | C₄H₇NO₄ | 133.10 | 115.09 |
| Glutamine | Gln | Q | C₅H₁₀N₂O₃ | 146.15 | 128.13 |
| Lysine | Lys | K | C₆H₁₄N₂O₂ | 146.19 | 128.18 |
| Glutamate | Glu | E | C₅H₉NO₄ | 147.13 | 129.12 |
| Methionine | Met | M | C₅H₁₁NO₂S | 149.21 | 131.19 |
| Histidine | His | H | C₆H₉N₃O₂ | 155.16 | 137.14 |
| Phenylalanine | Phe | F | C₉H₁₁NO₂ | 165.19 | 147.18 |
| Arginine | Arg | R | C₆H₁₄N₄O₂ | 174.20 | 156.19 |
| Tyrosine | Tyr | Y | C₉H₁₁NO₃ | 181.19 | 163.18 |
| Tryptophan | Trp | W | C₁₁H₁₂N₂O₂ | 204.23 | 186.21 |
Three things fall straight out of the table. The range is narrower than people expect — tryptophan is only about 3.3 times heavier than glycine, so peptides of similar length have similar masses regardless of composition. Leucine and isoleucine are identical in formula and in mass; they differ only in where the side chain branches, which is why no mass measurement can separate them. And only two residues contain sulphur, cysteine and methionine — cysteine's being the one that matters structurally, because it forms the disulphide bridges that hold folded molecules in shape.
The water, and the arithmetic everyone gets wrong
The most common mistake in checking a peptide's molecular weight is adding up its amino acids.
That answer is always too high, because forming a peptide bond releases a molecule of water. A chain of n residues has n − 1 bonds and has therefore shed n − 1 waters. At 18.015 daltons each, this is not a rounding error: a 30-residue peptide is about 522 daltons lighter than the sum of its parts.
So the working formula is:
peptide mass = Σ(residue masses) + 18.015
— the residue masses from the right-hand column, plus one water back for the two free ends of the finished chain.
Checking the method against something real
A table is only as good as its arithmetic, so here is the arithmetic run against a molecule whose mass was published by somebody else.
BPC-157, sequence GEPPPGKPADDAGLV — 15 residues, therefore 14 bonds.
| Step | Value |
|---|---|
| Sum of the 15 free amino acids | 1,671.77 Da |
| Less 14 × water (14 × 18.015) | − 252.21 Da |
| Computed mass | 1,419.56 Da |
| PubChem's stated mass (CID 9941957) | 1,419.5 Da |
They agree. The table and the method behind it reproduce an independently published figure to within the rounding, which is the only reason to trust either.
The same arithmetic run on C-peptide — 31 residues, EAEDLQVGQVELGGGPGAGSLQPLALEGSLQ — gives about 3,020 daltons, and anybody can repeat it with the column above.
The codes that are not amino acids
Four one-letter codes appear routinely in sequences and stand for no particular residue:
| Code | Means |
|---|---|
| B | Aspartate or asparagine (Asx) |
| Z | Glutamate or glutamine (Glx) |
| J | Leucine or isoleucine (Xle) |
| X | Any residue |
B and Z are historical honesty. A classical way of analysing composition converts asparagine to aspartate and glutamine to glutamate in the process of measuring them, so the method cannot distinguish the pairs — and rather than guessing, the notation records exactly what was established. J exists for the same reason at the mass-spectrometry end: leucine and isoleucine weigh the same, so an instrument reporting mass alone cannot choose between them.
A sequence containing B, Z, J or X is not a sequence with unusual chemistry in it. It is a sequence with a stated limit on what was measured.
Twenty, or twenty-two
The count depends on what is being counted, and the honest answer names the criterion.
Twenty is the standard set specified by the genetic code and present in essentially every protein — the table above.
Twenty-two adds two more that are genuinely incorporated during synthesis rather than attached afterwards, by machinery that reads what would otherwise be a stop codon:
- Selenocysteine (U) — cysteine with selenium in place of sulphur. Not a curiosity in humans: glutathione peroxidase 1 (UniProt P07203, 203 residues) carries one at position 49, written as a U in its own sequence.
- Pyrrolysine (O) — found in certain archaea and bacteria, not in humans.
Anything beyond that — hydroxyproline in collagen, phosphoserine in a signalling protein, the acetylated end of a synthetic peptide — is a modification, made after the chain is built. Modifications are extremely common and they change a molecule's mass, which is why a computed mass from this table sometimes disagrees with a published one. When it does, a modification is usually the reason, and the modification is usually the point of the molecule.
Why a library of compounds needs this page
Because nearly every claim about a peptide reduces to something in the table above. A sequence tells you its length; the residue masses tell you its weight; the weight tells you a great deal about whether it can survive a stomach or cross skin. The 500-dalton rule that governs what can be absorbed through skin is a statement about this column, and almost every peptide in this library is on the wrong side of it.
It also gives a reader something to check with. A vendor's certificate of analysis states a molecular weight. The sequence is usually published. Twenty numbers and one subtraction are enough to find out whether the two agree.
Related entries
What a peptide actually is · C-peptide, a 31-residue chain worked through end to end · BPC-157, the molecule used to check this table.
