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Peptide nomenclature, IUPAC reference

Amino acid codes
and notation.

The reference table of one-letter and three-letter codes for the twenty standard L-amino acids, plus notes on N-terminal and C-terminal modifications, salt forms, and post-translational modifications. The table working researchers reach for when reading a peptide sequence.

The twenty standard L-amino acids.

Each entry shows the full name, the standard three-letter code, the standard one-letter code, and key chemical properties. These are the codes used to write peptide sequences across all institutional and research literature. BPC-157’s sequence in one-letter code is GEPPPGKPADDAGLV; in three-letter code, the same sequence is Gly-Glu-Pro-Pro-Pro-Gly-Lys-Pro-Ala-Asp-Asp-Ala-Gly-Leu-Val. Both encode the same fifteen-amino-acid peptide.

Amino acid3-letter1-letterProperties
AlanineAlaAHydrophobic, small, neutral
ArginineArgRPositively charged, basic
AsparagineAsnNPolar, neutral
Aspartic acidAspDNegatively charged, acidic
CysteineCysCPolar, thiol-containing, disulfide bridge capable
Glutamic acidGluENegatively charged, acidic
GlutamineGlnQPolar, neutral
GlycineGlyGSmallest, no side chain
HistidineHisHPositively charged at low pH, aromatic, basic
IsoleucineIleIHydrophobic, branched chain
LeucineLeuLHydrophobic, branched chain
LysineLysKPositively charged, basic
MethionineMetMHydrophobic, sulfur-containing, oxidation-sensitive
PhenylalaninePheFHydrophobic, aromatic
ProlineProPImino acid, ring structure, conformationally rigid
SerineSerSPolar, hydroxyl-containing, phosphorylation site
ThreonineThrTPolar, hydroxyl-containing, phosphorylation site
TryptophanTrpWHydrophobic, aromatic, largest amino acid, fluorescent
TyrosineTyrYPolar, aromatic, hydroxyl-containing, phosphorylation site
ValineValVHydrophobic, branched chain

Sequence direction and termini.

Peptide sequences are written N-terminus to C-terminus by convention, left to right. The N-terminus is the free amine end (free -NH₂ group); the C-terminus is the free carboxyl end (free -COOH group). When a peptide is described as “N-terminally acetylated,” the free amine is replaced by -NH-CO-CH₃ (an acetyl group). When described as “C-terminally amidated,” the free carboxyl is replaced by -CO-NH₂ (a primary amide).

Modifications and prefixes.

Common modifications appear as prefixes or suffixes in peptide names. Ac- at the start indicates N-terminal acetylation. -NH₂ at the end indicates C-terminal amidation. D- before a residue indicates the D-stereoisomer (rare in biology, used in peptide engineering for protease resistance). p before a serine, threonine, or tyrosine indicates phosphorylation (e.g., pSer, pTyr).

Disulfide bridges and cyclization.

Disulfide bridges between two cysteine residues are denoted by brackets: (Cys^1-Cys^7) indicates a disulfide between cysteine residues at positions 1 and 7 of the sequence. Cyclized peptides are denoted by cyclo(...). Head-to-tail cyclization joins the N-terminus to the C-terminus.

Salt forms and counter-ions.

Peptide names sometimes include a salt-form designation: peptide.acetate, peptide.TFA, peptide.HCl, peptide.NH₄. Cresten Labs ships peptides as acetate salts by default. Alternate salt forms are available on quote.

Pyroglutamyl (pGlu) peptides.

When N-terminal glutamine (Gln, Q) or glutamic acid (Glu, E) is present, the residue can spontaneously cyclize to form pyroglutamate (pGlu). Pyroglutamyl peptides are denoted by pGlu- at the N-terminus or by (pyroglutamyl) notation. The pGlu form is reported as part of HPLC purity, not as an impurity, and is a stable, biologically relevant variant.

How a peptide name actually decodes.

Take a name like Ac-Gly-Pro-Glu-Lys-NH₂. Reading left to right: Ac- is N-terminal acetylation; Gly is glycine at position 1; Pro is proline at position 2; Glu is glutamic acid at position 3; Lys is lysine at position 4; -NH₂ is C-terminal amidation. Total: a four-residue peptide with both terminal modifications.