L-Histidine

L‑Histidine is a proteinogenic, essential amino acid that contains an imidazole side chain, giving it unique chemical reactivity. It participates in protein synthesis, serves as a precursor for histamine and other bioactive molecules, and helps maintain cellular pH and metal‑ion homeostasis.

• IUPAC name: (2S)-2‑amino‑3‑(1H‑imidazol‑4‑yl)propanoic acid
• Molecular formula: C₆H₉N₃O₂ (M.W. ≈ 155.16 g·mol⁻¹)
• Structure:
  • A central α‑carbon bearing an amino group (–NH₂), a carboxyl group (–COOH), and an imidazole side chain (a five‑membered aromatic ring with two nitrogen atoms).
  • The imidazole provides a pKa near physiological pH, granting buffering capacity.
  • L‑Histidine is a zwitterion at neutral pH, soluble in water (≈ 100 g/L) and stable to pH 2–9.
  • The L‑configuration corresponds to the naturally occurring stereoisomer used in proteins.

• Natural Sources: Naturally, L‑histidine is abundant in meat, poultry, fish, dairy, eggs, legumes, and whole‑grain cereals.
• Commercial Production: Commercially, it is produced by fermentation of Corynebacterium glutamicum or E. coli strains engineered to over‑express histidine biosynthetic pathways, yielding a high‑purity, food‑grade product.
• Chemical Synthesis: Chemical synthesis (e.g., Strecker or Michael addition routes) is used for pharmaceutical‑grade material, but most supplement manufacturers prefer microbial fermentation because it yields a racemic mixture that is then resolved to the L‑form.
• Quality Markers: Quality markers include ≥ 99 % purity, low heavy‑metal content, and verification of the L‑isomer by chiral HPLC.
• Recommendations: Certified GMP facilities and third‑party testing (e.g., USP, NSF) are recommended to ensure consistency and safety.