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L(+)-Ornithine hydrochloride is the hydrochloride salt form of the naturally occurring L-enantiomer of the amino acid ornithine (chemical formula: C₅H₁₃ClN₂O₂).
Ornithine: A non-proteinogenic amino acid (C₅H₁₂N₂O₂), crucial in the urea cycle for detoxifying ammonia and a precursor to compounds like arginine and polyamines.
L(+): Specifies the biologically active, "left-handed" stereoisomer that is dextrorotatory (+).
Hydrochloride (HCl): The salt form improves water solubility and stability. The free base's two amino groups bind HCl, forming a crystalline powder (⁺H₃N-CH₂-CH₂-CH₂-CH(NH₃⁺)-COOH Cl⁻).
It's used clinically and in supplements due to its solubility.
L(+)-Ornithine hydrochloride is the hydrochloride salt of the naturally occurring L-enantiomer of the amino acid ornithine. Here's a detailed chemical breakdown:
Ornithine:
Chemically known as 2,5-diaminopentanoic acid.
Formula: C₅H₁₂N₂O₂
Structure: H₂N-CH₂-CH₂-CH₂-CH(NH₂)-COOH
A non-proteinogenic (not directly incorporated into proteins during synthesis) α-amino acid.
Plays a crucial role in biological systems, primarily in the urea cycle where it helps convert toxic ammonia into urea for excretion. It's also a precursor to amino acids like arginine, proline, and polyamines (e.g., putrescine, spermidine, spermine).
L(+) Enantiomer:
L: This specifies the stereochemistry (chirality) at the α-carbon atom (the carbon adjacent to the carboxyl group -COOH). The "L" designation refers to the absolute configuration similar to L-glyceraldehyde. In biological systems, amino acids are almost exclusively found in the L-form and are the physiologically active form. L-Ornithine is the natural form involved in the urea cycle.
(+): This indicates the compound is dextrorotatory, meaning it rotates the plane of plane-polarized light to the right (clockwise). While most L-amino acids are dextrorotatory (+), this is not an absolute rule (e.g., L-alanine is (+), L-serine is (+), but L-arginine is (-)). For L-ornithine, the specific rotation is positive.
Hydrochloride Salt (HCl):
Solubility: Makes them highly soluble in water, which is crucial for biological applications and formulation (e.g., in IV solutions or supplements).
Stability: Enhances crystalline stability and shelf life.
Handling: Creates a stable, typically crystalline solid.
This means the ornithine molecule is combined with hydrochloric acid (HCl).
Ornithine has two amino groups (one α-amino and one side-chain δ-amino) and one carboxyl group. In aqueous solution near physiological pH, it exists as a dication (H₃N⁺-CH₂-CH₂-CH₂-CH(NH₃⁺)-COOH), carrying two positive charges.
The hydrochloride salt is formed when the free base form of L-ornithine (which has one amino group deprotonated, typically H₂N-CH₂-CH₂-CH₂-CH(NH₃⁺)-COO⁻, making it a zwitterion with a net +1 charge) reacts with HCl. This protonates the second amino group, forming the dication, and adds a chloride anion (Cl⁻) as the counterion to achieve electrical neutrality.
Formula: C₅H₁₂N₂O₂ · HCl (Often written as C₅H₁₃ClN₂O₂ to show the protonated state)
Why a salt? Converting amino acids to their hydrochloride salts significantly improves:
Summary:
L(+)-Ornithine hydrochloride is the water-soluble hydrochloride salt of the naturally occurring, biologically active, dextrorotatory enantiomer of the amino acid ornithine. Its chemical structure is best represented as:
[⁺H₃N-CH₂-CH₂-CH₂-CH(NH₃⁺)-COOH] Cl⁻
Key Characteristics:
Chemical Name: (S)-2,5-Diaminopentanoic acid hydrochloride
Molecular Formula: C₅H₁₃ClN₂O₂
CAS Number: 3184-13-2
Appearance: Typically a white crystalline powder.
Solubility: Highly soluble in water.
Role: Important intermediate in metabolism (urea cycle, arginine/polyamine synthesis), used in research, clinical nutrition (e.g., liver support), and sometimes in dietary supplements (e.g., athletic performance). The hydrochloride form ensures good solubility for these applications.
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