L-Ornithine ethyl ester dihydrochloride is a protected amino acid derivative in which the side chain of L-ornithine contains a terminal primary amine and the carboxyl group is converted to an ethyl ester, yielding a molecule with both amino and ester functionalities. The compound is present as a dihydrochloride salt, with chloride counterions associated to protonated basic groups, and retains the amino group on the α-position while the side-chain amine provides a second basic site for salt formation and subsequent derivatization. In peptide and chemical biology workflows, this esterified, salt-form amino acid is used as a precursor for stepwise synthesis and for preparing ornithine-containing building blocks or conjugates where controlled handling of the carboxyl group and the two amine functionalities is required.
CAT No: CP08731
CAS No:84772-29-2
Synonyms/Alias:84772-29-2;(S)-Ethyl2,5-diaminopentanoatedihydrochloride;EthylL-ornithinedihydrochloride;L-OrnithineEthylesterDihydrochloride;EthylL-ornithineHCl;SCHEMBL11191636;CTK7E7318;MolPort-020-001-686;EINECS283-859-6;KM2227;SBB070614;AKOS015902235;AC-7490;AM82631;AN-8975;AK111192;KB-53344;ST24036283;X4052;A840911;ethyl(2S)-2,5-diaminopentanoatedihydrochloride;I14-2788;W-104107;ethyl(2S)-2,5-bis(azanyl)pentanoatedihydrochloride;I14-13719
L-Ornithine ethyl ester dihydrochloride is a chiral amino acid ester derived from L-ornithine, featuring a primary amine side chain and an esterified carboxyl group, both present as dihydrochloride salts that enhance handling and aqueous compatibility. The molecule bears two basic nitrogens capable of forming stable salts and participating in selective protection/deprotection logic during synthesis. The ethyl ester functionality enables controlled conversion to carboxylic acid derivatives or activated intermediates, while the stereogenic center at the α-carbon preserves L-configuration for downstream peptide and peptidomimetic construction. Salt-state protonation and the ester group together shape a reactivity profile suited to amino acid derivatization, coupling chemistry, and stepwise industrial intermediate preparation.
1. Protected Amino Acid Synthesis
L-Ornithine ethyl ester dihydrochloride supports protected amino acid synthesis workflows in fine chemical and peptide-manufacturing settings, where orthogonal protection of the α-amino group and the side-chain primary amine is required. The ethyl ester can be retained during early protection steps and later converted to an acid or activated derivative for coupling, while the dihydrochloride salt form helps manage amine reactivity and improves reproducibility in multistep sequences. Side-chain and α-amino functional groups can be selectively masked using standard amino-protecting-group strategies to enable controlled peptide coupling chemistry without cross-reactivity. Downstream, the protected ornithine ester serves as a chiral intermediate for assembling ornithine-containing peptides and for preparing amino acid building blocks used in synthetic methodology development and applied manufacturing routes.
2. Peptide Synthesis
L-Ornithine ethyl ester dihydrochloride is applicable to peptide synthesis and peptidomimetic construction where an ornithine residue with a protected side-chain amine is incorporated into growing chains. The L-configuration at the α-carbon provides stereochemical fidelity for peptide backbone formation, while the side-chain primary amine enables formation of amide linkages after appropriate protection and activation of the carboxyl component. Esterification as an ethyl ester can be leveraged during intermediate preparation to generate activated carboxyl derivatives for coupling, then transformed to the corresponding acid form when the final peptide bond-forming step requires it. Resulting ornithine-containing sequences can be used as biochemical research reagents, scaffold components for SAR studies, and synthetic intermediates for producing structured peptide analogs with defined side-chain functionality.
3. Bioconjugation Chemistry
L-Ornithine ethyl ester dihydrochloride can be employed in bioconjugation chemistry and chemical biology workflows that require introduction of an ornithine-derived amine handle into biomolecule scaffolds. The presence of two amine functionalities allows design of conjugation strategies where one amine is selectively protected or functionalized, enabling controlled attachment to activated esters, isothiocyanates, aldehyde-derived linkers, or other electrophiles used for biomolecule labeling. The ester group supports conversion to carboxyl-activated intermediates when a spacer or coupling arm must be generated from the same chiral starting material. Ornithine-derived conjugates can then be used for probe construction, affinity reagent preparation, and labeling chemistry that depends on predictable amine positioning and stereochemical consistency from the L-configuration.
4. Process Chemistry Intermediate
L-Ornithine ethyl ester dihydrochloride serves as a process chemistry intermediate for industrial fine chemical synthesis, particularly where stable, salt-form amino acid esters are advantageous for handling and feedstock consistency. The dihydrochloride salt form mitigates issues related to free-base amine volatility and can improve solubility during upstream transformations, while the ester functionality provides a controllable handle for sequential conversion to carboxylic acid derivatives. The molecule's bifunctional amine pattern supports manufacturing route design that includes selective protection, activation, and coupling steps to produce ornithine-based building blocks at scale. Downstream, the intermediate can be directed toward production of ornithine-containing peptide fragments, amino acid derivatives for specialty chemical production, and chiral inputs for continued synthetic sequences in industrial amino acid chemistry.
5. Analytical Research Standards
L-Ornithine ethyl ester dihydrochloride is suitable for analytical research and method development where chiral amino acid ester standards or reference materials are required to monitor derivatization, protection efficiency, and conversion to acids or activated species. The defined stereochemistry of the L-α-carbon center and the presence of amine groups enable consistent chromatographic and mass spectrometric behavior after salt dissociation and derivatization steps. The ester group provides an additional chemical signature that can be tracked during process monitoring, including transitions to carboxylate forms used in peptide coupling workflows. Reference use of ornithine-derived esters supports quality control of amino acid intermediate preparation, verification of structural integrity in synthetic sequences, and calibration of analytical methods for amino acid ester and protected amino acid intermediates.
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