L-Ornithine methyl ester dihydrochloride is a protected amino acid ester derived from the basic amino acid ornithine, featuring a methyl ester at the carboxyl terminus and an unprotected primary amino group on the side chain. The molecule is present as a dihydrochloride salt, with two chloride counterions associated to protonated amino functionalities, and it retains the L-stereochemical designation indicated in the product name. In peptide and amine-derivative synthesis, this esterified, salt-form ornithine analogue functions as a precursor for preparing ornithine-containing building blocks, as well as for chemical labeling or conjugation workflows that require a protected carboxyl group while retaining side-chain amine reactivity.
CAT No: CP08732
CAS No:40216-82-8
Synonyms/Alias:40216-82-8;H-Orn-OMe.2HCl;L-OrnithineMethylesterDihydrochloride;H-ORN-OME2HCL;(S)-Methyl2,5-diaminopentanoatedihydrochloride;MethylL-ornithinedihydrochloride;MethylL-ornithineHCl;H-Orn-OMe?HCl;H-Orn-OMe??2HCl;PubChem18996;H-Orn-OMeinvertedexclamationmarkcurrency2HCl;H-Orn-OMedihydrochloride;KSC491O3L;SCHEMBL4806054;CTK3J1735;MolPort-003-894-334;SNFZNVWAQDVFAK-XRIGFGBMSA-N;EINECS254-841-5;ANW-43149;CH-332;ornithinemethylesterdihydrochloride;AKOS015907728;AKOS015924229;RTR-016058;AK-41688
L-Ornithine methyl ester dihydrochloride is the methyl ester hydrochloride salt of L-ornithine, featuring the amino acid backbone with a side chain bearing an additional primary amine at the δ-position. The molecule exists as a dihydrochloride, so both the α-amino and the side-chain amino groups are present in protonated, salt-stabilized form, while the carboxyl functionality is masked as a methyl ester that can be selectively transformed under standard amino acid chemistry conditions. The stereogenic center at the α-carbon is set to the L-configuration, enabling predictable stereochemical outcomes during downstream derivatization and peptide-relevant coupling. The combination of an ester and two amines makes the compound a practical chiral building block for protected amino acid synthesis, orthogonal functionalization, and conversion into free acids, amides, or N-functional derivatives.
1. Protected Amino Acid Synthesis
L-Ornithine methyl ester dihydrochloride supports protected amino acid synthesis workflows where the side-chain primary amine and the α-amino group must be controlled independently. The methyl ester provides a handle for C-terminal activation or conversion to an acid equivalent, while the dihydrochloride salt form can be used to manage amine protonation during protection-group installation and subsequent coupling steps. Selective N-protection strategies can generate mono- or orthogonally protected ornithine derivatives that participate in peptide coupling chemistry with reduced risk of uncontrolled polyamidation. The resulting protected ornithine intermediates can be carried forward into peptidomimetic construction and synthetic methodology studies focused on amine-rich residues.
2. Peptide Coupling Chemistry
L-Ornithine methyl ester dihydrochloride is applicable to peptide synthesis planning where an ornithine residue is required as a cationic, side-chain-functional amino acid building block. The two amines enable formation of amide linkages at the α-position after appropriate activation of the ester-derived carboxyl functionality, while the side-chain amine can be preserved, protected, or converted to a desired derivative for later steps. Ester-to-acid conversion strategies and N-protection/deprotection sequences can be integrated to align with common peptide coupling compatibility, including chemoselective handling of nucleophilic sites. The ability to incorporate a defined L-ornithine stereocenter supports the preparation of analog peptides and peptide fragments used in biochemical research and structure-activity relationship studies.
3. Chemical Biology Conjugation
L-Ornithine methyl ester dihydrochloride can be used in chemical biology to generate amine-reactive or amine-bearing intermediates for biomolecule modification. The salt-stabilized primary amines facilitate controlled derivatization into N-functional groups that can later participate in conjugation chemistries, including linker installation for attaching to proteins, peptides, or nucleic-acid analogs. The methyl ester can be transformed to carboxyl or amide functionalities, enabling the construction of conjugation handles with defined spacing and charge properties. Downstream products may serve as labeling reagents, affinity probes, or scaffold components in studies of molecular recognition that depend on the cationic character of ornithine side chains.
4. Process Chemistry Intermediate
L-Ornithine methyl ester dihydrochloride is suitable for process chemistry intermediate preparation due to its clear functional-group inventory and controllable salt form. The L-configuration provides a consistent chiral starting point for stereochemically defined downstream intermediates, while the methyl ester can be converted to activated acid forms or used as an ester-stage handle in manufacturing sequences. Dual amine functionality supports formation of protected derivatives that can be manufactured as discrete, isolable intermediates, enabling route design that manages chemoselectivity and reduces side reactions from free polyamines. The compound's compatibility with standard amino acid protection strategies makes it relevant for specialty chemical production and fine chemical synthesis where ornithine-derived building blocks are required at scale.
5. Peptidomimetics And SAR Studies
L-Ornithine methyl ester dihydrochloride supports peptidomimetic construction where a side-chain primary amine is used to tune charge, hydrogen-bonding patterns, and conformational preferences in bioactive scaffolds. The combination of an ester-derived carboxyl handle and an L-ornithine stereocenter enables systematic generation of N-substituted or side-chain-modified analogs that can be incorporated into peptide-like structures or cyclic/branched mimetics. Orthogonal protection strategies can allow sequential functionalization, supporting SAR-focused synthesis campaigns that require controlled variation of amine substituents and linkage types. Ornithine-derived mimetic intermediates prepared from this compound can be used to build libraries for analytical characterization and structure-function investigations in applied medicinal chemistry research.
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