H-trans-4,5-Dehydro-DL-Lys-OH · 2 HCl

H-trans-4,5-Dehydro-DL-Lys-OH · 2 HCl is a dehydro-analog of lysine provided as a dihydrochloride salt, featuring a protected-free amino acid framework with two amine hydrochloride functionalities and a trans-configured 4,5-unsaturation in the side chain. The molecule retains the canonical amino acid stereochemical motif at the α-carbon while introducing a rigidified alkenyl segment that can participate in stereodefined transformations distinct from saturated lysine. The salt form increases water compatibility and supports handling in peptide coupling and salt-stabilized intermediate workflows, while the free carboxylic acid enables standard activation chemistries. The combination of a chiral amino acid core and an alkene-containing side chain makes the compound a useful chiral amino acid intermediate and peptide building block for constructing constrained lysine-derived motifs.

1. Peptide Synthesis

H-trans-4,5-Dehydro-DL-Lys-OH · 2 HCl supports peptide building block preparation where lysine-like side-chain chemistry is required but with an alkene handle for downstream diversification. The α-carboxylic acid and salt-stabilized amine functionality enable coupling to activated carboxyl partners under peptide synthesis conditions, while the trans-4,5-dehydro side chain can be preserved or selectively transformed after chain assembly. Side-chain unsaturation can be leveraged for post-coupling functionalization such as selective addition reactions or oxidative conversions that generate new functional groups on the lysine scaffold. The resulting peptide analogs are suitable for mapping how constrained lysine geometry influences backbone/side-chain recognition in biochemical research and structure-activity relationship studies.

2. Amino Acid Modification

H-trans-4,5-Dehydro-DL-Lys-OH · 2 HCl is suitable for amino acid derivatization programs aimed at introducing an alkene-bearing lysine motif for controlled functional group installation. The trans-dehydro segment provides a defined stereochemical element that can undergo addition, cycloaddition, or oxidation to furnish aldehyde, ketone, or substituted alkyl/heteroatom-containing derivatives depending on the chosen transformation. The presence of the carboxylic acid and amino groups supports formation of amide, ester, or protected amine intermediates, enabling stepwise protection-group strategies for selective reactivity. Downstream products can serve as chemical biology probes, peptide side-chain surrogates, or process intermediates for fine chemical synthesis where stereodefined unsaturation is a key design feature.

3. Peptidomimetics And SAR

H-trans-4,5-Dehydro-DL-Lys-OH · 2 HCl can be applied in peptidomimetic construction where lysine-derived pharmacophores are engineered to impose conformational constraints. The trans-configured 4,5-unsaturation in the side chain can mimic or tune spatial presentation relative to native lysine, supporting SAR studies that compare saturated versus dehydro analogs of peptide ligands. The amino acid core allows incorporation into peptide scaffolds or conversion into non-natural side-chain-modified residues, while the carboxyl group and amine functionality facilitate attachment to scaffold backbones and linker chemistry. The resulting constrained analog series can be used to generate structure-defined libraries for molecular design and binding-site interrogation in biochemical and medicinal chemistry workflows.

4. Chemical Biology Probes

H-trans-4,5-Dehydro-DL-Lys-OH · 2 HCl enables chemical biology research requiring a lysine-like residue with a reactive side-chain alkene for probe installation. The dihydrochloride salt form provides consistent handling of the amino acid during labeling workflows and can support controlled protection-group strategies for selective coupling to biomolecules or probe scaffolds. The trans-dehydro side chain can serve as a functional handle for conjugation chemistry after peptide or linker assembly, allowing formation of covalent adducts or incorporation of reporter-bearing substituents. The compound's stereochemical side-chain constraint can improve interpretability of labeling experiments by reducing conformational heterogeneity in biomolecule-bound states.

5. Pharmaceutical Manufacturing Intermediates

H-trans-4,5-Dehydro-DL-Lys-OH · 2 HCl is suitable as a process chemistry intermediate for manufacturing peptide-based or peptide-derived intermediates that require a dehydro-lysine residue. The amino acid salt form improves operational robustness during solution-phase handling, while the free carboxylic acid supports standardized activation and coupling steps in controlled synthesis of dehydro-containing intermediates. The trans-alkene side chain can be carried through early manufacturing stages and converted in later steps to generate defined functional groups needed for downstream purification, formulation compatibility, or final scaffold assembly. The compound's role as a chiral amino acid intermediate aligns with industrial fine chemical synthesis routes that rely on stereochemically defined building blocks for consistent product profiles.

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