L-δ-Hydroxylysine HCl is a free, naturally occurring amino acid derivative in which the side chain of lysine bears a δ-hydroxyl substituent, with an amino group and a carboxyl group characteristic of amino acids. The molecule is present as a hydrochloride salt, pairing the basic side-chain functionality with chloride, and it retains the L stereochemical designation indicated in the name. L-δ-Hydroxylysine HCl is used as a chemically defined building block for peptide and protein-analog synthesis, for preparing hydroxylated lysine-containing peptide motifs, and for analytical or labeling workflows that require a lysine hydroxylation handle.
CAT No: CP07101
L-δ-Hydroxylysine HCl is the hydrochloride salt of the L-configured amino acid bearing a side-chain δ-hydroxyl group on the lysine carbon skeleton, providing an additional alcohol functionality beyond the primary ε-amino handle. The molecule contains an amino group and a carboxylic acid (present as the salt form), with stereochemical definition at the α-carbon that governs peptide stereochemistry and downstream recognition. The δ-hydroxyl can participate in hydrogen bonding and can be selectively protected or converted to activated derivatives, while the ε-amino group enables orthogonal protection strategies for controlled peptide coupling and selective functional group transformations. As a chiral amino acid intermediate, L-δ-Hydroxylysine HCl is suitable for incorporation into peptide building blocks and for manufacturing routes that require hydroxylated lysine motifs for biochemical probes, synthetic biology constructs, and fine chemical derivatization.
1. Peptide Synthesis
L-δ-Hydroxylysine HCl is used in peptide synthesis workflows where hydroxylated lysine residues are required to model post-translational modifications and to generate peptide building blocks with defined side-chain functionality. The protected amino acid derivative strategy typically targets the α-amino and carboxyl groups for coupling, while orthogonal protection of the δ-hydroxyl and ε-amino groups can enable selective deprotection and sequential functionalization. Side-chain hydroxyl presence supports hydrogen-bonding patterns and can be maintained, activated, or transformed during peptide assembly to produce hydroxylysine-containing analogs. Downstream peptide products can serve as standards for method development, as substrates for enzyme studies, or as scaffold components in peptidomimetic construction.
2. Chemical Biology Probes
L-δ-Hydroxylysine HCl is applied in chemical biology research to access hydroxylated lysine motifs for recognition studies, affinity probes, and substrate analogs used to probe enzyme specificity toward hydroxylysine chemistry. The δ-hydroxyl group enables controlled derivatization to linkers, reactive handles, or masked functionalities, while the ε-amino functionality can be protected to preserve chemoselectivity during probe synthesis. Salt formation with HCl supports handling as a well-defined chiral amino acid intermediate that can be converted into protected derivatives for downstream conjugation chemistry. Resulting hydroxylysine-bearing probes can be employed in biochemical assays, molecular recognition experiments, and structural studies that require stereochemically consistent amino acid incorporation.
3. Bioconjugation Chemistry
L-δ-Hydroxylysine HCl is suitable for bioconjugation chemistry where hydroxylated lysine residues are introduced as defined attachment points for linker installation and biomolecule modification. The side-chain δ-hydroxyl can be functionalized into activated intermediates or protected forms that withstand coupling conditions, while the ε-amino group can be selectively masked to prevent uncontrolled crosslinking. Orthogonal protection and deprotection strategies allow sequential modification, enabling construction of conjugates with controlled substitution patterns and preserved stereochemistry at the α-center. Hydroxylysine-containing conjugates can be used to generate labeled peptides, functional biomolecule derivatives, and analytical reagents for monitoring conjugation outcomes.
4. Enzyme Studies
L-δ-Hydroxylysine HCl is employed in enzyme studies and mechanistic investigations that require hydroxylated lysine substrates or inhibitors to evaluate catalytic tolerance and binding-site interactions. The molecule's δ-hydroxyl and ε-amino groups provide functional groups that can mimic natural hydroxylysine behavior in enzyme active sites, while the L-configuration supports stereochemical fidelity for substrate recognition. Protected amino acid synthesis routes enable preparation of peptide or small-molecule derivatives that present the hydroxylysine side chain in a defined context, including C-terminal or N-terminal modifications for assay compatibility. Downstream derivatives can function as analytical standards, kinetic substrates, or structure-matched analogs used to interpret enzyme specificity and transformation pathways.
5. Pharmaceutical Intermediate Preparation
L-δ-Hydroxylysine HCl is relevant to pharmaceutical intermediate preparation and fine chemical synthesis where hydroxylated lysine building blocks are required for peptide-based drug candidates, peptidomimetics, or stereochemically defined pharmacophores. The amino acid's carboxyl and amino functionalities support conversion into coupling-ready protected forms, while the δ-hydroxyl enables controlled functional group manipulation for linker installation, solubility tuning, or scaffold elaboration. Salt handling and chiral integrity support reliable downstream processing into protected amino acid derivatives that participate in peptide coupling chemistry under standard synthetic conditions. Resulting hydroxylysine-containing intermediates can be incorporated into manufacturing-oriented synthetic sequences to produce research-grade and process-compatible peptide analogs for medicinal chemistry and SAR studies.
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