H-Lys(Me)2-OH · HCl

H-Lys(Me)2-OH · HCl is a lysine-derived amino acid hydrochloride in which the ε-amino side chain is dimethylated (Me)2, yielding a chiral, cationic amino acid salt with a free α-carboxylic acid and a protonated amine at the hydrochloride counterion. The structure contains an α-amino group that can be protected for peptide coupling, and a sterically hindered, tertiary ε-dimethylamino functionality that alters nucleophilicity and can modulate salt formation and chromatographic behavior. The presence of the carboxylic acid enables standard amide-bond formation chemistry, while the salt form supports handling as a stable intermediate for downstream derivatization. The dimethylated side chain can participate in alkylation, acylation, and quaternization-type transformations, making the compound relevant as a targeted lysine analog for peptide science and synthetic intermediate preparation.

1. Peptide Synthesis

H-Lys(Me)2-OH · HCl is used in peptide building block preparation where the α-carboxylic acid supports peptide coupling and the α-amino group can be protected (for example, via common N-protecting groups) to control chemoselectivity during stepwise synthesis. The dimethylated ε-amino side chain behaves differently from primary lysine, enabling selective functionalization strategies that can be exploited for orthogonal protection schemes and for tuning side-chain reactivity during N- and C-terminal modifications. The hydrochloride salt form can facilitate accurate weighing and reproducible salt-state behavior prior to conversion into coupling-ready protected derivatives. Peptide synthesis workflows can incorporate this lysine analog to generate defined side-chain sterics and tertiary amine character in linear peptides and peptide fragments for subsequent characterization or scaffold elaboration.

2. Chemical Biology Probes

H-Lys(Me)2-OH · HCl serves chemical biology research as a lysine-mimicking intermediate for constructing probes that incorporate a tertiary, dimethylated amine at the side-chain position. The tertiary amine can be leveraged for conjugation handles through acylation to form stable amides, formation of quaternary ammonium derivatives, or attachment of linkers designed for controlled ionization states in labeling reagents. The preserved carboxylic acid and protected α-amino chemistry allow incorporation into peptide conjugates, enabling side-chain-defined recognition motifs in biomolecular assays. Downstream probe generation can include peptide-based affinity reagents, labeling substrates, and structure-defined molecular tools that reflect lysine-like spacing while providing altered basicity and steric profiles.

3. Peptidomimetics And SAR

H-Lys(Me)2-OH · HCl is applied in peptidomimetic construction and structure-activity relationship studies where a lysine-derived stereocenter and a dimethylated ε-amine introduce controlled changes to hydrogen-bonding and conformational preferences. The tertiary amine functionality can be used to tune basicity and intramolecular interactions in peptide analogs, supporting rational design of analog series that probe side-chain effects on binding or activity trends. The amino acid backbone supports conversion into protected building blocks that undergo amide coupling to generate analogs with defined N-terminus and C-terminus patterns. Synthetic campaigns can use this chiral intermediate to prepare libraries of side-chain-modified peptide mimetics for SAR mapping and mechanistic studies of molecular recognition.

4. Side-Chain Functionalization

H-Lys(Me)2-OH · HCl is suitable for side-chain functionalization routes that capitalize on the tertiary dimethylamino group as a site for controlled derivatization. The ε-dimethylamino moiety can undergo quaternization to introduce permanent cationic centers, or can be acylated to generate N-acyl derivatives that modulate polarity and stability in downstream conjugates. The free α-carboxylic acid enables formation of activated esters or amide intermediates that can be carried into polymerizable or crosslinking chemistries when the α-amino functionality is appropriately protected. Industrial and research synthesis can employ the compound as a chiral lysine analog intermediate to access tertiary-amine-containing derivatives used in specialty chemical production and functional molecular design.

5. Pharmaceutical Intermediate Preparation

H-Lys(Me)2-OH · HCl is used in pharmaceutical intermediate preparation where a protected lysine-like scaffold with a tertiary ε-amine can support medicinal chemistry synthesis of amide-rich fragments and cationic side-chain motifs. The amino acid salt form provides a practical entry point for generating N-protected derivatives and for designing C-terminal transformations that feed into peptide-like or peptidomimetic intermediates. The dimethylated side chain can be carried through synthetic sequences as a stable tertiary amine, reducing the risk of primary amine overreactivity while still enabling targeted conversion to quaternary ammonium or acylated forms. Process-oriented workflows can incorporate the compound into fine chemical synthesis planning for defined chiral intermediates that maintain functional group compatibility across coupling and downstream derivatization steps.

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