L-Lysine monohydrate is the monohydrate form of the proteinogenic amino acid L-lysine, featuring a primary amino group on the side chain (ε-amino) attached to a five-carbon aliphatic chain and a carboxylic acid on the α-carbon. The molecule contains an α-amino group and a carboxyl group, and the lysine side chain bears a basic functionality that can form salts or engage in acid-base equilibria, while the monohydrate indicates association with water in the solid state. L-Lysine monohydrate is used as a free amino acid building block for peptide synthesis workflows and as a substrate or reference material in analytical method development where the defined lysine functional groups and stereochemistry are required.
CAT No: CP01407
CAS No:39665-12-8
Synonyms/Alias:L-Lysinehydrate;L-Lysinemonohydrate;39665-12-8;Lysinemonohydrate;H-Lys-OHH2O;lysine,hydrate;UNII-F7625B974U;SBB062982;lysinehydrate;L(+)-Lysinemonohydrate;L-Lysine,hydrate;l-Lysine,monohydrate;H-Lys-OH??H2O;L-2,6-Diaminohexanoicacid;l-Lysine,hydrate(1:1);SCHEMBL318676;282677_ALDRICH;C6H16N2O3;CTK0A0010;HZRUTVAFDWTKGD-JEDNCBNOSA-N;MolPort-003-929-177;ANW-60713;MFCD00151035;(S)-2,6-Diaminocaproicacidhydrate;AKOS005145556
L-Lysine monohydrate is the hydrated form of the essential amino acid L-lysine, featuring a primary aliphatic amino group at the side chain and a second amino functionality at the alpha position along with a carboxylic acid. The molecule is chiral at the alpha carbon (L-configuration) and exists as a salt-like hydrate that can influence handling, dissolution, and downstream salt formation. Lysine's side-chain ε-amine and alpha-carboxyl group provide a strong reactivity profile for derivatization, including amide formation, carbamate formation, and selective protection/deprotection strategies that are central to protected amino acid synthesis. The monohydrate form is commonly treated as a practical, weighable precursor to lysine derivatives and peptide building blocks, supporting conversion into N- and C-functionalized intermediates for peptide coupling and industrial chemical manufacturing routes.
1. Peptide Synthesis
L-Lysine monohydrate supports peptide building block preparation through its dual amino functionality, enabling controlled formation of N- and C-terminal lysine derivatives prior to amide bond construction. Lysine's ε-amine can be protected as an orthogonally removable group to prevent side reactions during coupling, while the alpha-carboxyl group participates in standard peptide coupling chemistries after conversion to an activated acid derivative. The L stereocenter is retained through appropriate protection and activation sequences, supporting stereochemically defined peptide assembly for research-grade peptide libraries. Downstream lysine-containing peptides and peptidomimetics can be generated after deprotection and sequential coupling steps, making the monohydrate a direct entry point to protected lysine building blocks and side-chain functional peptide analogs.
2. Chemical Biology
L-Lysine monohydrate is used in chemical biology workflows where amino acid derivatization and controlled conjugation are required to probe biomolecular interactions. The ε-amine enables formation of amide and urea linkages, as well as attachment of electrophilic tags, fluorophores, affinity handles, or crosslinking moieties after converting lysine into a protected or activated intermediate. The presence of both alpha and side-chain functional groups allows selective targeting strategies when orthogonal protecting-group schemes are applied to distinguish backbone from side-chain reactivity. Lysine-derived conjugates can serve as substrates, mimics, or labeling reagents in studies of protein modification, binding-site mapping, and biomolecule recognition, aligning with peptide science and amino acid chemistry needs for defined functional group placement.
3. Bioconjugation Chemistry
L-Lysine monohydrate functions as a starting material for bioconjugation reagents that rely on nucleophilic amine chemistry for stable linkage formation. The ε-amine can be transformed into N-hydroxysuccinimide-type active esters, carbamates, or amide-forming intermediates through appropriate activation and protection logic, enabling coupling to carboxylate- or amine-bearing biomolecules. The L-configuration and amino acid backbone identity help maintain compatibility with peptide-like architectures and allow incorporation into lysine-rich conjugates used for analytical labeling and molecular scaffold construction. Resulting bioconjugates and lysine-functional linkers can be further processed into multivalent constructs for downstream assay development, polymer conjugation, and controlled biomolecule modification.
4. Pharmaceutical Intermediate Preparation
L-Lysine monohydrate is relevant to pharmaceutical intermediate preparation and process chemistry intermediate design where amine-rich building blocks are required for synthesis of active pharmaceutical ingredient scaffolds and excipient-related components. The primary ε-amine provides a handle for forming protected amines, salts, and amide intermediates that can be carried through multi-step syntheses while maintaining stereochemical definition at the alpha carbon. Carboxyl functionality can be converted into activated forms for coupling, enabling incorporation of lysine-derived fragments into peptidic, peptidomimetic, or amide-linked structures. Industrially, lysine monohydrate can be managed as a practical feedstock for producing protected lysine derivatives and downstream chiral intermediates used in fine chemical manufacturing and chemical process development.
5. Polymer Modification
L-Lysine monohydrate is suitable for polymer modification and functional material synthesis where cationic or amine-reactive functionalities are incorporated into macromolecular systems. The ε-amine can be used to introduce reactive sites for crosslinking, grafting, or post-polymerization functionalization after conversion into protected or activated lysine-based derivatives. The amino acid's ability to form stable amide and carbamate linkages supports integration into biodegradable or bioinspired polymer backbones and surface coatings that require defined chemical reactivity. Lysine-derived functional polymers and coatings can be generated for industrial materials applications where controlled amine density and peptide-compatible chemistry are useful for subsequent coupling and surface engineering.
6. Analytical Research Standards
L-Lysine monohydrate serves as a reference material for analytical research involving amino acid quantification, derivatization method development, and calibration of analytical workflows. The presence of both alpha and side-chain amine groups enables standardized derivatization to detectable derivatives, supporting method validation in amino acid profiling and composition analysis. Lysine's defined L stereochemistry supports stereospecific analytical contexts where enantiomeric separation or chiral derivatization strategies are employed. Derived lysine standards and lysine-based internal references can also support monitoring of protected amino acid synthesis quality, peptide coupling outcomes, and side-chain functionalization consistency in synthetic and process chemistry settings.
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