N-Me-Lys-OH is an amino acid derivative of lysine in which the ε-amino group is N-methylated, yielding a free α-amino group and a free carboxyl group while retaining the aliphatic (CH2)4 side-chain characteristic of lysine. The molecule contains an α-amino functionality and a carboxylic acid, and its N-methylated ε-amino side chain is less basic than an unmodified primary amine while still providing a nucleophilic site for salt formation and derivatization; the "Lys" designation indicates the lysine backbone stereochemical identity as written in the product name. N-Me-Lys-OH is used as a building block and reference substrate in peptide and amide synthesis where controlled modification of lysine's side-chain amine is required, including preparation of mono-methylated lysine residues for structure-activity studies and analytical method development.
N-Me-Lys-OH is an N-methylated lysine amino acid derivative that retains the canonical α-amino acid framework while presenting a stereodefined side chain bearing a terminal primary amine. The molecule contains an α-carboxylic acid and an N-methylated α-amino group, which together modulate basicity and peptide-coupling behavior relative to unmodified lysine. The chiral center at the α-position enables stereochemically controlled incorporation into peptide sequences and chiral intermediate design, while the ε-amine provides a reactive handle for selective derivatization, orthogonal protection, and further functional group installation. As an amino acid building block and biochemical research intermediate, N-Me-Lys-OH can participate in standard amide-forming chemistry and can be carried through protection, coupling, and deprotection strategies to generate N-methylated lysine-containing peptides and downstream functional derivatives.
1. Peptide Synthesis
N-Me-Lys-OH is applied in peptide building block preparation where N-methylation at the α-amino position influences amide formation and conformational preferences in lysine-containing sequences. The α-carboxylic acid and N-methylated α-amino functionality support peptide coupling chemistry after appropriate side-chain and carboxyl protection choices, enabling controlled incorporation of a stereodefined N-methyl lysine residue. The ε-primary amine can be protected orthogonally to withstand coupling conditions, then deprotected for subsequent elongation or for late-stage side-chain functionalization. Generated N-methyl lysine-containing peptides can serve as substrates for peptide mapping, backbone modification studies, and synthetic library construction in peptide chemistry workflows.
2. Chemical Biology
N-Me-Lys-OH is used for chemical biology studies targeting lysine-specific reactivity and amide-bond formation under controlled stereochemical and functional-group constraints. The ε-amine enables conjugation-compatible modifications such as carbamate or sulfonamide formation, while the N-methylated α-amino group can be leveraged to tune labeling reactivity and reduce susceptibility to certain enzymatic processing pathways that recognize canonical lysine motifs. The α-carboxylic acid allows conversion into activated derivatives for controlled immobilization or incorporation into peptide probes used to interrogate biomolecular interactions. Downstream products include N-methylated lysine analogs for receptor-binding assays, protease substrate panels, and chemically defined probes used in biomolecular recognition experiments.
3. Side-Chain Functionalization
N-Me-Lys-OH is suitable for side-chain functionalization strategies that exploit the terminal ε-amine as a site-selective handle for installing linkers, affinity tags, or reactive groups. The presence of an N-methylated α-amino group can improve stability of the amino acid derivative during multi-step synthesis, while the stereogenic α-center supports consistent stereochemical outcomes in downstream derivatives. ε-amine derivatization can proceed through protection and selective deprotection sequences, enabling formation of amide, urea, sulfonamide, or alkylated products that retain the α-carboxyl functionality for further coupling. Resulting functionalized lysine derivatives can be employed as intermediates for conjugate synthesis, scaffold diversification, and fine chemical production routes that require a defined lysine stereochemistry.
4. Protected Amino Acids
N-Me-Lys-OH is relevant to protected amino acid chemistry where N-methylation changes protecting-group selection and deprotection behavior for peptide-grade intermediates. The α-carboxylic acid can be converted to ester or activated acid forms, while the N-methylated α-amino group can be maintained or temporarily transformed depending on the coupling strategy used to assemble N-methylated peptide bonds. The ε-amine typically requires side-chain protection to prevent undesired branching or crosslinking during amide coupling, enabling orthogonal control over sequential functional group exposure. Prepared protected derivatives can serve as chiral building blocks for N-methyl lysine incorporation in peptide synthesis, combinatorial chemistry, and stereochemically controlled intermediate manufacturing.
5. Process Chemistry Intermediate
N-Me-Lys-OH is applicable as a chiral amino acid intermediate in process chemistry and specialty chemical production where a single stereodefined lysine framework with an N-methylated α-amino group supports robust downstream conversion. The combination of an α-carboxylic acid and a primary ε-amine allows conversion into activated intermediates, salt forms, or protected derivatives that can be processed through standard industrial peptide and conjugate manufacturing steps. The N-methyl substituent can influence chemoselectivity during protection, activation, and coupling operations, supporting reproducible formation of N-methylated amide linkages in controlled synthetic sequences. Downstream utility includes preparation of N-methyl lysine-containing fragments, peptidomimetic precursors, and chemically defined intermediates used in industrial fine chemical synthesis and applied biochemical reagent production.
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