N-α-benzyl-L-methionine methylester hydrochloride is a protected methionine derivative in which the amino acid backbone bears an N-α benzyl substituent and a methyl ester at the carboxyl terminus, with the methionine thioether side chain preserved. The molecule contains a benzyl-protected amino group (as an N-α benzyl substituent) and a methyl ester functional group, while the hydrochloride counterion is associated with the basic nitrogen to form a salt form suitable for handling. This amino acid ester and N-substituted derivative is used as a chemically defined building block for peptide and amino acid derivative synthesis, including preparation of methionine-containing sequences and side-chain-tolerant analog studies where the thioether functionality and ester/amine protection pattern control chemoselectivity during coupling steps.
CAT No: CP01509
N-α-benzyl-L-methionine methylester hydrochloride is an L-methionine derivative in which the α-amino group is benzylated and the α-carboxyl group is converted to a methyl ester, with the overall salt form provided as the hydrochloride to support handling of the protected amine. The molecule retains the thioether side chain characteristic of methionine, enabling sulfur-centered reactivity under appropriate conditions while remaining compatible with many peptide-coupling workflows when the ester and amine protection are managed correctly. The stereogenic center at the α-position is fixed in the L-configuration, which is relevant for stereospecific peptide bond formation and for constructing chiral peptide analogs. The combination of N-α benzyl protection and C-terminal methyl ester functionality makes the compound a chiral amino acid intermediate suited to downstream transformations such as ester activation, amide formation, and controlled deprotection strategies.
1. Peptide Synthesis
N-α-benzyl-L-methionine methylester hydrochloride is used in peptide coupling research and peptide building-block preparation where a protected methionine residue is required. The benzyl-protected α-amine and methyl ester C-terminus provide functional-group handles that can be converted into an acyl donor or an amide-forming partner depending on the activation and deprotection sequence. The L-stereocenter supports stereodefined incorporation into oligopeptides and peptidomimetics, while the thioether side chain can be preserved through coupling steps and later used for selective oxidation or derivatization. Downstream processing can generate protected methionine-containing peptide fragments and can feed synthesis of longer sequences used in biochemical research and materials-oriented peptide studies.
2. Side-Chain Functionalization
N-α-benzyl-L-methionine methylester hydrochloride serves as a sulfur-functional amino acid intermediate for side-chain modification strategies in chemical biology and synthetic organic chemistry. The methionine thioether is positioned as a reactive handle that can undergo controlled oxidation to sulfoxide or sulfone analogs, enabling redox-sensitive probes, conformational tuning, or altered polarity in peptide scaffolds. The benzyl-protected α-amine and methyl ester allow selective functionalization planning, since side-chain transformations can be performed while maintaining the protected backbone for subsequent coupling or conversion to a carboxylate equivalent. Resulting derivatives can be carried into peptide analog construction, SAR studies on sulfur oxidation state effects, and downstream preparation of labeled or functionalized biomolecule fragments.
3. Chiral Amino Acid Intermediate
N-α-benzyl-L-methionine methylester hydrochloride is applied as a chiral amino acid intermediate for stereoselective synthesis routes that require an L-configured methionine unit with orthogonal functional-group protection. The hydrochloride salt form stabilizes the benzyl-protected amine for handling, while the methyl ester provides a controllable C-terminal functionality for conversion to activated esters, acid derivatives, or amide-forming intermediates. The fixed α-stereochemistry supports predictable outcomes in fragment assembly and in the construction of dipeptide and tripeptide building blocks where stereochemical integrity is required. The compound can be employed in fine chemical synthesis planning and in process chemistry intermediate preparation for methionine-containing chiral libraries.
4. Pharmaceutical Intermediate Preparation
N-α-benzyl-L-methionine methylester hydrochloride is suitable for industrially relevant intermediate synthesis where protected amino acid derivatives are required for manufacturing-scale peptide-like or peptidomimetic scaffolds. The N-α benzyl protection and methyl ester functionality align with common protection/deprotection and activation logic used to convert amino acid derivatives into acylating agents or coupling-ready fragments. The thioether side chain can be carried through early manufacturing steps and then transformed into oxidation-state variants when the synthetic route calls for altered physicochemical properties in downstream intermediates. The resulting methionine-based intermediates can be routed into specialty chemical production workflows that generate protected peptide segments, SAR-focused analogs, and other chiral building blocks used in applied chemical development.
5. Bioconjugation Chemistry
N-α-benzyl-L-methionine methylester hydrochloride can be used in bioconjugation-oriented synthesis where methionine-derived thioether functionality is leveraged for constructing conjugatable molecular handles. The protected α-amine and ester form enable controlled generation of methionine-containing fragments that can be incorporated into peptide linkers prior to conjugation to biomolecular targets such as proteins or nucleic-acid-associated scaffolds. The sulfur side chain may serve as a site for oxidative activation or for introducing polarity and reactivity changes that improve conjugation chemistry compatibility in linker designs. Downstream use includes preparation of methionine-containing peptide linkers and conjugation-ready intermediates for chemical biology workflows and analytical reagent development.
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