Bzl-L-Met-OMe*HCl

Bzl-L-Met-OMe*HCl is the hydrochloride salt of the methyl ester of L-methionine protected at the amino group with a benzyl (Bzl) carbamate/benzyl-type protecting strategy, giving a chiral amino acid ester bearing a thioether side chain characteristic of methionine. The molecule combines an L-configured stereocenter with a carboxylate functionality masked as a methyl ester, while the benzyl-protected nitrogen supports controlled peptide coupling after appropriate activation or deprotection. The thioether (-S-CH3) can participate in oxidation-state-dependent transformations and can be leveraged for orthogonal side-chain derivatization without disturbing the backbone stereochemistry. As an amino acid ester hydrochloride, the salt form improves handling and can support downstream synthetic sequences that require stable chiral intermediates for peptide building block preparation and fine chemical synthesis.

1. Peptide Synthesis

Bzl-L-Met-OMe*HCl is used in peptide building block preparation where the L-methionine backbone and benzyl-protected amino functionality support controlled peptide coupling chemistry. The methyl ester can be selectively manipulated for C-terminal derivatization strategies, while the benzyl-protected amine enables amide bond formation after conversion to an activated derivative or after orthogonal deprotection steps. The thioether side chain remains compatible with many peptide synthesis conditions and can be carried through as a protected functional handle for later oxidation or substitution. The resulting peptide analogs and protected intermediates can be used to construct methionine-containing sequences for biochemical research and synthetic methodology development.

2. Side-Chain Functionalization

Bzl-L-Met-OMe*HCl is applicable to side-chain functionalization workflows that exploit the methionine thioether as a chemically addressable motif. The sulfur-containing side chain can be transformed into sulfoxide or sulfone analogs under controlled conditions, enabling stereochemically informative sulfur oxidation states for structure-activity relationship studies and conformational probing in peptidomimetics. The preserved L-configuration and protected backbone reduce the risk of racemization during derivatization, supporting preparation of sulfur-modified amino acid derivatives for downstream conjugation or analytical standards. The methyl ester and N-protection strategy also allow staged functional group interconversions that feed into larger fragment assembly and functional molecule generation.

3. Chiral Amino Acid Intermediate

Bzl-L-Met-OMe*HCl serves as a chiral amino acid intermediate for stereoselective synthesis where the L-methionine stereocenter is retained through protected-amino and ester-masked functional groups. The benzyl-protected amine and methyl ester provide a protected scaffold that can be converted into activated coupling partners, enabling incorporation into peptide fragments or chiral auxiliaries depending on the synthetic route design. The hydrochloride salt form can facilitate reproducible handling in process chemistry intermediate preparation, particularly when subsequent steps require consistent solubility and controlled deprotection. Downstream, the compound can be employed to manufacture methionine-containing intermediates for fine chemical synthesis and specialty chemical production that depend on chiral amino acid building blocks.

4. Bioconjugation Chemistry

Bzl-L-Met-OMe*HCl can be applied to bioconjugation chemistry as a methionine-based handle for constructing conjugatable peptide fragments and sulfur-modified linkers. The thioether side chain provides a platform for generating oxidation-state variants that can participate in selective labeling strategies and enable controlled attachment points in biomolecule modification schemes. The protected amino group and ester functionality support stepwise conversion into amide-containing conjugation-ready fragments, including C-terminally functionalized derivatives suitable for coupling to carriers or biomolecular scaffolds. The resulting conjugation intermediates can be used in chemical biology workflows that require defined amino acid stereochemistry and functional group positioning for probing molecular recognition and labeling behavior.

5. Pharmaceutical Manufacturing Intermediates

Bzl-L-Met-OMe*HCl is suitable for pharmaceutical manufacturing intermediate preparation where protected amino acid esters and N-protected methionine derivatives are used to assemble peptide-like building blocks under industrially scalable synthetic conditions. The benzyl-protected nitrogen and methyl ester form a protected backbone that can be routed through activation, coupling, and controlled deprotection sequences to yield methionine-containing intermediates for drug discovery chemistry and process development. The thioether side chain can be carried through as a stable functionality during manufacturing steps and can be converted to oxidized sulfur variants when specific physicochemical properties or analytical targets require it. The compound thus functions as a chiral, structurally defined amino acid derivative that supports downstream synthetic route design for peptide and peptidomimetic manufacturing workflows.

1. Store-operated Ca2+ entry sustains the fertilization Ca2+ signal in pig eggs

2. Urinary Metabolites Associated with Blood Pressure on a Low-or High-Sodium Die

3. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis

4. Immune responses to peptides containing homocitrulline or citrulline in the DR4-transgenic mouse model of rheumatoid arthritis

5. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)