N-α-benzyl-D-methionine methylester hydrochloride is a D-configured methionine derivative in which the amino acid backbone is present as a methyl ester and the α-amino group is N-benzylated, classifying it as an amino acid methyl ester hydrochloride salt. The molecule contains a carboxylate ester functionality (methyl ester), an N-benzyl-protected amino group, and a thioether side chain characteristic of methionine, with the hydrochloride counterion associated to the basic nitrogen to form the salt. In peptide and amino acid chemistry, this protected, esterified form can serve as a substrate or building block for preparing more complex methionine-containing derivatives, including labeled or functionalized analogues, where controlled chemoselectivity and ester handling are relevant to stepwise synthesis and analytical characterization.
CAT No: CP01508
N-α-benzyl-D-methionine methylester hydrochloride is a D-configured methionine methyl ester bearing an N-α benzyl substituent, with the hydrochloride salt form enhancing handling of the amino functionality. The molecule contains a thioether side chain characteristic of methionine, a chiral center at the α-carbon, and an ester carbonyl that participates in downstream transformations toward protected amino acid derivatives. The benzylated nitrogen can be maintained under peptide-coupling conditions and removed by hydrogenolysis or related deprotection strategies when switching from ester/amide assembly to free amino acid or alternative protection schemes. The combination of stereodefined D-configuration, N-substitution, and ester functionality makes the compound a chiral amino acid intermediate suited to controlled peptide building block preparation and sulfur-functional derivatization routes.
1. Peptide Synthesis
N-α-benzyl-D-methionine methylester hydrochloride supports peptide coupling workflows in synthetic peptide chemistry where a D-methionine residue is required for stereochemical control or for producing D-enriched peptide analogs. The methyl ester carbonyl and the benzyl-protected amine provide defined reactive handles for conversion into activated carboxyl equivalents and subsequent amide bond formation. The thioether side chain can be preserved during coupling or selectively modified after assembly to generate methionine analogs with altered oxidation state or nucleophilicity. Downstream, the stereodefined residue can be incorporated into peptide fragments for library synthesis, sequence optimization, and mechanistic studies of peptide stability.
2. Chiral Amino Acid Intermediate
N-α-benzyl-D-methionine methylester hydrochloride functions as a chiral amino acid intermediate for enantiospecific synthesis of D-methionine-containing scaffolds. The D-configuration at the α-carbon, together with the N-α benzyl group, enables predictable stereochemical outcomes when the ester is transformed into amides or when the nitrogen is carried through protection/deprotection sequences. The hydrochloride salt form can facilitate consistent handling during derivatization steps that require controlled amino availability without premature side reactions. The resulting intermediates can be used to prepare protected amino acids, peptide building blocks, or chiral fragments for stereochemical SAR studies and stereocontrolled fine chemical synthesis.
3. Side-Chain Functionalization
N-α-benzyl-D-methionine methylester hydrochloride is suitable for sulfur chemistry applications that exploit the methionine thioether as a functional handle for post-assembly modification. The thioether can potentially be oxidized to sulfoxide or further transformed under controlled conditions to tune polarity, hydrogen-bonding behavior, and reactivity of the side chain in peptide or small-molecule contexts. The ester and N-benzyl features allow the compound to be carried through multi-step sequences while maintaining a defined backbone for later conversion into amide-linked derivatives. Downstream products include sulfur-modified amino acid derivatives and peptidomimetic building blocks used to probe structure-function relationships and to generate analogs with altered physicochemical properties.
4. Peptidomimetics And SAR Studies
N-α-benzyl-D-methionine methylester hydrochloride can be applied in peptidomimetic construction where D-amino acid incorporation is used to modulate conformational preferences and proteolytic resistance in bioactive-like scaffolds. The N-α benzyl protection strategy and the methyl ester provide a controlled platform for converting the residue into amide or other linkage types that mimic peptide bonds while maintaining stereochemical identity. The methionine thioether side chain can be used as a recognizable motif for analog series generation, including sulfur-oxidation state variants that affect molecular recognition patterns. The resulting D-methionine-containing analogs can be used for SAR studies, fragment elaboration, and structure-guided optimization in applied medicinal chemistry research.
5. Pharmaceutical Intermediate Preparation
N-α-benzyl-D-methionine methylester hydrochloride serves as a process-relevant intermediate for manufacturing routes that require stereodefined D-methionine derivatives for downstream synthesis of peptide-like or amino acid-derived intermediates. The salt form and the N-α benzyl protection can support robust handling and consistent conversion into carboxyl-activated derivatives or amide-linked intermediates during scale-up-oriented synthetic planning. The methyl ester functionality provides a handle for controlled transformations into acids, amides, or other activated carboxyl derivatives used in subsequent synthetic steps. Downstream utility includes preparation of protected amino acid building blocks, D-amino acid fragments, and sulfur-functional intermediates that feed into specialty chemical production and pharmaceutical intermediate supply chains.
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