D-2-Methylserine is a D-configured, non-proteinogenic amino acid belonging to the serine family, featuring a side chain derived from serine with a methyl substituent at the alpha position (2-methyl substitution). The molecule contains a free amino group and a carboxyl group and bears a hydroxyl-containing side chain that is substituted by the additional methyl group, which changes steric and hydrogen-bonding properties relative to unmodified serine. In peptide chemistry and chemical biology, D-2-Methylserine is used as a defined amino acid building block for structure-activity studies, stereochemical probing, and the preparation of modified peptides and amino acid derivatives where altered side-chain geometry and polarity are required.
CAT No: CP08403
D-2-Methylserine is a chiral amino acid derivative of serine in which the alpha carbon bears a methyl substituent, giving a stereodefined D-configuration and a sterically biased side chain. The molecule contains a primary amino functionality and a carboxylic acid, enabling formation of zwitterionic species and participation in standard peptide coupling chemistry after appropriate activation. The side-chain hydroxyl group supports hydrogen-bonding and can be selectively protected or converted to reactive intermediates for side-chain functionalization. The presence of the additional methyl stereocenter makes D-2-methylserine a useful chiral building block for constructing constrained amino acid motifs and for probing how steric effects influence peptide conformations and downstream reactivity.
1. Peptide Synthesis
D-2-Methylserine is used in peptide building block preparation where the amino acid backbone can be incorporated into peptide coupling workflows using standard N-protection and carboxyl activation strategies. The side-chain hydroxyl group can be protected to prevent competing reactions during amide bond formation, while the D-stereochemistry is retained through orthogonal protection and activation sequences. Incorporation of the alpha-methyl substituent can bias local backbone geometry and influence dihedral preferences, which is relevant for constructing peptides with altered stability or recognition properties. D-2-methylserine-containing peptides can serve as research-grade analogs for mapping how steric modulation at the alpha position affects peptide assembly, folding tendencies, and chemical robustness.
2. Amino Acid Derivatization
D-2-Methylserine is suitable for amino acid derivatization programs that target the side-chain hydroxyl for conversion into protected intermediates, leaving groups, or functional handles for subsequent coupling. The hydroxyl group can be transformed into ether or ester derivatives, enabling controlled reactivity during multistep synthesis and supporting orthogonal deprotection for sequential functionalization. The amino and carboxyl groups can be temporarily masked to generate reactive species for downstream formation of amides, esters, or carbamates, supporting the synthesis of libraries of D-2-methylserine analogs. Side-chain-modified D-2-methylserine derivatives can then be used as intermediates for peptidomimetic construction, stereodefined scaffold diversification, and process-friendly route development in fine chemical synthesis.
3. Chemical Biology Probes
D-2-Methylserine is applied in chemical biology research as a stereodefined amino acid analog for studying structure-function relationships in peptide-mediated recognition systems. The D-configuration and alpha-methyl substitution provide a handle for evaluating how constrained sterics affect hydrogen-bonding patterns involving the side-chain hydroxyl and the backbone amide network. The hydroxyl-bearing side chain can be functionalized to introduce clickable tags or affinity handles, enabling incorporation into probes that track peptide binding, localization, or interaction kinetics in biochemical assays. Downstream labeling reagents and probe scaffolds derived from D-2-methylserine can support analytical and mechanistic studies where stereochemical fidelity is required for meaningful molecular recognition.
4. Peptidomimetics And SAR
D-2-Methylserine is relevant to peptidomimetic construction and structure-activity relationship studies where alpha-methylation is used to modulate conformational preferences and metabolic stability proxies. The amino acid's protected or activated carboxyl and N-functional groups enable systematic replacement of native serine residues in peptide analogs while maintaining a comparable functional group array. The side-chain hydroxyl supports retention of serine-like hydrogen-bonding motifs, while the methyl substituent can tune steric bulk and influence local secondary structure propensity. D-2-methylserine-containing analogs can be employed to generate stereochemically defined SAR series for fragment-based molecular design and iterative scaffold optimization in research-grade discovery workflows.
5. Pharmaceutical Intermediate Preparation
D-2-Methylserine is used as a chiral intermediate in pharmaceutical intermediate preparation where stereodefined amino acid fragments are required for assembling protected building blocks. The molecule's amino acid functionality supports conversion into N-protected derivatives and activated carboxyl equivalents that can be carried forward into peptide-like or peptidomimetic syntheses. The hydroxyl group can be selectively protected to align with orthogonal deprotection schemes, supporting controlled manufacturing sequences that minimize side reactions and enable stepwise functional group unveiling. D-2-methylserine-derived intermediates can therefore serve in process chemistry routes for producing stereodefined chiral fragments used in specialty chemical production and downstream active-molecule synthesis planning.
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