2-Methy-D-Phenylalanine is a non-proteinogenic, stereochemically specified amino acid derivative featuring a D-configured α-amino acid backbone with a benzyl side chain bearing an additional methyl substituent at the ortho position. The molecule contains a free amino group and a carboxyl group and presents an aromatic side chain with increased steric bulk and altered hydrophobicity relative to unsubstituted phenylalanine, which can influence conformational preferences when incorporated into peptide structures. In chemical biology and peptide chemistry, it is used as a substituted phenylalanine analogue for structure-activity studies, side-chain effect investigations, and the preparation of modified peptides or peptidomimetics where the methylated aromatic ring provides a defined chemical handle for binding and physicochemical property comparisons.
CAT No: CP15602
CAS No:80126-54-1
Synonyms/Alias:D-2-Methylphenylalanine;80126-54-1;(R)-2-Amino-3-(o-tolyl)propanoicacid;D-2-METHYLPHE;(2R)-2-amino-3-(2-methylphenyl)propanoicacid;2-Methyl-D-phenylalanine;O-METHYL-D-PHENYLALANINE;AC1OCVVJ;2-Methy-D-Phenylalanine;H-O-ME-D-PHE-OH;D-2-ME-PHE-OH;D-PHE(2-ME)-OH;SCHEMBL383453;H-D-PHE(2-ME)-OH;CTK8F0537;MolPort-001-758-741;ZINC406142;AB10076;AC-5867;AM83410;OR14699;AJ-22466;AK109372;KB-25069;AB0048242
2-Methy-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing an additional methyl substituent on the alpha-carbon, which makes it a useful stereodefined building block for peptidomimetic and structure-activity relationship studies. Its non-natural stereochemistry and steric/electronic modification relative to phenylalanine support incorporation into synthetic peptide frameworks where researchers want to probe conformational effects and backbone substitution patterns. In medicinal chemistry and chemical biology workflows, this amino acid analog is typically handled as a defined chiral intermediate for downstream coupling into modified peptides and peptidomimetics.
1. Peptidomimetic Building Block
2-Methy-D-Phenylalanine is used by medicinal chemistry and peptide chemistry teams to construct peptidomimetic scaffolds that incorporate a stereochemically constrained, non-natural residue. The alpha-methyl substitution changes steric bulk and backbone geometry compared with standard phenylalanine, which is valuable when developing analog series for SAR (structure-activity relationship) work or for tuning properties such as conformational preference in synthetic peptide-like molecules. Researchers commonly employ it during custom peptide synthesis workflows to generate modified sequences for screening, comparison to parent phenylalanine-containing analogs, and iterative optimization of residue-level structure features.
2. Stereodefined SAR Analogues
2-Methy-D-Phenylalanine supports structure-activity relationship studies where stereochemistry is treated as a key design variable rather than a fixed assumption. Because the compound is the D-enantiomer and includes the additional methyl substituent, it is frequently selected to create residue-level stereochemical "controls" that help distinguish the impact of side-chain identity versus backbone substitution. Chemical biology groups and medicinal chemistry process development teams use these analogues to build systematic libraries of modified peptides or peptidomimetics, enabling clearer interpretation of how alpha-methylation and D-configuration influence the behavior of the overall scaffold in downstream assay systems.
3. Chiral Intermediate Development
2-Methy-D-Phenylalanine is also used as a chiral amino acid intermediate for downstream synthesis of non-natural amino acid derivatives and specialized coupling partners. Organic synthesis teams and pharmaceutical intermediate developers rely on defined stereochemical building blocks to prepare further functionalized analogs used in peptide coupling strategies, fragment assembly, and scaffold diversification. In practice, the compound's non-proteinogenic nature and stereochemical identity make it a practical starting point when the goal is to maintain stereochemical fidelity through subsequent derivatization steps that feed into modified peptide or peptidomimetic production.
4. Modified Peptide Library Synthesis
2-Methy-D-Phenylalanine is commonly incorporated into modified peptide libraries prepared for research-scale screening and mechanistic studies in chemical biology. By introducing a non-natural D-residue with alpha-methyl substitution, library designers can systematically vary residue composition while maintaining a consistent backbone substitution motif across analogs. This approach is particularly useful when researchers want to compare multiple sequence contexts that include the same stereodefined building block, supporting downstream evaluation of how backbone substitution patterns affect the properties of peptide-like constructs used for binding studies, target engagement experiments, or assay development.
3. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
4. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes
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