(S)-α-Methyl-3-bromophenylalaine is a non-proteinogenic, aromatic amino acid derivative featuring an α-methyl substitution and a 3-bromophenyl side chain, classifying it as a substituted phenylalanine analogue used in peptide chemistry and chemical biology. The molecule contains both an amino group and a carboxyl functional group and bears the stereochemical descriptor (S) at the α-carbon, while the bromine substituent provides a halogenated handle that can support further derivatization or structure-property studies. As a substituted amino acid building block, it is employed in the preparation of modified peptides and analogues through standard amino acid coupling strategies, including incorporation into peptide sequences for conformational or reactivity investigations.
CAT No: CP27638
CAS No:1212117-73-1
Synonyms/Alias:(S)-Α-METHYL-3-BROMOPHENYLALANINE·H2O;α-Me-Phe(3-Br)-OH·H2O
Chemical Name:α-Me-Phe(3-Br)-OH·H2O
(S)-α-Methyl-3-bromophenylalaine is a chiral, non-proteinogenic amino acid building block featuring an α-methyl substituent and a 3-bromophenyl side chain, providing steric bias and a convenient aryl bromide handle for downstream functionalization. Its defined stereochemistry makes it useful in stereocontrolled medicinal chemistry and in the preparation of constrained amino acid derivatives for structure-activity relationship studies and peptidomimetic design. The brominated aromatic side chain supports coupling, cross-coupling, and late-stage diversification workflows, while the α-methyl group helps modulate conformational preferences in peptide-like scaffolds.
1. Peptidomimetic Building Block
(S)-α-Methyl-3-bromophenylalaine is used by medicinal chemistry and chemical biology groups to construct peptidomimetic and peptide-like scaffolds where backbone substitution is used to tune conformation and improve synthetic robustness during analog generation. The α-methyl stereocenter enables stereochemically defined incorporation into amide-linked structures, supporting SAR campaigns that compare side-chain and backbone effects across series. The 3-bromophenyl group further enables rapid derivatization into substituted aryl analogs, allowing chemists to explore electronic and steric contributions around the aromatic ring without redesigning the entire amino acid framework.
2. Diversified Aryl Bromide Intermediates
(S)-α-Methyl-3-bromophenylalaine serves as a practical intermediate for pharmaceutical intermediate development and specialty chemical manufacturing where an aryl bromide is required as a functional handle. Research teams employ it to access substituted phenyl derivatives through standard aryl bromide transformations, enabling generation of analog libraries for lead optimization. The combination of a chiral α-methyl center with a brominated aromatic side chain supports convergent synthesis strategies, allowing the amino acid fragment to be carried through multiple steps while retaining a defined stereochemical outcome for the final coupling partner.
3. Chiral Amino Acid Analog Synthesis
(S)-α-Methyl-3-bromophenylalaine is applied in stereocontrolled synthesis of non-natural amino acid analogs used for structure-property studies in peptide chemistry and protein-ligand interaction research. Laboratories that prepare constrained amino acid variants rely on the (S)-configuration to maintain consistent stereochemical identity across analog sets, which is important when comparing binding-relevant conformational effects in chemical biology probes or receptor-binding mimetics. The brominated phenyl side chain also supports iterative substitution patterns, making the compound a convenient starting point for producing closely related stereochemical series.
4. SAR Library Preparation
(S)-α-Methyl-3-bromophenylalaine is frequently selected for SAR library workflows that require a single, well-defined chiral amino acid precursor to generate multiple analogs with varied aromatic substitution. Medicinal chemistry teams use it to introduce a sterically biased aromatic amino acid motif into lead-like structures while keeping a modular diversification point at the aryl bromide. This approach streamlines parallel synthesis and purification planning for analog series, since the stereochemical element and the amino acid framework remain constant while the aromatic substitution pattern is varied to probe structure-activity relationships.
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