H-alpha-Me-D-Phe(3-Br)-OH is a D-configured, alpha-methylated phenylalanine derivative bearing a bromine substituent at the 3-position of the aromatic ring, classifying it as a non-natural amino acid suitable for peptide and chemical biology applications. The molecule contains a free carboxylic acid and an amino group on the alpha carbon, with the alpha-methyl substituent and the aryl bromine providing steric and electronic modulation of side-chain behavior relative to unmodified phenylalanine. As a halogenated, stereodefined building block, it is used in peptide synthesis and structure-activity or labeling studies where controlled incorporation of a brominated phenylalanine analogue supports downstream chemical handling and analytical characterization.
CAT No: CP25213
CAS No:1212321-90-8
Synonyms/Alias:AmbotzHAA5320;SCHEMBL6339840;MolPort-000-001-119;ZINC26897677;(R)-alpha-Methyl-3-bromophenylalanine;A60039;(R)-2-Amino-3-(3-bromophenyl)-2-methylpropionicacid;1212321-90-8
Chemical Name:(R)-a-Methyl-3-bromophenylalanine (>98%, >98%ee)
H-alpha-Me-D-Phe(3-Br)-OH is a chiral, D-configured phenylalanine derivative bearing an alpha-methyl substituent and a 3-bromo substituent on the aromatic ring. The molecule contains a free carboxylic acid and a sterically defined alpha-carbon that can influence amide formation, peptide coupling stereochemical outcomes, and conformational preferences in peptide-like scaffolds. The aromatic bromine provides a chemically addressable handle for cross-coupling, electrophilic aromatic substitution, and downstream derivatization without disturbing the amino acid backbone. As an amino acid building block and chiral synthetic intermediate, it can be incorporated into protected amino acid strategies or converted into activated derivatives for peptide construction and medicinal chemistry-style scaffold elaboration.
1. Peptide Synthesis
H-alpha-Me-D-Phe(3-Br)-OH is used in peptide building and peptide coupling research where a D-amino acid configuration and alpha-methyl substitution help tune backbone geometry and protease resistance profiles in peptidomimetic sequences. The free carboxylic acid and stereogenic alpha-carbon support conversion to activated esters or protected carboxyl derivatives, while the 3-bromo aromatic group remains compatible with standard peptide coupling conditions when orthogonal protection is selected appropriately. The aromatic bromide can be retained through peptide assembly and later used for late-stage functionalization of the resulting peptide analogs. Downstream, the compound enables synthesis of D-configured peptide fragments and analog libraries for structure-activity relationship studies and synthetic methodology development.
2. Peptidomimetics And SAR
H-alpha-Me-D-Phe(3-Br)-OH serves as a chiral residue for peptidomimetic construction in medicinal chemistry and SAR-focused molecular design, where the alpha-methyl group and D-configuration can modulate conformational bias and binding-site interactions. The phenyl ring bearing a 3-bromo substituent provides a handle for systematic aromatic substitution patterns, enabling controlled exploration of electronic and steric effects through cross-coupling or selective aromatic transformations. The amino acid backbone functionality supports incorporation into amide-rich scaffolds, allowing direct comparison between analogs differing only in aromatic substitution or alpha substitution. Resulting derivatives can be used to generate structure-activity relationship datasets and to support iterative scaffold refinement in applied chemical research.
3. Side-Chain Functionalization
H-alpha-Me-D-Phe(3-Br)-OH is applied in side-chain functionalization workflows where the aryl bromide acts as a reactive electrophile for coupling-based diversification while the alpha-methyl stereocenter preserves defined stereochemical identity. The carboxylic acid can be protected or converted to an amide/ester to prevent undesired participation during coupling steps, while the aromatic bromine enables installation of aryl, heteroaryl, or other substituents through standard synthetic organic chemistry routes. The resulting functionalized amino acid derivatives can then be carried forward into peptide coupling or used as standalone chiral fragments in fragment-based molecular design. This enables downstream generation of substituted D-phenylalanine analogs for chemical biology probes and synthetic intermediate preparation.
4. Protected Amino Acid Chemistry
H-alpha-Me-D-Phe(3-Br)-OH is suitable for protected amino acid synthesis strategies used to control chemoselectivity during peptide building block preparation. The presence of a free carboxylic acid supports formation of orthogonally protected carboxyl derivatives and N-protected forms, allowing selective activation for coupling while maintaining the D-stereochemical configuration at the alpha-carbon. The 3-bromo substituent can be maintained under many protection/deprotection regimes, enabling orthogonality between peptide synthesis steps and later aromatic diversification. The compound thus functions as a chiral intermediate for manufacturing-grade amino acid derivative routes and for generating peptide-compatible building blocks used in fine chemical synthesis.
5. Chemical Biology Probes
H-alpha-Me-D-Phe(3-Br)-OH is utilized in chemical biology research for constructing stereochemically defined amino acid probes and labeled peptide analogs where D-configuration and alpha-methyl substitution can influence stability and binding conformations. The free carboxylic acid and amino acid backbone enable attachment to carrier scaffolds or incorporation into peptide-like sequences that serve as recognition elements in biochemical assays. The aromatic bromine can be leveraged for post-assembly conjugation strategies, including coupling to fluorescent tags, affinity handles, or other modular groups, provided orthogonal protection is selected to preserve the backbone during conjugation. Downstream, the compound supports generation of probe libraries and mechanistic tools rooted in amino acid chemistry and peptide science.
6. Pharmaceutical Intermediate Preparation
H-alpha-Me-D-Phe(3-Br)-OH is relevant to pharmaceutical intermediate preparation and process chemistry intermediate design where a chiral, halogenated amino acid fragment can be converted into activated building blocks for downstream medicinal chemistry steps. The carboxylic acid functionality enables controlled transformation into coupling-ready forms, while the alpha-methyl stereocenter provides a defined chiral motif that can be carried through scale-up-oriented synthetic sequences. The 3-bromo aromatic group supports late-stage diversification, which can be integrated into manufacturing routes to access a range of substituted analogs without reconfiguring the core amino acid stereochemistry. This makes the compound applicable to specialty chemical production workflows that require chiral amino acid intermediates compatible with peptide coupling chemistry and iterative scaffold elaboration.
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