H-alpha-Me-D-Phe(3-I)-OH is a non-natural, D-configured amino acid derivative featuring an α-methyl substitution on the amino acid backbone and a phenylalanine-derived aromatic side chain bearing an iodine substituent at the 3-position. The molecule contains a free amino group and a free carboxylic acid (-COOH) alongside the α-methyl group, with the side chain's iodinated aromatic ring providing a distinct halogenated handle for chemical characterization and structure-property studies. As a substituted amino acid with defined stereochemistry and a halogenated aromatic functionality, it is used as a building block in peptide and peptidomimetic synthesis and as a labeled or variant amino acid for analytical method development, molecular labeling strategies, and structure-activity or binding studies where steric and electronic effects of α-methylation and aromatic iodination are examined.
CAT No: CP25851
CAS No:457652-83-4
Synonyms/Alias:H-alpha-Me-D-Phe(3-I)-OH;457652-83-4;AmbotzHAA5330;SCHEMBL5182245;CTK8E9269;MolPort-008-268-014;RCYLCZQGMUWCBV-SNVBAGLBSA-N;3-Iodo-alpha-methyl-D-phenylalanine;ZINC38603506;(R)-alpha-Methyl-3-Iodophenylalanine;RT-013183;(R)-2-Amino-2-methyl-3-(3-iodophenyl)propanoicacid
Chemical Name:(R)-a-Methyl-3-iodophenylalanine (>98%, >98%ee)
H-alpha-Me-D-Phe(3-I)-OH is a chiral D-amino acid derivative of phenylalanine bearing an alpha-methyl substituent and a 3-iodo substituent on the aromatic ring. The molecule contains a free carboxylic acid and a sterically defined, alpha-disubstituted stereocenter, which can influence peptide bond formation and the conformational preferences of incorporated residues. The iodinated aromatic side chain provides a handle for halogen-based functionalization and a strong spectroscopic tag for analytical research, while the D-configuration supports stereochemical control in peptide and peptidomimetic synthesis. As an amino acid building block, it can function as a chiral intermediate for protected amino acid chemistry and downstream coupling into peptide-like structures.
1. Peptide Synthesis
H-alpha-Me-D-Phe(3-I)-OH is applied in peptide synthesis workflows where incorporation of D-configuration and an alpha-methylated backbone residue can tune steric and conformational properties of peptide chains. The free carboxylic acid and amino functionality (typically introduced via appropriate protection strategies when used as a coupling partner) enable standard peptide coupling chemistry, while the alpha-methyl group can affect amide bond formation kinetics and the dihedral-angle distribution of the resulting peptide. The 3-iodophenyl side chain is compatible with iterative synthesis by remaining stable under many coupling conditions and can later serve as a site for selective derivatization. Peptide building block preparation from this amino acid supports synthesis of D-amino acid-containing peptides and peptide analogs used in structural studies and method development in peptide chemistry.
2. Peptidomimetics And SAR Studies
H-alpha-Me-D-Phe(3-I)-OH is suitable for peptidomimetic construction and structure-activity relationship studies where aromatic halogenation and alpha-methyl substitution are used to modulate binding interactions and metabolic stability proxies. The iodinated phenyl ring can participate in halogen bonding patterns and provides a chemically addressable site for cross-coupling or electrophile-driven transformations when generating analog libraries. The D-stereochemistry and alpha-methyl substitution create a stereochemically constrained residue that can be incorporated into SAR panels to compare how backbone rigidity and side-chain electronics influence molecular recognition. Downstream derivatives prepared from this building block can support fragment-based molecular design and systematic variation of peptide-like scaffolds for biochemical screening campaigns.
3. Chiral Building Block Development
H-alpha-Me-D-Phe(3-I)-OH functions as a chiral amino acid intermediate for stereoselective synthesis routes that require an alpha-disubstituted D-amino acid motif. The defined stereocenter at the alpha position and the intact aromatic iodide allow downstream transformations that preserve stereochemical integrity while enabling controlled functional group interconversions. Protecting-group strategies can be applied to the amino and carboxyl groups to produce N-protected amino acid derivatives and activated coupling forms, supporting compatibility with solid-phase or solution-phase peptide assembly. The resulting chiral intermediates can be used to generate unnatural amino acid incorporation targets and to prepare stereochemically defined analogs for chemical biology research.
4. Side-Chain Functionalization
H-alpha-Me-D-Phe(3-I)-OH is used in synthetic organic chemistry as an iodinated aromatic amino acid platform for side-chain functionalization and diversified intermediate generation. The 3-iodo substituent can undergo palladium-catalyzed cross-coupling or other halogen-directed transformations to install aryl, heteroaryl, or functional substituents without altering the amino acid backbone. The alpha-methylated D-configuration helps maintain a consistent stereochemical environment during derivatization, which is important when producing libraries of amino acid derivatives for medicinal chemistry and biochemical probe development. Functionalized products derived from this building block can then be reintroduced into peptide-like frameworks or used as standalone chiral intermediates for further synthetic elaboration.
5. Analytical Standards And Labeling
H-alpha-Me-D-Phe(3-I)-OH is applicable to analytical research and method development where the iodinated aromatic side chain provides a strong mass-spectrometric and spectroscopic signature. The combination of D-configuration and alpha-methyl substitution supports unambiguous identification of stereochemically defined amino acid residues in complex mixtures, including peptide hydrolysates and enzymatic digestion products. The free carboxylic acid form can be used to prepare calibration materials or internal standards after appropriate derivatization to match the analytical method. The compound's structural features also make it a practical reference for validating stereochemical outcomes in protected amino acid synthesis and for tracking incorporation of iodinated aromatic residues in peptide construction studies.
6. Pharmaceutical Intermediate Preparation
H-alpha-Me-D-Phe(3-I)-OH is relevant to pharmaceutical manufacturing and process chemistry as a defined chiral amino acid intermediate for producing D-amino acid-containing building blocks used in peptide-based active ingredient synthesis. The presence of a free carboxylic acid and a stereochemically constrained alpha-methylated backbone enables conversion into protected amino acid derivatives and activated forms that are compatible with scalable peptide coupling strategies. The 3-iodophenyl functionality can serve as a late-stage diversification handle, allowing process routes to branch toward different analogs while maintaining a common stereochemical core. Industrially, this amino acid can support specialty chemical production of stereodefined intermediates for fine chemical synthesis and applied peptide chemistry, including the preparation of peptidomimetic scaffolds used in research-grade development pipelines.
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