H-alpha-Me-D-Phe(3-NO2)-OH is a D-configured, alpha-methylated phenylalanine derivative bearing a meta-nitro substituent on the aromatic ring, classifying it as a non-natural amino acid suitable for peptide and chemical biology studies. The molecule contains a free carboxylic acid and a secondary amino acid center (alpha-methyl substitution) with an aromatic side chain bearing a nitro group, which provides an electron-withdrawing functional handle while maintaining the basic amino acid framework. As a substituted amino acid building block, it is used in synthetic peptide workflows and structure-activity or labeling studies where incorporation of an alpha-methyl residue and an aryl nitro functionality is used to probe conformational effects, stability, and side-chain electronic properties.
CAT No: CP25215
CAS No:1215092-13-9
Chemical Name:(R)-a-Methyl-3-nitrophenylalanine (>98%, >98%ee)
H-alpha-Me-D-Phe(3-NO2)-OH is a chiral, D-configured phenylalanine derivative bearing an alpha-methyl substituent (H-alpha-Me) and a meta nitro group on the aromatic ring (3-NO2). The molecule contains the amino acid core with a free carboxylic acid and a stereogenic center at the alpha carbon, while the aromatic nitro substituent introduces strong electron-withdrawing character and distinctive reactivity for downstream functionalization. The alpha-methyl substitution can influence peptide coupling geometry and conformational preferences relative to standard phenylalanine, supporting its use as a stereochemically defined building block. The combination of a D-amino acid framework, an unprotected acid functionality, and an aryl nitro group makes the compound a practical chiral intermediate for protected amino acid synthesis, peptide construction, and aromatic derivatization routes.
1. Peptide Synthesis
H-alpha-Me-D-Phe(3-NO2)-OH is applied in peptide building block preparation and solid-phase or solution-phase peptide synthesis where a D-amino acid residue is required for stereochemical control. The free carboxylic acid and amino functionality enable conversion to an N-protected amino acid derivative, supporting peptide coupling chemistry after appropriate protection of the amine and, when needed, temporary protection or activation strategies for the acid. The alpha-methyl stereocenter can modulate backbone sterics and can be incorporated into peptides to tune local conformation and resistance to proteolysis, while the 3-nitro aromatic group can survive many peptide assembly conditions and serve as a handle for later transformations. Incorporation of this residue supports construction of D-Phe-containing analogs and peptidomimetic scaffolds for structure-activity relationship studies and peptide chemistry research.
2. Chiral Amino Acid Intermediate
H-alpha-Me-D-Phe(3-NO2)-OH is suitable as a chiral amino acid intermediate for manufacturing routes that require a defined D-configuration and an alpha-methylated stereocenter. The stereogenic alpha carbon and the aromatic nitro group provide chemically addressable features for stepwise derivatization, including preparation of N-protected forms (e.g., carbamate or sulfonamide strategies) and conversion to activated ester or coupling-ready derivatives for downstream syntheses. The electron-withdrawing nitro substituent can be used to control reactivity during aromatic functional group interconversions, including selective reduction or nucleophilic aromatic substitution after appropriate activation. Downstream use commonly includes preparation of chiral intermediates for peptidomimetics, chiral ligands, and fine chemical synthesis where stereochemical integrity and functional group compatibility are required.
3. Side-Chain Functionalization
H-alpha-Me-D-Phe(3-NO2)-OH is employed in aromatic functionalization workflows where the meta nitro group functions as a controllable functional handle on a phenylalanine side chain. The nitro substituent can be transformed into an aniline, heteroaryl, or other nitrogen-containing motifs under reduction or subsequent derivatization conditions, enabling generation of analog libraries for chemical biology and SAR studies. The alpha-methyl D-amino acid framework can remain intact during side-chain modification, allowing the resulting products to be carried forward into peptide coupling or conjugation steps. The presence of the amino acid backbone supports conversion into protected derivatives for sequential synthesis, ultimately enabling access to nitro-derived aromatic variants used in molecular design and target-focused intermediate preparation.
4. Bioconjugation Chemistry
H-alpha-Me-D-Phe(3-NO2)-OH can be used in bioconjugation and chemical biology workflows that require incorporation of a D-amino acid motif into protein-binding peptides or labeling constructs. The amino acid core supports conversion into N-protected, coupling-ready derivatives for attachment to biomolecule-reactive scaffolds, while the carboxylic acid functionality enables formation of amide linkages or ester-linked intermediates after activation. The aromatic nitro group can serve as a chemical handle for later modification, including conversion to more conjugation-friendly aromatic functionalities that can participate in coupling chemistries compatible with biomolecule labeling strategies. D-configuration and alpha-methyl substitution can help maintain stereochemical stability and influence local binding conformations in conjugates used for mechanistic studies and biomolecule modification.
5. Pharmaceutical Intermediate Preparation
H-alpha-Me-D-Phe(3-NO2)-OH is relevant to pharmaceutical intermediate preparation where stereodefined, nitro-functionalized amino acid derivatives are needed for peptidomimetic and peptide-like active ingredient synthesis. The protected amino acid chemistry compatibility of the D-amino acid scaffold supports conversion into N-protected intermediates that can be coupled into larger fragments under manufacturing-relevant conditions, while the aromatic nitro group provides a functional group that can be carried through multi-step sequences and later transformed into structures used in medicinal chemistry. The alpha-methyl stereocenter can be leveraged to access conformationally constrained analogs and to generate building blocks for fragment assembly and SAR-driven molecular diversification. Industrially, this compound can function as a process chemistry intermediate for controlled stereochemical introduction of D-amino acid residues into drug-like scaffolds and related fine chemical production.
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