H-D-Phg-OEt · HCl is a D-configured phenylglycine amino acid ester hydrochloride, where the amino acid side chain is a benzyl-substituted aromatic (phenylglycine) and the carboxyl group is esterified as an ethyl ester. The molecule contains a free amino functionality in the form of an amino hydrochloride salt, with the ester carbonyl as the primary carboxyl-derived functional group and the aromatic ring providing hydrophobic and π-interaction character relevant to peptide and ligand design. As an amino acid ester salt, it is commonly used as a protected/derivatized building block for peptide synthesis and for preparing further amino acid derivatives, including labeled or conjugatable phenylglycine-containing intermediates in chemical biology and structure-activity studies.
CAT No: CP26531
CAS No:17609-48-2
Synonyms/Alias:(R)-Ethyl2-amino-2-phenylacetatehydrochloride;17609-48-2;(R)-Ethyl2-amino-2-phenylacetateHCl;D-(-)-Alpha-PhenylglycineEthylEsterHydrochloride;DL-Phenylglycineethylesterhydrochloride;PubChem10931;MolPort-006-122-287;ACT07378;AKOS008145379;AKOS015933062;MCULE-2364231684;PS-7935;AK-63329;AM018326;SC-16354;FT-0624335;ST24035543;ETHYL(2R)-2-AMINO-2-PHENYLACETATEHYDROCHLORIDE
H-D-Phg-OEt · HCl is a protected amino acid derivative corresponding to D-phenylglycine ethyl ester hydrochloride, featuring a chiral α-carbon and a benzyl-like side chain that can participate in hydrophobic and aromatic recognition. The ethyl ester and the hydrochloride salt form a defined C-terminal functional handle while the amino functionality is present as an amine hydrochloride, enabling controlled reactivity during protected amino acid synthesis and subsequent coupling steps. The stereochemical configuration at the D-α-center supports stereodefined incorporation into peptide-like scaffolds and chiral building block sequences. The aromatic side chain and ester group together make the compound suitable for downstream transformations into amide-linked products, ester-to-acid/amide conversion pathways, and stereochemically consistent intermediate preparation.
1. Protected Amino Acid Synthesis
H-D-Phg-OEt · HCl is used in protected amino acid chemistry as a chiral amino acid ester salt precursor for stepwise peptide building block preparation. The D-phenylglycine framework provides a stereodefined α-amino center and an aromatic side chain, while the ethyl ester offers a protected C-terminal functionality that can be carried through coupling chemistry and later converted for further elaboration. Hydrochloride salt formation helps manage amine protonation state during derivatization, supporting compatibility with standard peptide coupling workflows after appropriate neutralization and N-protection strategies. Downstream processing can generate amide-linked intermediates and stereochemically defined peptide fragments used in synthetic methodology development and fine chemical synthesis planning.
2. Peptide Coupling Chemistry
H-D-Phg-OEt · HCl is applied in peptide synthesis workflows where a D-configured phenylglycine residue is required for conformational control and side-chain-directed interactions. The amino ester structure supports conversion into an activated coupling partner after appropriate protection of the amine and handling of the ester group to enable formation of peptide bonds at the α-position. The aromatic side chain can influence solubility and aggregation behavior of the growing peptide, which is relevant when constructing stereodefined sequences for analytical standards and peptidomimetic scaffolds. Incorporation of the D-phenylglycine unit can also facilitate access to peptide analogs that retain defined stereochemistry for subsequent SAR studies and fragment-based molecular design.
3. Peptidomimetic And SAR Studies
H-D-Phg-OEt · HCl is suitable for peptidomimetic construction and structure-activity relationship investigations that require a chiral aromatic amino acid element. The D-configuration at the α-carbon enables stereospecific placement of the phenylglycine moiety into peptide-like backbones, supporting the generation of analog series with controlled stereochemical variation. The ester functionality can serve as a synthetic handle for conversion to carboxylic acid derivatives or for preparation of amide-linked analogs used in SAR mapping and molecular scaffold optimization. Aromatic side-chain chemistry supports hydrophobic contact modeling and can be leveraged during medicinal chemistry intermediate preparation and combinatorial library synthesis.
4. Chiral Intermediate For Synthesis
H-D-Phg-OEt · HCl functions as a chiral amino acid intermediate for stereoselective synthesis routes targeting D-phenylglycine-containing motifs. The compound's chiral center and ester-protected carboxyl group allow it to be carried through multi-step sequences while maintaining stereochemical integrity, which is important for downstream derivatization into acids, amides, or activated intermediates. The aromatic side chain can be retained as a structural element during transformations, enabling consistent scaffold assembly for research-grade chemical libraries and process chemistry intermediate preparation. The hydrochloride salt form supports practical handling as a defined starting material in chiral building block manufacturing and subsequent functional group interconversions.
5. Analytical Research Standards
H-D-Phg-OEt · HCl is utilized in analytical research as a stereochemically defined amino acid ester reference material for method development and characterization of peptide-like compounds. The presence of the D-phenylglycine motif and the ester group supports targeted detection strategies in chromatographic and mass spectrometric workflows when monitoring protected amino acid derivatives, coupling intermediates, or deprotection outcomes. Hydrochloride salt formation can improve reproducibility of sample preparation for analytical comparisons across stereoisomeric or derivative series. Accurate use of this chiral building block supports quality control of synthetic sequences and verification of stereochemical incorporation in amino acid chemistry and peptide science studies.
6. Pharmaceutical Intermediate Preparation
H-D-Phg-OEt · HCl can be employed in pharmaceutical intermediate preparation where a D-amino acid ester is needed to construct defined peptide or peptidomimetic fragments. The α-amino functionality and the ester-protected carboxyl group provide a controlled platform for conversion into amide-forming intermediates and for subsequent transformations toward C-terminal modifications. The aromatic side chain contributes to scaffold definition during downstream assembly of drug-like candidates and related research materials, supporting consistent synthetic routes for fine chemical production. The compound's role as a chiral, protected amino acid derivative aligns with industrial process chemistry needs for stereodefined intermediate supply and reliable downstream coupling compatibility.
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