D-4-Hydroxyphenylglycine methyl ester HCl is a D-configured, non-proteinogenic amino acid ester hydrochloride featuring a phenylglycine backbone bearing a para-hydroxyl substituent on the aromatic ring. The molecule contains an esterified carboxyl group (methyl ester) and a free amino functionality present as the hydrochloride salt, with the side-chain phenolic hydroxyl providing a hydrogen-bonding and potential conjugation handle while the D stereochemistry is retained at the amino acid carbon. This amino acid derivative is used in peptide and amide synthesis as a protected/functionalized building block for introducing the 4-hydroxyphenylglycine motif, as well as in structure-activity and chemical biology studies where the phenolic group and ester form support controlled downstream transformations and analytical characterization.
CAT No: CP09804
CAS No:57591-61-4
Synonyms/Alias:(S)-2-(((Benzyloxy)carbonyl)amino)-6-ureidohexanoicacid;57533-91-2;MolPort-027-836-066;8478AB;ZINC71788259;AK117421;AJ-118553;KB-210851
D-4-Hydroxyphenylglycine methyl ester HCl is a chiral amino acid ester hydrochloride featuring the D-configuration at the α-carbon and a para-hydroxyl substituent on the phenyl side chain. The molecule combines a methyl ester at the carboxylate position with a protonated amine salt, which modulates nucleophilicity and supports controlled conversion into peptide-ready derivatives. The phenolic hydroxyl can participate in hydrogen bonding and can be selectively protected or activated for downstream coupling and aromatic functionalization. The overall reactivity profile makes it suitable as a stereodefined chiral amino acid intermediate and as a precursor to protected amino acid building blocks for peptide and peptidomimetic synthesis.
1. Peptide Synthesis
D-4-Hydroxyphenylglycine methyl ester HCl is used in peptide synthesis workflows as a chiral amino acid ester hydrochloride that can be converted into an N-protected, peptide-coupling-compatible derivative. The D-stereocenter enables stereochemically defined incorporation into peptide chains, while the phenolic hydroxyl can be masked with an appropriate protecting group to prevent side reactions during amide bond formation. The methyl ester functionality supports C-terminal strategies such as ester-to-amide conversion or controlled deprotection to generate a carboxylate for coupling. The resulting protected amino acid intermediate can be employed in solid-phase or solution-phase assembly of hydroxylated aromatic peptide analogs and related peptidomimetics.
2. Side-Chain Functionalization
D-4-Hydroxyphenylglycine methyl ester HCl supports side-chain functionalization programs targeting the para-hydroxyl group on the aromatic ring. Phenolic reactivity can be managed through protection/deprotection sequences, enabling transformation into ether, ester, or activated aromatic intermediates while maintaining the D-configuration at the amino acid backbone. The methyl ester and amino salt form can be leveraged to stage chemoselective modifications, including conversion to carboxylate derivatives for subsequent coupling or conjugation steps. Downstream derivatives generated from this intermediate can be applied to structure-activity relationship studies and to the preparation of functionalized peptide fragments used in medicinal chemistry and chemical biology.
3. Chiral Building Block Development
D-4-Hydroxyphenylglycine methyl ester HCl functions as a chiral amino acid intermediate for stereoselective synthesis of D-configured aromatic glycine analogs. The hydrochloride salt form provides a practical handle for controlled N-protection chemistry, while the methyl ester allows tuning of reactivity for intermediate isolation and downstream activation. The para-hydroxy substituent provides an additional stereochemically informative functional group that can influence conformational behavior in peptide scaffolds and can be incorporated into chiral molecular design strategies. The compound can therefore be used to prepare protected D-4-hydroxyphenylglycine derivatives for fragment coupling, library synthesis, and peptidomimetic construction where stereochemical fidelity is required.
4. Chemical Biology Probes
D-4-Hydroxyphenylglycine methyl ester HCl can be applied in chemical biology research to generate hydroxylated aromatic peptide probes and conjugation-ready fragments. The phenolic hydroxyl enables selective derivatization into linkers or handles for bioconjugation chemistry, while the amino acid ester and amino salt support staged conversion into amide-forming or coupling-capable species. The D-configuration can be used to tune metabolic stability and recognition properties of peptide-like constructs used in assay development and biomolecular interaction studies. Prepared derivatives from this intermediate can be incorporated into molecular probes for monitoring binding events, mapping interaction motifs, or constructing labeled peptide analogs compatible with downstream analytical workflows.
5. Pharmaceutical Intermediate Preparation
D-4-Hydroxyphenylglycine methyl ester HCl is suitable for pharmaceutical intermediate preparation where controlled stereochemistry and functional-group compatibility are required. The protected-amino acid strategy can be implemented by converting the amine salt into an N-protected form and managing the phenolic hydroxyl through protection during peptide coupling and intermediate handling. The methyl ester allows C-terminal functional group staging, supporting conversion to activated carboxylate forms or direct transformation into amide-linked intermediates used in process chemistry. The compound's defined D-configuration and aromatic hydroxyl functionality make it a practical feedstock for manufacturing routes that require hydroxylated amino acid building blocks and peptidomimetic precursors.
6. Analytical Standard Development
D-4-Hydroxyphenylglycine methyl ester HCl can serve as an analytical reference material precursor for method development and characterization of D-configured hydroxylated amino acid derivatives. The presence of both an ester and a phenolic hydroxyl enables generation of well-defined standards after controlled derivatization or protection, supporting LC-MS, HPLC, or NMR-based identification of related intermediates. The hydrochloride salt form improves handling consistency for analytical workflows that require reproducible sample preparation from amino acid ester salts. Prepared standards and derivative forms derived from this compound can be used to support impurity profiling, stereochemical assignment of peptide building blocks, and quality control of amino acid intermediate streams in fine chemical synthesis.
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