erythro-D-Phenyserine is a D-configured, non-proteinogenic amino acid derivative in which the side chain bears a phenyl substituent and an additional hydroxyl-bearing stereogenic relationship consistent with an erythro diastereomeric arrangement. The molecule contains both an amino group and a carboxyl group, enabling it to exist as a zwitterion under appropriate conditions, while the hydroxyl functionality on the side chain provides hydrogen-bonding and polarity that can influence peptide incorporation and conformational preferences. In peptide chemistry and chemical biology research, erythro-D-Phenyserine is employed as a stereochemically defined building block for structure-activity studies, backbone or side-chain functionalization of synthetic peptides, and analytical method development involving non-natural amino acid analogues.
CAT No: CP17206
erythro-D-Phenyserine is a D-configured serine-derived amino acid featuring an erythro relationship between the side-chain hydroxymethyl group and the benzylic carbon bearing the phenyl substituent. The molecule contains a primary amino functionality and a carboxylic acid (or, depending on the exact supplied form, a carboxyl-protected/activated equivalent), enabling standard amino acid coupling chemistry while preserving a stereogenic center that can be tracked through downstream transformations. The side-chain hydroxyl group supports selective derivatization for protecting-group strategies and for tuning polarity, hydrogen-bonding capacity, and reactivity toward esterification or ether formation. The benzylic phenyl substituent increases aromatic reactivity and supports use as a chiral building block for generating phenyl-substituted amino acid derivatives and peptide analogs with defined stereochemistry.
1. Peptide Synthesis
erythro-D-Phenyserine serves as a chiral amino acid building block for peptide coupling workflows in research-grade peptide synthesis. The amino acid backbone participates in amide bond formation, while the side-chain hydroxyl enables orthogonal protection strategies that can be carried through N-protection, coupling, and later deprotection steps to control chemoselectivity during sequential assembly. The erythro stereochemical relationship and D-configuration allow stereochemically defined incorporation into peptide sequences, supporting the construction of stereopure peptide analogs and constrained side-chain architectures. Downstream peptide products can be used to probe backbone/side-chain recognition, generate reference materials for analytical method development, and support scaffold diversification in medicinal chemistry programs.
2. Side-Chain Functionalization
erythro-D-Phenyserine is suitable for side-chain modification routes where the serine-derived hydroxyl group functions as a handle for derivatization. The presence of the benzylic phenyl substituent alongside a stereogenic center enables controlled conversion of the hydroxymethyl group into protected ethers or esters, or into activated intermediates for further functional group installation. Protecting-group selection can be aligned with peptide-compatible strategies, allowing hydroxyl masking during coupling and selective unmasking afterward to generate free hydroxyl-containing analogs or to introduce alternative substituents. Resulting derivatives can serve as intermediates for chiral building block libraries, stereochemically defined probes for chemical biology, and starting points for functionalized peptidomimetics.
3. Chiral Amino Acid Intermediate
erythro-D-Phenyserine functions as a chiral amino acid intermediate for stereoselective synthesis of phenyl-substituted amino acid derivatives and related chiral building blocks. The D-configuration and erythro stereochemistry provide a fixed stereochemical template that can be retained or selectively transformed during downstream functionalization, including conversion of the carboxyl group to activated esters or amide-forming derivatives. The aromatic phenyl moiety can be leveraged for constructing additional aromatic or benzylic substitution patterns while maintaining stereochemical integrity at the amino acid center. The resulting chiral intermediates can feed fine chemical synthesis, chiral auxiliary-like workflows, and process chemistry routes that require defined stereochemical outcomes for downstream coupling or derivatization.
4. Chemical Biology Probes
erythro-D-Phenyserine can be applied in chemical biology research as a stereodefined amino acid component for building recognition probes and biomolecule-interacting peptide analogs. The hydroxyl-bearing side chain supports conjugation-compatible derivatization, including generation of functional groups that can participate in linker installation or affinity-tag attachment while preserving the D/erythro stereochemical signature. The phenyl substituent provides a hydrophobic/aromatic element that can influence binding interactions and can be used to tune molecular recognition in peptide-based probes. Downstream probe constructs can be utilized for studying structure-function relationships, mapping binding preferences, and generating reference standards for stereochemical analysis in biochemical research workflows.
5. Pharmaceutical Manufacturing Intermediates
erythro-D-Phenyserine is suitable as a manufacturing-oriented intermediate for producing protected amino acid derivatives used in peptide and peptidomimetic synthesis at scale. The amino acid functionality supports conversion into N-protected and/or carboxyl-activated forms, while the hydroxyl group can be managed through protection and deprotection sequences that align with industrial peptide coupling chemistries. The stereochemical defined D-erythro framework aids in controlling stereopurity through downstream transformations, which is relevant when preparing chiral intermediates for complex molecule assembly. Process chemistry routes can employ this compound to generate consistent, stereochemically specified building blocks for specialty chemical production and pharmaceutical intermediate preparation.
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