erythro-DL-Phenyserine is a stereochemically defined phenylserine derivative in which the amino acid backbone bears a benzyl-substituted side chain, classifying it as a serine analog with an additional aromatic functionality. The molecule contains both an amino group and a carboxyl group, and the erythro designation specifies the relative stereochemistry of the two stereogenic centers present in the side chain and backbone region, while the DL notation indicates a racemic mixture of the corresponding enantiomeric forms. As a non-standard amino acid suitable for peptide and small-molecule synthesis, it provides an aromatic side chain for structure-activity studies, chemical labeling strategies, and the preparation of modified amino acid building blocks where serine-like functionality and phenyl substitution are required.
CAT No: CP17204
erythro-DL-Phenyserine is a DL stereochemical mixture of a phenyl-substituted serine analog in which the side chain bears a hydroxymethyl group and a chiral relationship consistent with the erythro configuration. The molecule contains the amino acid core with a primary amine and a carboxylic acid, enabling standard amino acid coupling chemistry while retaining a benzylic phenyl group that can influence conformational preferences and reactivity. The free hydroxyl and carboxyl functionalities support derivatization and protection strategies commonly used in protected amino acid synthesis, and the benzylic stereocenter provides a handle for stereochemical control during downstream transformations. As an amino acid-based intermediate, erythro-DL-Phenyserine can be used to construct peptide-like architectures, to generate chiral derivatives for analytical or synthetic studies, and to access functionalized phenylserine motifs after selective functional group manipulation.
1. Peptide Synthesis
erythro-DL-Phenyserine supports peptide building block preparation for solution-phase or solid-phase peptide synthesis where the free carboxylic acid and amino group participate in amide bond formation. The serine-derived hydroxyl enables side-chain protection strategies such as O-alkyl or O-acyl masking to prevent competing reactions during coupling and deprotection cycles. The erythro stereochemical relationship and the benzylic phenyl substituent can be leveraged to probe stereodependent conformations in peptide analogs and to generate phenylserine-containing sequences for structure-activity relationship studies. Downstream, protected derivatives of erythro-DL-Phenyserine can be incorporated as single-residue units to access peptide fragments, peptidomimetics, and sequence-defined intermediates for biochemical research.
2. Amino Acid Derivatization
erythro-DL-Phenyserine is suitable for amino acid derivatization workflows that exploit its hydroxyl, amine, and carboxylic acid functional groups to generate targeted functionalized analogs. Side-chain hydroxyl chemistry can enable phosphorylation-mimetic motifs, ether formation, or carbamate formation for controlled reactivity in subsequent coupling steps. The benzylic phenyl substituent can be used to access aromatic-substituted derivatives used in chemical biology probes, conformationally constrained scaffolds, or chromatographic standards. Carboxyl activation and amine functionalization can further provide ester, amide, or activated ester intermediates that feed into downstream synthetic organic chemistry and peptide coupling chemistry.
3. Chiral Building Block Development
erythro-DL-Phenyserine serves as a chiral amino acid intermediate platform where stereochemical outcomes can be managed through resolution, stereoselective derivatization, or conversion to diastereomeric protected derivatives. The erythro stereochemistry and the presence of a benzylic phenyl group allow formation of stereochemically informative intermediates for enantiomer separation strategies and for building blocks used in stereocontrolled synthesis. The amino acid core supports conversion to N-protected forms and selective O-protection of the hydroxyl to maintain stereochemical integrity during coupling and functional group interconversions. Resulting enantiomerically enriched or stereodefined derivatives can then be used in peptide analog construction, chiral SAR studies, and stereochemical method development in fine chemical synthesis.
4. Chemical Biology Probes
erythro-DL-Phenyserine can be applied to chemical biology research where phenylserine-like residues are incorporated into labeling constructs or affinity-reactive intermediates. The hydroxymethyl side chain supports conjugation chemistry through protected-to-free hydroxyl conversion, enabling attachment of linkers, fluorophores, or affinity handles while preserving the amino acid backbone for controlled incorporation into peptide scaffolds. The primary amine and carboxyl group allow generation of activated intermediates for bioconjugation-compatible coupling to biomolecule-reactive moieties. Downstream use can include probe synthesis for studying residue-specific recognition, mapping binding interfaces in peptide-based systems, or preparing analytical standards for monitoring incorporation of phenylserine analogs.
5. Pharmaceutical Intermediate Preparation
erythro-DL-Phenyserine is relevant to pharmaceutical intermediate preparation because its amino acid functionality can be transformed into protected amino acid derivatives that integrate into medicinal chemistry and peptidomimetic synthesis. The hydroxyl group supports selective protection and later functional group unveiling, enabling controlled introduction of polar substituents or side-chain modifications during route design. The carboxylic acid can be activated for amide bond formation with drug-like fragments, while the amino group can be protected to prevent undesired reactions during multi-step syntheses. Industrially, erythro-DL-Phenyserine-derived intermediates can serve as feedstocks for manufacturing routes that require amino acid-based stereochemical motifs and robust peptide coupling compatibility.
6. Process Chemistry Intermediates
erythro-DL-Phenyserine can be employed in process chemistry intermediate preparation where predictable amino acid protection, activation, and coupling steps are required for scalable synthesis. The combination of a benzylic phenyl substituent with a serine-derived hydroxymethyl group provides a stable platform for controlled functional group interconversions under standard synthetic organic conditions. The ability to convert the amino group and hydroxyl into protected forms supports manufacturing-friendly sequences that minimize side reactions and enable sequential deprotection to reveal specific reactive sites. Downstream, protected erythro-DL-Phenyserine derivatives can be used to manufacture peptide-like intermediates and functionalized amino acid building blocks for specialty chemical production and industrial fine chemical synthesis.
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