erythro-L-Phenyserine is an amino acid derivative classified as a serine analogue in which the side chain bears a phenyl substituent, forming a stereochemically defined erythro relationship between the side-chain hydroxyl-bearing carbon and the amino-bearing carbon. The molecule contains a primary amino group and a carboxyl group, with the side-chain hydroxyl providing hydrogen-bonding and nucleophilic alcohol functionality while the L designation indicates the configuration at the amino acid stereocenter. erythro-L-Phenyserine is used as a defined building block for peptide and amino acid derivative synthesis and for structure-activity or chemical biology studies that require incorporation or labeling of a phenyl-substituted serine motif.
CAT No: CP17205
Erythro-L-Phenyserine is a chiral serine-derived amino acid analog featuring an erythro stereochemical relationship between the amino-bearing carbon framework and the side-chain hydroxymethyl group, with a benzyl-substituted phenyl group defining a rigid, aromatic-rich side chain. The molecule contains a primary amino functionality and a carboxylic acid (or acid form in typical handling), enabling salt formation and standard amino acid coupling chemistry, while the side-chain hydroxyl supports derivatization to ethers, esters, or protected alcohol intermediates. The stereodefined arrangement and aromatic substituent influence conformational preferences during peptide bond formation and subsequent fragment assembly. As a chiral amino acid intermediate and peptide building block precursor, erythro-L-Phenyserine can be protected at the amine and/or hydroxyl to control chemoselectivity and to support downstream transformations in peptide synthesis and synthetic organic chemistry.
1. Peptide Synthesis
Erythro-L-Phenyserine is applied in peptide synthesis as an amino acid building block that can be incorporated into peptide chains to introduce a stereodefined serine-like hydroxyl and a phenyl-substituted side chain. The amino and carboxyl functionalities enable peptide coupling using standard protected amino acid strategies, while the side-chain hydroxyl can be masked as an ether or ester to prevent side reactions during N-terminal activation and amide bond formation. The erythro stereochemistry helps maintain stereochemical integrity through coupling and deprotection steps when orthogonal protecting groups are selected. Resulting peptide analogs can be used for structure-activity relationship studies and for generating hydroxyl-bearing, aromatic side-chain variants that participate in hydrogen bonding and hydrophobic/aromatic interactions.
2. Side-Chain Functionalization
Erythro-L-Phenyserine is utilized for side-chain functionalization workflows in chemical synthesis and chemical biology, leveraging the serine-derived hydroxymethyl group for controlled derivatization. The hydroxyl can be converted to protected forms for selective peptide assembly, then later transformed into reactive handles such as activated esters, carbonate derivatives, or ether-linked motifs for conjugation chemistry. The aromatic phenyl substituent provides a handle for tuning polarity and aromatic stacking effects in downstream molecular scaffolds. Functionalized derivatives derived from erythro-L-Phenyserine can serve as intermediates for peptidomimetic construction, molecular probes, and scaffold diversification campaigns where stereochemistry and alcohol reactivity are both required.
3. Chiral Building Block Development
Erythro-L-Phenyserine is suitable for chiral building block development in stereoselective synthesis and process chemistry intermediate preparation. The defined stereocenter(s) and amino acid framework support conversion into N-protected amino acid derivatives and, where needed, protected alcohol intermediates that can be carried through multistep sequences without racemization. The carboxylic acid functionality enables formation of activated esters or coupling-ready derivatives, supporting controlled incorporation into larger chiral targets. Downstream use includes preparation of chiral peptide fragments, chiral non-peptide amino acid analogs, and stereochemically defined intermediates used in fine chemical synthesis and industrial chemical manufacturing routes.
4. Bioconjugation Chemistry
Erythro-L-Phenyserine is applied in bioconjugation chemistry as a stereodefined amino acid-derived precursor that can be converted into conjugation-ready hydroxyl-bearing motifs. The side-chain hydroxymethyl group can be protected during peptide or linker assembly, then deprotected to enable subsequent coupling to electrophiles such as activated carbonyls or leaving-group-containing linkers. The aromatic phenyl substituent can influence local hydrophobicity and binding interactions of the conjugate, which may be relevant when designing labeled peptides, affinity reagents, or chemical probes. The resulting conjugation products can serve as biochemical research intermediates for biomolecule labeling and for generating defined amino acid-containing linkers compatible with peptide-based targeting constructs.
5. Structure-Activity And SAR Studies
Erythro-L-Phenyserine is used in structure-activity relationship studies and molecular design efforts to introduce an erythro-configured, hydroxyl-functionalized aromatic side chain into peptide and peptidomimetic scaffolds. The serine-like hydroxymethyl group supports hydrogen-bonding interactions and can be further modified to probe steric and electronic effects, while the phenyl substituent provides aromatic character for assessing binding mode sensitivity. The amino acid backbone compatibility with peptide coupling allows systematic generation of analog series with controlled stereochemistry and functional group placement. SAR-enabled derivatives prepared from erythro-L-Phenyserine can be used to map structure-function relationships in chemical biology workflows and to guide iterative design of amino acid-based molecular scaffolds.
6. Pharmaceutical Intermediate Preparation
Erythro-L-Phenyserine is relevant to pharmaceutical intermediate preparation and specialty chemical production where stereochemically defined amino acid derivatives are required for downstream synthesis. The amino acid functional group set supports conversion into N-protected forms and, when necessary, hydroxyl-protected intermediates that can be processed through peptide coupling or linker assembly steps under controlled chemoselectivity. The aromatic side chain can be retained through protecting-group strategies to furnish stable intermediates for fine chemical synthesis and process chemistry routes. Downstream utility includes preparation of defined peptide fragments, hydroxyl-functionalized chiral intermediates, and amino acid-derived building blocks used to construct larger molecules with controlled stereochemical features.
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