(2R,3S)-Fmoc-3-phenylisoserine is an Fmoc-protected, non-natural amino acid derivative bearing a side chain derived from isoserine with a phenyl substituent, classed as a protected amino acid used for peptide chemistry. The molecule contains an Fmoc carbamate protecting the α-amino group and a free carboxylic acid, with stereochemistry specified as (2R,3S) and a side-chain hydroxyl functionality that can participate in hydrogen bonding and provide a handle for further derivatization or controlled reactivity during coupling. In synthetic workflows such as solid-phase or solution-phase peptide synthesis, it functions as a building block for introducing the phenylisoserine motif into peptides and for structure-activity or chemical biology studies that require a defined, stereochemically characterized hydroxyl-bearing residue.
CAT No: CP26879
CAS No:252206-27-2
Synonyms/Alias:(2R,3S)-3-(Fmoc-amino)-2-hydroxy-3-phenyl-propanoic acid
(2R,3S)-Fmoc-3-phenylisoserine is an Fmoc-protected amino acid building block designed for incorporation into peptide chains during protected-amino-acid synthesis workflows. Its stereodefined backbone and phenyl-substituted side chain provide a rigid, hydrophobic motif that is commonly used to probe structure-activity relationships, conformational preferences, and local steric effects in peptide and peptidomimetic design. The Fmoc group enables standard base-mediated deprotection strategies used in automated solid-phase peptide synthesis, making this reagent a practical choice for library and lead-optimization studies.
1. Solid-Phase Peptide Synthesis
(2R,3S)-Fmoc-3-phenylisoserine is used as a side-chain-bearing, stereodefined building block for solid-phase peptide synthesis where automated coupling and controlled deprotection are required. Peptide chemistry groups incorporate this residue to introduce a phenyl-substituted isoserine-derived side chain that can influence hydrophobic packing and backbone/side-chain sterics in the growing sequence. Researchers developing constrained or SAR-focused peptide series often select this Fmoc amino acid to systematically vary residue identity while keeping the synthetic handling consistent with established SPPS workflows.
2. Peptide Library And SAR Studies
(2R,3S)-Fmoc-3-phenylisoserine supports peptide library construction and medicinal chemistry optimization by enabling site-specific placement of a phenyl-bearing, stereochemically defined residue. In structure-activity relationship studies, this building block helps chemists evaluate how changes in side-chain bulk and aromatic character affect properties such as conformational behavior and interaction patterns within a target binding pocket. Because the Fmoc protection is compatible with common peptide assembly pipelines, it is frequently used when parallel synthesis of multiple analogs is required to map structure-property relationships efficiently.
3. Peptidomimetic Intermediate Development
(2R,3S)-Fmoc-3-phenylisoserine is also applied as a protected amino acid intermediate for downstream conversion into peptidomimetic scaffolds and non-natural residue analogs used in drug discovery chemistry. Synthetic teams leverage the stereodefined Fmoc-protected framework to access phenyl-substituted isoserine-derived fragments that can be further functionalized during the preparation of modified backbones or side-chain analogs. This use case is particularly common in programs that require consistent stereochemical control across iterative design cycles, while maintaining compatibility with peptide-derived synthetic logic.
4. Analytical Reference For Method Development
(2R,3S)-Fmoc-3-phenylisoserine is used in analytical method development and characterization workflows for peptide synthesis, including monitoring of coupling efficiency, deprotection performance, and impurity profiling of Fmoc-based intermediates. Analytical chemists and process development teams may include this defined building block as a reference material when validating LC methods for peptide synthesis components or when establishing retention-time/fragmentation expectations for stereodefined, Fmoc-protected amino acid residues. Its defined identity and protection pattern make it a practical standard for troubleshooting and documentation in peptide manufacturing research settings.
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