[(RS)-2-Carboxy-3-phenylpropionyl]-Leu-OH is a leucine-containing amino acid derivative in which a 2-carboxy-3-phenylpropionyl acyl group is attached to the leucine residue, forming a substituted peptide-like intermediate rather than a free amino acid. The molecule contains both a carboxylic acid on the phenylpropionyl side chain and a carboxylic acid at the leucine α-position, along with an additional amide linkage that connects the acyl group to the leucine nitrogen; the (RS) designation indicates racemic stereochemistry at the acyl-bearing stereocenter when present in the named structure. In synthesis and chemical biology workflows, this structure can serve as a precursor for assembling more complex amino acid derivatives or peptidomimetic motifs, and its dual carboxyl functionality and phenyl-containing side chain support use in conjugation, solubility tuning, and analytical method development for closely related peptide-building blocks.
CAT No: CP26764
CAS No:209127-97-9
Synonyms/Alias:209127-97-9;Glutaryl-Leu-OH;SCHEMBL5654469;AM001316;FT-0643949;[(RS)-2-Carboxy-3-phenylpropionyl]-Leu-OH;[-2-CARBOXY-3-PHENYLPROPIONYL]-LEU-OH;N-((R,S)-2-CARBOXY-3-PHENYLPROPIONYL)-L-LEUCINE;(2S)-2-(2-BENZYL-2-CARBOXYACETAMIDO)-4-METHYLPENTANOICACID
[(RS)-2-Carboxy-3-phenylpropionyl]-Leu-OH is a leucine-containing amino acid derivative featuring a phenylpropionyl-type side-chain bearing an additional carboxyl group, providing both an amino acid motif and a second acidic functionality for downstream coupling and salt formation. The (RS) stereochemical designation indicates a racemic center within the substituted propionyl fragment, making this material particularly useful where stereochemical uniformity is not required for the target intermediate or analytical reference. In practice, this compound is handled as a research-grade building block for assembling more complex peptide-like structures and for preparing defined standards used in method development and characterization workflows.
1. Peptide-Like Building Blocks
[(RS)-2-Carboxy-3-phenylpropionyl]-Leu-OH is used as a specialized amino acid derivative building block in peptide-like synthesis and related coupling workflows, where leucine is incorporated alongside a substituted phenylpropionyl fragment. Researchers developing constrained or modified peptide analogs rely on the presence of two carboxyl groups and the amino acid functionality to enable controlled assembly into longer sequences or into defined fragments for SAR-style studies. The racemic (RS) nature of the substituted center is often leveraged in early-stage library or intermediate preparation when the goal is to access a broader chemical space efficiently rather than to enforce a single stereochemical outcome.
2. Pharmaceutical Intermediate Development
[(RS)-2-Carboxy-3-phenylpropionyl]-Leu-OH serves as a practical intermediate in medicinal chemistry programs that require leucine-derived fragments bearing an extra carboxyl functionality for further derivatization. Process and synthesis teams use such amino acid derivatives to introduce polarity and handleable acidic groups that can be carried through to later stages, including formation of activated derivatives for subsequent coupling steps or conversion into salts for physicochemical tuning during lead optimization. The compound's dual carboxyl character supports downstream transformations typical of pharmaceutical intermediate pipelines, especially when building blocks must be compatible with multi-step organic synthesis and purification strategies.
3. Analytical Standards And Characterization
[(RS)-2-Carboxy-3-phenylpropionyl]-Leu-OH is commonly employed as a defined chemical reference for analytical method development and characterization of peptide-derived or peptide-like intermediates. Analytical teams use leucine-containing derivatives with additional carboxyl functionality to establish retention behavior, fragmentation patterns, and response characteristics in LC-MS workflows, and to verify identity and purity during synthesis scale-up and process troubleshooting. The presence of a stable, well-defined structure with multiple acidic groups makes the compound useful for calibrating or qualifying assays that monitor complex reaction mixtures where amino acid-derived species and related analogs must be distinguished.
4. Chiral Resolution And Derivative Screening
[(RS)-2-Carboxy-3-phenylpropionyl]-Leu-OH is also used in derivative screening and stereochemical follow-up studies where a racemic precursor is intentionally carried forward to evaluate downstream separation, resolution, or derivatization strategies. Medicinal chemistry and chemical biology groups often start from racemic amino acid derivatives to rapidly access a family of downstream compounds, then refine stereochemistry once structure-property relationships become clear. The compound's leucine motif and additional carboxyl group provide functional handles for generating stereochemically informative derivatives and for comparing analytical profiles across resolved or derivatized stereoisomers.
1. Cell-based adhesion assays for isolation of snake venom’s integrin antagonists
2. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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