Boc-(3S,4S)Sta-OH is a Boc-protected amino acid derivative featuring the Sta side-chain framework and specified (3S,4S) stereochemistry. The molecule contains an amino functionality masked as a tert-butoxycarbonyl (Boc) carbamate and a free carboxylic acid (-COOH), with the substituted ring system providing defined stereochemical constraints relevant to structure-activity and conformational studies. In peptide chemistry, this protected analogue is employed as a building block in stepwise assembly where the Boc group helps control chemoselectivity by suppressing undesired amine reactivity while the carboxyl group serves as the acylation handle for coupling into larger peptide derivatives.
CAT No: CP25915
CAS No:58521-49-6
Chemical Name:(3S,4S)-N-t-Butyloxycarbonyl-statine, (3S,4S)-3-Hydroxy-4-Boc-amino-6-methyl-heptanoic acid
Boc-(3S,4S)Sta-OH is a Boc-protected amino acid building block derived from a stereochemically defined, non-proteinogenic side-chain scaffold, supplied as a protected intermediate for peptide and peptidomimetic synthesis. The presence of the Boc group enables controlled N-terminus handling during stepwise assembly, while the (3S,4S) stereochemical definition supports downstream construction of conformationally biased or stereochemically constrained peptide motifs. As a protected amino acid, it is primarily used in synthetic workflows where precise stereochemistry and orthogonal functional-group compatibility are required for reliable sequence assembly.
1. Stereodefined Peptide Building
Boc-(3S,4S)Sta-OH is used by custom peptide synthesis groups and medicinal chemistry teams to incorporate a stereochemically constrained residue into peptide sequences and peptidomimetic scaffolds. The defined (3S,4S) configuration is particularly valuable when preserving stereochemical integrity is necessary for structure-activity relationship studies, conformational bias, or when building blocks are selected to control three-dimensional presentation of side-chain functionality. The Boc-protected amino terminus supports reliable segment coupling strategies in stepwise peptide assembly, helping researchers generate consistent analog series for downstream biological and biophysical evaluation.
2. Peptidomimetic SAR Intermediate
Boc-(3S,4S)Sta-OH serves as a pharmaceutical-intermediate style amino acid derivative for peptidomimetic development, where stereodefined, non-proteinogenic residues are frequently introduced to tune properties such as backbone geometry and side-chain orientation. Organic synthesis groups developing analog libraries use this building block to prepare defined intermediates that can be carried forward into larger coupling sequences, enabling rapid generation of structural variants while maintaining the stereochemical pattern at the key chiral centers. In medicinal chemistry workflows, this type of protected amino acid is commonly selected to reduce ambiguity in downstream assembly and to support reproducible synthesis of constrained analogs.
3. Protected Residue Library Synthesis
Boc-(3S,4S)Sta-OH is applied in the preparation of protected-residue libraries for research-grade peptide and peptidomimetic manufacturing, including academic and industrial process development settings. The Boc protection pattern supports controlled handling of the amino functionality during iterative synthesis steps, which is important when building complex sequences or when preparing multiple protected intermediates for parallel coupling. Teams using automated or semi-automated peptide assembly workflows often rely on such stereodefined protected amino acid building blocks to maintain consistency across batches and to streamline the procurement of standardized residues for analog production.
4. Chiral Intermediate for Analog Assembly
Boc-(3S,4S)Sta-OH is also used as a chiral amino acid intermediate in stereoselective analog construction, where maintaining the (3S,4S) stereochemical identity is a key requirement for meaningful structure-function comparisons. Synthetic chemists incorporate this building block into larger frameworks to ensure that stereochemical outcomes are locked early in the synthesis route, reducing the risk of stereochemical drift during later-stage transformations. This makes Boc-(3S,4S)Sta-OH a practical choice for teams building constrained chiral motifs that require defined stereochemistry for subsequent coupling, purification, and characterization workflows.
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