Boc-(3S,4S)-AHPPA-OH is a protected, non-natural amino acid derivative bearing a Boc-protected amino terminus and an AHPPA core with defined (3S,4S) stereochemistry. The molecule contains a free carboxylic acid functional group and a side-chain framework that includes additional heteroatom-bearing functionality characteristic of AHPPA, while the Boc group masks the α-amino reactivity to control chemoselectivity during coupling. It is used as a stepwise building block in peptide synthesis and related solid-phase or solution-phase assembly workflows, where the protected amino group supports selective formation of amide bonds to target peptides and amino acid conjugates.
CAT No: CP26012
CAS No:72155-46-5
Synonyms/Alias:BOC-AHPPA-OH;72155-46-5;AmbotzBAA1319;AC1MBSFS;Boc-(3S,4S)-AHPPA;SCHEMBL8787243;(3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOICACID;MolPort-003-725-473;ZINC2539198;6257AH;KM1454;FT-0641396;(3S,4S)-3-Hydroxy-4-(tert-butoxycarbonylamino)-5-phenylpentanoicacid;(3S,4S)-3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoicacid
Chemical Name:(3S,4S)-4-t-Butyloxycarbonylamino-3-hydroxy-5-phenyl-pentanoic acid
Boc-(3S,4S)-AHPPA-OH is a Boc-protected amino acid derivative bearing the AHPPA side chain, supplied as a stereodefined chiral building block for peptide and peptidomimetic synthesis. The presence of the Boc group supports its use as an N-protected amino acid component in protected-amino-acid workflows, while the (3S,4S) configuration provides conformational and stereochemical control in downstream assembly. This reagent is typically selected when a specific chiral amino acid motif is required to construct defined peptide segments or pharmaceutical intermediates.
1. Solid-Phase Peptide Segments
Boc-(3S,4S)-AHPPA-OH is used by peptide synthesis groups to prepare defined peptide segments where a stereochemically controlled AHPPA-containing residue is required. In solid-phase workflows, the N-Boc protection pattern supports incorporation as an amino acid building block during protected-amino-acid assembly, enabling researchers to target sequence-defined oligopeptides and longer peptide constructs with consistent stereochemical identity. This product is particularly relevant for custom peptide synthesis and library-style preparation where the (3S,4S) stereochemistry must be maintained through coupling and purification steps.
2. Peptidomimetic And SAR Intermediates
Boc-(3S,4S)-AHPPA-OH is frequently employed in medicinal chemistry programs that develop peptidomimetics and structure-activity relationship (SAR) series incorporating chiral amino acid motifs. The protected, stereodefined nature of the reagent makes it a practical intermediate for assembling analogs where the AHPPA side chain contributes to conformational bias or specific spatial presentation within a larger scaffold. Teams preparing gram-scale or multi-gram intermediate sets for medicinal chemistry typically value this type of building block for consistent stereochemical outcomes across analog synthesis campaigns.
3. Chiral Building Block For Stereocontrolled Synthesis
Boc-(3S,4S)-AHPPA-OH serves as a stereocontrolled chiral building block for downstream organic synthesis steps that require retention of (3S,4S) configuration. Process and development chemists often select Boc-protected amino acid derivatives when downstream coupling, fragment assembly, or intermediate elaboration depends on reliable stereochemical identity rather than late-stage resolution. The Boc-protected amino functionality also supports its role as a controlled input for constructing larger, functionally defined intermediates used in peptide-derived materials and specialty chemical manufacturing.
4. Pharmaceutical Intermediate Assembly
Boc-(3S,4S)-AHPPA-OH is used in the preparation of protected amino acid intermediates that feed into pharmaceutical intermediate assembly for peptide-like and peptidomimetic chemotypes. Development teams typically incorporate this reagent into multi-step synthetic sequences where the AHPPA motif must be introduced early and carried through subsequent transformations with minimal stereochemical drift. Its protected format supports compatibility with established intermediate-building strategies used in custom synthesis environments and industrial development workflows that require reproducible chiral building blocks.
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