Boc-D-HPip-OH is a Boc-protected amino acid derivative featuring a D-configured 4-hydroxypiperidine (HPip) side chain attached to the amino acid α-carbon. The molecule contains a carbamate-protected amino group (Boc) and a free carboxylic acid, while the HPip ring bears a hydroxyl functional group that can participate in hydrogen bonding and provides a polar handle for further derivatization. As a protected amino acid building block, it is used in peptide and peptidomimetic synthesis to control chemoselectivity at the amine during stepwise coupling and to introduce the hydroxyl-bearing HPip residue for structure-activity studies and chemical biology labeling strategies.
CAT No: CP25792
CAS No:351410-32-7
Synonyms/Alias:351410-32-7;(R)-1-Boc-2-piperidineaceticacid;(R)-(1-Boc-piperidin-2-yl)-aceticacid;(R)-N-Boc-2-piperidineaceticacid;AmbotzBAA6310;PubChem11640;AC1LTT7U;SCHEMBL5781434;CTK1C2047;MolPort-000-002-707;ZINC1436071;ANW-28084;(R)-1-Boc-piperidin-2-ylaceticacid;(R)-N-Boc-2-carboxymethyl-piperidine;AKOS016843461;CB-1113;RP28589;(R)-(1-boc-piperidin-2-yl)aceticacid;AJ-25962;AK-34806;HE077802;KB-02613;RT-005635;FT-0690528;V5415
Chemical Name:(R)-N-t-Butyloxycarbonyl-piperidine-2-acetic acid, Boc-D-Homopipecolic acid
Boc-D-HPip-OH is a D-configured, Boc-protected homoproline (HPip) amino acid building block designed for peptide and peptidomimetic synthesis where a constrained, ring-containing side chain is required. The Boc group provides an N-terminal protecting strategy compatible with standard protected amino acid workflows, while the secondary cyclic side chain supports incorporation into sequences that benefit from stereodefined conformational bias. As a chiral, protected amino acid, it is commonly handled as a synthetic intermediate for assembling longer peptide segments and for preparing stereochemically defined analogs used in structure-activity relationship studies and chemical biology reagent development.
1. Peptide Segment Building
Boc-D-HPip-OH is used as an N-Boc-protected amino acid building block for constructing peptide segments and peptide analogs that incorporate D-HPip residues. Researchers performing custom peptide synthesis rely on the Boc protection to maintain orthogonality during stepwise assembly and to control the reactivity of the amino functionality while the cyclic side chain is carried through the sequence. This product is particularly valuable when the D-configuration and ring-constrained homoproline side chain are needed to tune backbone geometry and to generate stereodefined peptide libraries for downstream biological or biophysical evaluation.
2. Peptidomimetic SAR Development
Boc-D-HPip-OH supports medicinal chemistry workflows focused on peptidomimetic development and structure-activity relationship (SAR) studies where non-proteinogenic residues are introduced to modulate conformation and local sterics. In practice, medicinal chemistry teams and peptide chemistry groups use this protected D-amino acid to prepare analog series that differ specifically at the HPip position, enabling systematic comparison of sequence effects without changing other residues. The cyclic homoproline framework helps maintain a defined three-dimensional presentation of the side chain, making Boc-D-HPip-OH a practical choice for generating stereochemically consistent analogs for SAR screening campaigns and mechanistic probe optimization.
3. Stereodefined Intermediate Synthesis
Boc-D-HPip-OH is also used as a stereochemically defined intermediate for preparing further protected amino acid derivatives and peptide coupling-ready fragments. Because the amino group is protected as Boc, the compound can be advanced through controlled derivatization steps within peptide-manufacturing and research synthesis pipelines, while preserving the D-stereocenter and the cyclic side-chain identity. This makes the product useful for teams producing custom building blocks for segment condensation, modified peptide construction, and rapid iteration of protected-residue inventories used in both academic peptide chemistry and industrial peptide intermediate development.
3. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes
5. TMEM16F and dynamins control expansive plasma membrane reservoirs
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