Boc-D-Pra-OH*DCHA is a Boc-protected D-amino acid derivative of 2,3-diaminopropionic acid (Pra) supplied as a salt with dicyclohexylamine (DCHA), featuring the Boc carbamate on the amino functionality and a free carboxylic acid for further coupling chemistry. The side chain contains an additional amino group that can be protonated and provides a reactive handle for selective derivatization or orthogonal protection strategies, while the D stereochemical designation indicates a defined configuration at the alpha carbon. In peptide and amino acid synthesis workflows, the Boc group supports chemoselective stepwise assembly by suppressing undesired amine reactivity during coupling, and the DCHA salt form can aid handling and reproducible reactivity of the amino acid building block in solution-phase or solid-phase synthesis.
CAT No: CP25953
CAS No:63039-47-4
Synonyms/Alias:63039-46-3;Boc-D-Propargylglycine;(R)-2-((tert-Butoxycarbonyl)amino)pent-4-ynoicacid;N-Boc-2-Propargyl-D-glycine;Boc-D-Pra-OH;SBB016954;Boc-D-Gly(propargyl)-OH;SCHEMBL939477;CTK8B8261;AMKHAJIFPHJYMH-SSDOTTSWSA-N;MolPort-001-758-718;ZINC2379465;ANW-59807;CB-765;AM82636;AN-8493;RTR-021716;AJ-34592;AK-35925;KB-48292;M087;AB0015054;N-(tert-Butoxycarbonyl)-3-ethynyl-D-alanine;M-2057;2-(R)-tert-butoxycarbonylaminopent-4-ynoicacid
Chemical Name:N-alpha-t-Butyloxycarbonyl-D-propargylglycine dicyclohexylamine
Boc-D-Pra-OH*DCHA is a D-configured amino acid building block supplied as a Boc-protected derivative with dicyclohexylamine (DCHA) counterion association, providing a practical, bench-stable form for downstream peptide-manufacturing workflows. The Boc group on the amino functionality supports controlled coupling chemistry, while the side-chain of Pra (2,3-diaminopropanoic acid) offers a strongly functionalized, highly polar handle that is commonly managed during peptide assembly to enable incorporation of charged or interaction-rich motifs.
1. Solid-Phase Peptide Synthesis
Boc-D-Pra-OH*DCHA is frequently selected for solid-phase peptide synthesis workflows where D-amino acid content and side-chain functionality are used to tune peptide conformation, proteolytic stability, or interaction patterns. Peptide synthesis groups use this Boc-protected, D-configured input as a defined residue for stepwise assembly, including in custom peptide synthesis and peptide library construction. The Boc protection is particularly useful for maintaining the amino group's reactivity profile during chain elongation, while the DCHA-associated form can help with handling and reproducible dosing of the amino acid building block in automated or semi-automated peptide workflows.
2. Peptidomimetic And SAR Building Blocks
Boc-D-Pra-OH*DCHA is used in medicinal chemistry and peptidomimetic development to introduce a D-amino acid residue bearing a highly functional side chain, supporting structure-activity relationship (SAR) studies that probe how stereochemistry and side-chain charge density affect peptide-like binding modes. Research groups preparing constrained analogs, stapled or otherwise modified peptide scaffolds, and D-amino acid-containing analog series rely on this reagent to introduce the Pra residue with controlled protection at the backbone nitrogen. In these programs, the Boc-protected format supports reliable intermediate handling before further functionalization or coupling steps that build toward final analogs.
3. Pharmaceutical Intermediate Development
Boc-D-Pra-OH*DCHA serves as a practical intermediate for downstream synthesis of protected or selectively functionalized amino acid derivatives used in process chemistry. Pharmaceutical intermediate developers and contract manufacturing research teams use Boc-protected amino acid inputs to standardize how the amino functionality is presented for subsequent transformations, including conversion into activated coupling partners or incorporation into larger protected fragments. The D-configured stereochemistry and the strongly polar Pra side chain make this reagent particularly relevant when the target intermediate set requires a defined stereochemical outcome and a residue that can later be elaborated under orthogonal protection strategies used in industrial peptide and peptidomimetic manufacturing.
4. Analytical Reference For Peptide Chemistry
Boc-D-Pra-OH*DCHA is also used as a defined chemical reference in analytical method development and method qualification for peptide synthesis and intermediate characterization. Analytical chemistry teams employ this type of Boc-protected, stereodefined amino acid building block to support LC method optimization, impurity profiling, and identity checks for peptide synthesis inputs and partially assembled intermediates. The presence of a controlled protection pattern and a fixed stereochemical configuration helps ensure that retention-time behavior and derivatization outcomes remain consistent when validating workflows for amino acid-derived fragments and protected peptide building blocks.
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