Boc-D-2Abu-OH*DCHA is a protected amino acid derivative in which the amino group of D-2-aminobutyric acid is masked by a Boc (tert-butoxycarbonyl) protecting group while the carboxyl group remains present as a free acid. The molecule contains a chiral center consistent with the "D" designation and features an aliphatic side chain with a terminal methylene, and the "*DCHA" notation indicates formation of a salt or adduct with dicyclohexylamine (DCHA) that modulates handling and physicochemical properties. As a Boc-protected, salt-form amino acid, it is used as a building block for stepwise peptide synthesis and for preparing amino acid-containing intermediates where chemoselective deprotection and controlled coupling are required.
CAT No: CP25698
CAS No:27494-47-9
Synonyms/Alias:27494-47-9;BOC-D-ABU-OHDCHA;Dicyclohexylamine(R)-2-((tert-butoxycarbonyl)amino)butanoate;Boc-D-Abu-OH(dicyclohexylammonium)salt;AC1MBSF7;73876_ALDRICH;73876_FLUKA;MolPort-003-725-607;MolPort-028-751-644;Boc-D-Abu-OHdicyclohexylaminesalt;MFCD00235886;AKOS015920050;AKOS025395636;Boc-D-Abu-OHdicyclohexylammoniumsalt;CS20260;DS-1108;AK-45026;BR-45026;KB-03424;AB0072743;ST2419163;FT-0693722;W5059;S-2382;(R)-2-Boc-amino)butyricaciddicyclohexylaminesalt
Chemical Name:(R)-N-t-Butyloxycarbonyl-2-aminobutyric acid dicyclohexylamine
Boc-D-2Abu-OH*DCHA is a Boc-protected D-2-aminobutyric acid derivative supplied as a dicyclohexylamine (DCHA) salt, combining a stereodefined amino acid building block with an acid/base-handling form that is commonly used for peptide intermediate preparation. The Boc group provides an N-terminal protecting strategy compatible with protected-amino-acid workflows, while the D-configuration supports stereochemical control in downstream peptide synthesis and medicinal chemistry programs that require non-proteinogenic stereodefined residues. This reagent format is frequently selected when reliable handling, consistent coupling performance, and defined stereochemistry are priorities for custom peptide assembly and analog development.
1. Stereodefined Peptide Building Block
Boc-D-2Abu-OH*DCHA is used as a protected amino acid building block for incorporating D-2-aminobutyric acid residues into peptides and peptidomimetic scaffolds. Research groups performing custom peptide synthesis and medicinal chemistry analog development rely on Boc protection to manage N-terminus reactivity during stepwise assembly, while the D-configuration enables controlled placement of stereocenters that can influence conformational preferences and structural features of peptide-like molecules. The DCHA salt form is often chosen to improve practical handling of the amino acid intermediate in peptide synthesis workflows, supporting consistent weighing, transfer, and preparation of coupling-ready materials.
2. Peptide Analog And Library Synthesis
Boc-D-2Abu-OH*DCHA supports the preparation of peptide analogs and residue-scan libraries where non-proteinogenic D-amino acid incorporation is used to probe structure-activity relationships and backbone effects. In hit-to-lead and lead-optimization settings, peptide chemists use stereochemically defined D-2Abu units to generate analog series with systematic variation in residue identity and stereochemistry, enabling downstream evaluation of physicochemical and functional properties in non-clinical research contexts. The Boc-protected, salt-form reagent is particularly useful for parallel synthesis workflows where reproducible intermediate preparation and defined stereochemical content are required across multiple analogs.
3. Pharmaceutical Intermediate Development
Boc-D-2Abu-OH*DCHA is also used as a key pharmaceutical intermediate building block for manufacturing workflows that require protected, stereodefined amino acid fragments. Process development teams and specialty chemical manufacturers incorporate D-2Abu-derived units into larger synthetic sequences, including protected peptide segments and peptide-like intermediates used for further derivatization. The Boc-protected functionality helps maintain chemoselectivity during multistep intermediate construction, while the DCHA salt form supports robust handling in industrial and scale-up environments where solid-state properties and reproducibility of reagent preparation can be important for downstream coupling and purification steps.
4. Non-Proteinogenic Residue Design
Boc-D-2Abu-OH*DCHA is commonly selected in chemical biology and medicinal chemistry projects that design peptide-like molecules containing D-amino acid residues to achieve defined backbone stereochemistry beyond the proteinogenic set. Synthetic chemists use this reagent to introduce a stereochemically controlled 2-aminobutyric acid motif into sequence-defined constructs, including constrained or modified peptide backbones where the D-configuration is a deliberate design element. By providing a protected, stereodefined amino acid intermediate, it streamlines the integration of D-2Abu into custom structures used for mechanistic studies, binding studies, and structure-property exploration in laboratory research programs.
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