Boc-D-Abu-OH is a protected amino acid derivative in which D-2-aminobutyric acid (D-Abu) is masked at the amino group with a tert-butoxycarbonyl (Boc) protecting group. The molecule contains a free carboxylic acid functionality and a Boc-protected amino group, with the side chain corresponding to an aminobutyrate framework that supports incorporation into peptide-building sequences while limiting undesired amine reactivity. In peptide chemistry and related synthesis, Boc-D-Abu-OH is employed as a stepwise coupling component or intermediate for preparing modified peptides and amino acid derivatives, and the Boc group provides chemoselective control over amide-bond formation during sequential assembly.
CAT No: CP27128
CAS No:45121-22-0
Synonyms/Alias:45121-22-0;(R)-2-((tert-Butoxycarbonyl)amino)butanoicacid;(R)-N-Boc-2-aminobutyricacid;Boc-D-alpha-aminobutyricacid;BOC-(R)-2-aminobutyricacid;BOC-D-ABU-OH;AmbotzBAA1341;AC1MBSFA;PubChem15613;BOC-D-2-ABU-OH;BOC-D-ABU(2)-OH;KSC235A2L;SCHEMBL1951491;CTK1D5025;BOC-D-2-AMINOBUTYRICACID;MolPort-002-344-032;PNFVIPIQXAIUAY-ZCFIWIBFSA-N;ACN-S002355;N-BOC-D-2-AMINOBUTYRICACID;ANW-41692;ZINC84317435;AKOS015155839;AKOS015910186;AB05557;NE47033
Boc-D-Abu-OH is a Boc-protected D-configured amino acid building block derived from D-α-aminobutyric acid (D-Abu), featuring a stereodefined chiral center and a side chain that is a short aliphatic propyl segment. As a protected amino acid, it is designed for downstream peptide assembly workflows where the N-terminus is masked as a tert-butoxycarbonyl (Boc) carbamate, enabling controlled coupling chemistry while preserving stereochemical integrity. Its compact, aliphatic side chain makes it a common structural element in peptide-like scaffolds and medicinal chemistry intermediates where conformational and steric effects from a short alkyl substituent are required.
1. Boc-Based Peptide Building Block
Boc-D-Abu-OH is used as an N-Boc-protected amino acid building block for custom peptide synthesis and peptide fragment assembly, particularly when D-amino acid incorporation is desired to tune peptide conformation and resistance to enzymatic degradation in chemical biology and medicinal chemistry studies. Researchers performing solution-phase peptide synthesis or segment coupling workflows select this protected D-Abu residue to introduce a short, flexible aliphatic side chain while keeping the amino functionality protected as a Boc carbamate during coupling and purification. The defined D-stereochemistry supports stereocontrolled construction of peptide libraries and stereochemically consistent analog series used in structure-property investigations.
2. D-Amino Acid Scaffold Engineering
Boc-D-Abu-OH supports the preparation of peptide mimetics and stereochemically defined oligomers used in protein engineering research and structure-activity relationship (SAR) development for peptidomimetic leads. Medicinal chemistry groups use D-α-aminobutyric acid residues to modulate backbone stereochemistry and local conformational preferences, and the Boc-protected form streamlines integration into synthetic sequences that require protected amino acid inputs. This reagent is especially relevant when short alkyl side chains are used to probe steric and hydrophobic contributions without introducing additional functional groups that could complicate downstream purification or biological assay readouts.
3. Pharmaceutical Intermediate Development
Boc-D-Abu-OH is commonly deployed as a chiral, protected amino acid intermediate in the synthesis of D-amino acid-containing intermediates for medicinal chemistry programs. Process and development chemists rely on the Boc-protected amino group to enable stepwise construction of amide-containing intermediates while maintaining stereochemical fidelity through multistep sequences. The small aliphatic side chain of D-Abu also aligns with intermediate design strategies where minimal side-chain functionality is preferred to reduce side reactions and to simplify conversion into subsequent coupling partners, protecting-group adjustments, or final scaffold assembly.
4. Chiral Reference Material Synthesis
Boc-D-Abu-OH is used in the preparation of stereodefined standards and analytical reference materials for method development in chiral chemistry and amino acid derivative profiling. Analytical laboratories and method developers incorporate this Boc-protected D-building block into derivatization or reference compound synthesis workflows where controlled stereochemistry and a protected amino functionality are required to generate consistent, well-characterized intermediates. Its defined D-configuration and Boc protection make it useful when downstream analytical readouts depend on stereochemical identity and uniform functional-group protection across a set of comparator compounds.
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