Acetyl-D-2-aminobutyric acid is a D-configured amino acid derivative in which the amino acid backbone corresponds to 2-aminobutyric acid and the α-amino functionality is acetylated, yielding an N-acetylated amino acid rather than a free amino acid. The molecule contains a carboxyl group and an acetyl-protected amino group, with a stereocenter at the 2-position consistent with the D designation and a side chain that is a short, aliphatic propyl-like fragment. In synthesis and analytical workflows, N-acetylated amino acid derivatives such as this compound are used as protected or masked building blocks for controlled peptide coupling chemistry and as chemically defined standards or substrates for studying amino acid reactivity, derivatization behavior, and chromatographic or spectrometric characterization of amino acid forms.
CAT No: CP02903
CAS No:34271-27-7
Synonyms/Alias:(R)-2-Acetamidobutanoicacid;34271-27-7;AC-D-2-ABU-OH;Acetyl-D-2-aminobutyricacid;N-Acetyl-D-butyrine;AC1Q2C6L;Acetyl-D-2-aminobutyricacid;SCHEMBL12064252;CTK1C3423;MolPort-001-792-770;ZINC4760978;4099AB;ANW-58116;AKOS006278501;AJ-52185;AK-87748;Butanoicacid,2-(acetylamino)-,(2R)-;TC-146861
Acetyl-D-2-aminobutyric acid is a D-configured, amino acid derivative in which the amino functionality is acetylated, reducing direct nucleophilicity while retaining a carboxylic acid for downstream conversion. This protected/derivatized form is commonly handled as a chiral building block for stereochemically defined synthesis and as a reagent intermediate where controlled reactivity and the D-stereocenter are important for product consistency.
1. Chiral Building Block Synthesis
Acetyl-D-2-aminobutyric acid is used by medicinal chemistry and process chemistry teams as a stereochemically defined intermediate for assembling D-configured amino acid motifs in peptidomimetic and small-molecule scaffolds. The acetylated amino group provides a convenient "masked" nitrogen during multi-step sequences, helping chemists manage chemoselectivity while maintaining the D-configuration at the 2-position. In practice, it is often selected when the downstream route requires introduction of an amino functionality later, after other functional group transformations have been completed.
2. Peptidomimetic And Amide Formation
Acetyl-D-2-aminobutyric acid supports the preparation of D-substituted amide-containing intermediates used in peptidomimetic development and SAR (structure-activity relationship) workflows. The presence of the carboxylic acid enables coupling chemistry toward amide or ester derivatives, while the acetylated amino group helps avoid premature side reactions that can complicate late-stage functionalization. Researchers developing constrained or stereodefined analogs frequently prefer this type of amino acid derivative to ensure that the stereochemical outcome at the chiral center is consistent across parallel synthesis campaigns.
3. Pharmaceutical Intermediate Development
Acetyl-D-2-aminobutyric acid is employed as a chiral intermediate in the synthesis of specialty pharmaceutical intermediates where reliable stereochemical control and manageable functional-group behavior are required. Process development groups value amino acid derivatives in this format because they can be incorporated into longer synthetic sequences without exposing the free amine too early, which can otherwise lead to salt formation, adsorption issues, or competing reactivity. The compound's defined D-stereochemistry makes it particularly useful when downstream steps demand strict stereochemical fidelity for impurity control and reproducible batch-to-batch performance in research-scale manufacturing.
4. Analytical Reference And Method Support
Acetyl-D-2-aminobutyric acid is also used in analytical method development and characterization work as a stereochemically defined reference material for verifying identity and monitoring transformations of D-2-aminobutyric acid-derived intermediates. Laboratories performing LC-based impurity profiling or intermediate tracking often incorporate such derivatives to distinguish stereochemical variants and to confirm conversion during synthetic sequences. Its derivatized amino functionality can provide a consistent analytical handle for method tuning, especially when free amino acids show broader chromatographic behavior due to ionization and salt effects.
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