Ac-DL-Asp-OH is an amino acid derivative consisting of an acetylated aspartic acid scaffold (Asp) bearing a free carboxylic acid, where "DL" indicates a racemic mixture of stereoisomers. The molecule contains an N-acetyl amide at the amino terminus and a side-chain carboxyl group characteristic of aspartate, with the acetylation reducing the basicity and chemoselectively differentiating the amine from the acidic functionalities. In research workflows, this compound is used as a structurally defined aspartate derivative for peptide synthesis studies, solution-phase or analytical method development involving protected/derivatized amino acid building blocks, and as a reference substrate for examining how N-acetylation influences reactivity and labeling behavior.
CAT No: CP26886
CAS No:2545-40-6
Synonyms/Alias:N-Acetyl-DL-asparticacid;2-Acetamidosuccinicacid;2545-40-6;DL-Asparticacid,N-acetyl-;Asparticacid,N-acetyl(R,S);2-acetamidosuccinate;2-acetamidobutanedioicacid;SMR000857232;D-Asparticacid,N-acetyl-;Prestwick_712;ACMC-20mswo;Ac-DL-Asp-OH;Asparticacid,N-acetyl-;N-Acetylasparticacid#;AC1L3YNL;AC1Q1KFW;AC1Q5KYA;Prestwick0_000415;Prestwick1_000415;Prestwick2_000415;Oprea1_041445;2-(Acetylamino)succinicacid;MLS001333103;MLS001333104;A5625_SIGMA
Ac-DL-Asp-OH is an acetylated, racemic (DL) aspartic acid derivative supplied as the free acid, combining a protected N-terminus (acetyl) with the native side-chain carboxylic acid of Asp. This structure makes it a convenient, well-defined amino acid building block for preparing aspartate-containing peptides and for generating acetylated Asp residues in synthetic and analytical workflows where control of the N-acetyl state is required. Because the product is provided as a DL mixture, it is frequently used when stereochemical purity is not the primary experimental variable, such as in method development, reference material preparation, and intermediate synthesis.
1. Acetylated Asp Residue Synthesis
Ac-DL-Asp-OH is used in peptide and peptidomimetic synthesis as an aspartate building block carrying an N-acetyl modification, enabling incorporation of an Ac-protected Asp motif into longer sequences. Researchers developing N-terminally acetylated peptide fragments, substrate analogs, or standards for downstream characterization often select this derivative to ensure the acetylated amino terminus is present from the outset. In custom peptide manufacturing and medicinal chemistry research, the racemic nature supports workflows where relative stereochemistry is not resolved at the building-block stage, such as exploratory library synthesis or comparative studies of backbone modifications.
2. Peptide Fragment and Intermediate Preparation
Ac-DL-Asp-OH is commonly employed as a defined intermediate for assembling aspartate-containing segments through stepwise sequence construction, including the preparation of acetylated Asp-containing coupling partners and protected/activated derivatives generated in-house. Pharmaceutical intermediate development groups use this material to standardize the N-acetyl state of the Asp residue before further functionalization toward larger intermediates, such as peptide-like linkers or constrained aspartate motifs used in SAR campaigns. The presence of both the acetylated amino group and the side-chain carboxylic acid supports downstream derivatization strategies used to control charge and reactivity during fragment assembly.
3. Analytical Standard and Method Development
Ac-DL-Asp-OH is frequently used as an analytical reference material for LC-MS and related characterization workflows that require an authentic acetylated aspartate species. Laboratories performing peptide digestion, fragment analysis, or impurity profiling may include this compound to track acetylated Asp-related signals and to support identification and quantitation of acetylated amino acid derivatives generated during sample handling or synthesis. The DL composition is particularly practical for method development and routine QC-style checks where the goal is consistent detection of the acetylated Asp form rather than stereospecific discrimination.
4. Aspartate-Containing Biomaterial Building Blocks
Ac-DL-Asp-OH is also applied in biomaterials and polymer chemistry contexts where an acetylated aspartate functionality is used to introduce aspartate-derived carboxyl chemistry into larger constructs. Materials scientists leverage the side-chain carboxylic acid of Asp to enable subsequent coupling, crosslinking, or incorporation into linker architectures that benefit from carboxyl-bearing motifs and controlled N-acetyl substitution. This derivative is therefore useful in the development of aspartate-functional polymers, peptide-inspired linkers, and surface-modification intermediates where the acetylated amino terminus is part of the designed chemical identity.
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