Ac-D-Asn-OH is an N-acetylated, D-configured amino acid derivative consisting of asparagine bearing a free carboxylic acid and an acetylated amino group, where the side chain contains a primary amide. The molecule therefore presents an acetamide functionality at the N-terminus and a side-chain amide capable of hydrogen bonding, while the D stereochemistry at the alpha carbon is retained as specified by the name. Ac-D-Asn-OH is used as a protected or masked asparagine building block in peptide-related synthesis and chemical labeling workflows, where the N-acetyl group helps control chemoselectivity and supports incorporation of an asparagine residue analog into larger amino acid and peptide structures.
CAT No: CP26908
CAS No:26117-27-1
Synonyms/Alias:Nalpha-Acetyl-D-asparagine;26117-27-1;N2-Acetyl-D-asparagine;N-ACETYL-D-ASPARAGINE;Acetyl-D-asparagine;(2R)-2-acetamido-4-amino-4-oxobutanoicacid;AC1Q5JMG;N|A-Acetyl-D-asparagine;AC1L3LH8;2-Acetylamino-succinamicacid;A5250_SIGMA;CHEMBL172478;SCHEMBL1204312;CTK7D2447;HXFOXFJUNFFYMO-SCSAIBSYSA-N;MolPort-002-893-876;ZINC135376;BTB13544;EINECS247-468-4;AR-1K5553;AKOS006240447;AM81556;MCULE-5563097482;AM004162;KB-47101
Ac-D-Asn-OH is an N-acetylated, D-configured asparagine derivative supplied as a free carboxylic acid for peptide and peptidomimetic building workflows. The acetylated amino terminus and the side-chain amide of the asparagine residue make it a useful, pre-functionalized segment for assembling protected or semi-protected peptide sequences while controlling N-terminus reactivity. In practice, researchers use Ac-D-Asn-OH to introduce a D-amino acid residue with an amide side chain that supports hydrogen-bonding interactions and stable conformational contributions in synthetic peptides and peptide-based materials.
1. Dipeptide Segment Building
Ac-D-Asn-OH is frequently used as an N-acetylated D-asparagine building block in peptide assembly where the N-terminus must be capped to suppress undesired coupling or side reactions during segment condensation. Peptide synthesis groups and custom peptide manufacturers incorporate this residue when they want a defined D-amino acid position within a short peptide, peptidomimetic, or peptide mapping construct, with the acetyl group providing a consistent N-terminus environment. The asparagine side-chain amide is retained in the final structure, supporting downstream characterization by MS and facilitating structure-function studies that rely on polar side-chain interactions.
2. Peptidomimetic Conformation Studies
Ac-D-Asn-OH is used in chemical biology and medicinal chemistry research to prepare peptidomimetic scaffolds that include D-amino acid stereochemistry for probing conformational preferences and sequence-dependent properties. Synthetic teams select this derivative when they want to compare D- versus L-configured residues while maintaining the same asparagine side-chain functionality for hydrogen-bonding pattern consistency. The N-acetyl capping also helps standardize termini across analog series, which is valuable for structure-activity relationship style studies focused on physicochemical behavior, stability in chemical environments, and analytical comparison across analogs.
3. Analytical Reference and Standards
Ac-D-Asn-OH is also used to support analytical method development and reference material preparation for peptide-related workflows, including LC-MS characterization of peptide fragments and synthetic intermediates. Analytical chemists and peptide characterization labs value N-acetylated D-asparagine because it provides a defined, non-interconverting residue identity and a predictable fragmentation signature relative to uncapped or differently protected analogs. In practice, it can be used as a component standard when verifying retention behavior, monitoring coupling outcomes in synthesis development, or calibrating quantitation strategies that require a defined peptide-like analyte with an asparagine side-chain amide.
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