Ac-DL-Pra-OEt is an amino acid derivative featuring an acetylated amino terminus (Ac-), a DL (racemic) 2-amino acid backbone, and an OEt esterified carboxyl group (OEt), where "Pra" denotes the corresponding side-chain structure of the amino acid residue. The molecule contains an acetamide linkage at the former amino position and an ester functionality at the carboxyl terminus, with the DL designation indicating a mixture of stereoisomers rather than a single defined configuration. Ac-DL-Pra-OEt is used as a protected/derivatized building block in peptide and amino acid chemistry workflows, including preparation of more complex amino acid derivatives and intermediates where masked amino and carboxyl functionalities support controlled stepwise coupling and subsequent deprotection or transformation.
CAT No: CP26830
CAS No:23235-05-4
Synonyms/Alias:Ac-dl-pra-oet;23235-05-4;ethyl2-acetamidopent-4-ynoate;SCHEMBL1071728;6082AH;AKOS006274725;AM020617;KB-47035;OR028883;FT-0695711;2-(acetylamino)-4-pentynoicacidethylester;K-6396;4-Pentynoicacid,2-(acetylamino)-,ethylester;3B3-068480
Ac-DL-Pra-OEt is an N-acetylated, racemic amino acid ester derivative featuring a protected carboxylate as an ethyl ester and an acetylated amino terminus, which suppresses free amine reactivity and improves handling in synthetic workflows. The side chain corresponds to the proline-like "Pra" residue, making this compound a useful intermediate where controlled reactivity and ester stability are required for downstream transformations. Because the material is provided as a DL mixture, it is commonly selected for reaction development, library synthesis, and analytical method work where stereochemical purity is not the primary requirement.
1. Pharmaceutical Intermediate Synthesis
Ac-DL-Pra-OEt is frequently used as a building block in the preparation of amino-acid-derived pharmaceutical intermediates, where an ester-protected carboxylate and N-acetyl protection help direct subsequent functional group manipulations. Process and medicinal chemistry teams often choose this derivative to streamline multi-step sequences that require temporary masking of both the amino functionality and the carboxyl group, enabling coupling, derivatization, or conversion to more reactive intermediates under controlled conditions. The racemic (DL) form is particularly common in early-stage route scouting and intermediate library generation, where stereochemical resolution can be deferred to later stages if needed.
2. Peptide-Adjacent Derivative Building
Ac-DL-Pra-OEt is applied in peptide-adjacent synthesis programs that require a proline-like residue surrogate with reduced risk of side reactions from a free amino group. Researchers in custom peptide manufacturing development and process chemistry use N-acetylated amino acid esters to assemble or modify protected fragments that can later be converted into coupling-ready forms, supporting the preparation of dipeptide-like scaffolds, constrained amide linkages, or backbone-modified analogs. The ethyl ester functionality provides a practical handle for controlled activation or transformation during downstream steps, while the DL composition supports rapid exploratory synthesis without introducing stereochemical complexity at the intermediate stage.
3. Reaction Development And Screening
Ac-DL-Pra-OEt is routinely used as a standard substrate for reaction optimization and small-scale screening in organic synthesis laboratories, especially when the goal is to evaluate reactivity trends across protected amino acid derivatives. Its dual protection pattern (acetylated nitrogen and esterified carboxyl) reduces variability associated with competing acid/base or nucleophilic behaviors, making it a convenient reference material for comparing coupling efficiency, derivatization outcomes, or purification performance across candidate reagents and conditions. Because the compound is supplied as a DL mixture, it is also well-suited to screening workflows where stereochemical assignment is not required to interpret conversion, yield, or impurity profiles at the development stage.
4. Analytical Method Development
Ac-DL-Pra-OEt is used in analytical chemistry workflows as an amino acid ester reference material for method development and validation of LC-based assays that quantify protected amino acid derivatives. Analytical groups leverage its defined protection pattern to develop chromatographic conditions that separate ester and amide-containing species, monitor conversion during intermediate synthesis, and establish retention-time behavior for structurally related substrates. The racemic nature can be advantageous for method robustness when the analytical objective is to track total compound levels rather than enantiomer-specific distributions.
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