Ac-Thr-OMe is an N-acetylated threonine methyl ester amino acid derivative in which the threonine amino acid backbone is converted to a carboxylate ester (-OMe) and the α-amino group is capped with an acetyl (Ac) protecting group. The molecule retains the threonine side chain bearing a β-hydroxyl substituent, while the ester and N-acetyl functionalities modulate hydrogen-bonding and chemoselectivity compared with the corresponding free amino acid. Ac-Thr-OMe is used in peptide and amino acid chemistry as a protected/derivatized threonine building block for preparing more complex amide-linked structures and for analytical or synthetic studies involving controlled handling of the amino and carboxyl functionalities.
CAT No: CP26852
CAS No:2458-78-8
Synonyms/Alias:2458-78-8;Acetyl-L-threonineMethylester;AC-THR-OME;(2S,3R)-Methyl2-acetamido-3-hydroxybutanoate;ZINC02555097;SCHEMBL5810740;CTK4F3959;MolPort-020-004-630;N-Acetyl-L-threoninemethylester;ZINC2555097;6088AH;L-Threonine,N-acetyl-,methylester;AKOS006272410;AJ-39699;AK135277;AM030826;KB-47121;FT-0634296;ST51051487;K-6567;METHYL(2S,3R)-2-ACETAMIDO-3-HYDROXYBUTANOATE
Ac-Thr-OMe is an N-acetylated threonine methyl ester derivative, combining a protected amino terminus (acetylated) with a methyl ester at the carboxyl group. This structure makes it a compact, non-ionizable building block that is routinely handled in peptide and peptidomimetic workflows where controlled reactivity and minimized side reactions are important. The threonine side chain retains a hydroxyl group, enabling downstream functionalization or incorporation into larger sequences under conditions compatible with ester and acetamide stability.
1. Peptide Segment Building
Ac-Thr-OMe is used as a threonine-containing segment precursor for assembling short peptides and peptide-like structures in solution-phase synthesis and related segment condensation strategies. The N-acetyl group provides an amide-stabilized amino terminus, while the methyl ester form offers a defined carboxyl functionality that can be carried through intermediate steps before conversion to a coupling-ready acid or activated derivative. Researchers developing threonine-rich motifs, sequence analogs, or model substrates often select this derivative to keep the amino terminus protected and to manage reactivity during stepwise chain assembly.
2. Peptidomimetic Intermediate Preparation
Ac-Thr-OMe serves as a practical intermediate for preparing peptidomimetic scaffolds and threonine-functionalized analogs where the threonine side-chain hydroxyl needs to be preserved for later modification. Medicinal chemistry groups use this type of protected amino acid ester to build libraries of analogs that probe how threonine stereochemistry and side-chain functionality influence conformational preferences and chemical properties. The combination of an acetamide at nitrogen and an ester at the carboxyl position allows iterative derivatization of the side chain while maintaining a controlled functional-group profile for downstream elaboration.
3. Reference Substrate and Assay Modeling
Ac-Thr-OMe is frequently employed in biochemical assay development and chemical biology as a defined, threonine-based substrate mimic for evaluating reaction conditions, derivatization steps, or analytical workflows that require a known amino acid derivative with minimal ambiguity in ionization state. Because the molecule is capped at both the amino terminus and carboxyl group, it behaves as a stable analytical standard-like component in method screening, enabling reproducible handling compared with free threonine or more reactive protected forms. Laboratories performing LC-MS method development, derivatization optimization, or model substrate comparisons often use such derivatives to benchmark retention behavior and derivatization efficiency for threonine-containing analytes.
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