Ac-Thr(Ac)-OH is an N-acetylated threonine derivative bearing an additional acetyl substituent on the threonine side chain, classifying it as a protected amino acid derivative rather than a free amino acid. The molecule contains both an N-acetyl amide functionality and a carboxylic acid group, while the side-chain hydroxyl is acetylated to form an ester, and the stereochemical configuration of the threonine center is not specified in the name. Ac-Thr(Ac)-OH is used as a chemically modified building block for preparing threonine-containing peptide and peptide-like structures, including contexts where temporary masking of the side-chain hydroxyl and controlled chemoselectivity during coupling are required.
CAT No: CP26348
CAS No:137197-06-9
Synonyms/Alias:Acetyl-O-acetyl-L-threonine;137197-06-9;AC1ODW4P;SCHEMBL8847352;CTK8E5616;ZINC2575102;AKOS025294429;RT-011185;(2S,3R)-2-acetamido-3-acetyloxybutanoicacid
Ac-Thr(Ac)-OH is an acetylated threonine derivative in which the amino group is acetylated (Ac-) and the threonine side-chain hydroxyl is also acetylated, giving a protected, more hydrophobic building block compared with free threonine. This di-acetylated amino acid derivative is commonly used as a chemically defined intermediate for peptide-related synthesis and for preparing acetylated standards where controlled protection of both the α-amino and side-chain alcohol is required.
1. Peptide Segment Intermediate
Ac-Thr(Ac)-OH is used as a protected threonine building block in peptide and peptide-like intermediate workflows where both the N-terminus and the side-chain hydroxyl need to be masked to prevent undesired side reactions during coupling and assembly. Researchers in custom peptide manufacturing and medicinal chemistry synthesis often select this acetyl-protected form to maintain threonine's side-chain functionality in a protected state through segment preparation, then proceed to downstream deprotection or further functionalization according to the specific synthetic plan.
2. Acetylated Residue Standards
Ac-Thr(Ac)-OH is frequently employed as a chemically defined reference material for analytical method development and validation involving acetylated amino acid residues. Analytical chemists use this compound to support LC-MS characterization, retention-time benchmarking, and calibration/qualification strategies for workflows that distinguish acetylated versus non-acetylated threonine species, including studies of derivatization efficiency and identity confirmation in peptide and amino acid analyses.
3. Protecting-Group Controlled Derivatization
Ac-Thr(Ac)-OH serves as a controlled substrate for derivatization strategies that require threonine's reactive sites to be pre-blocked. In chemical biology and materials-adjacent research, the dual acetyl protection helps standardize reactivity during downstream transformations, enabling reproducible preparation of acetylated threonine-containing motifs, short peptide fragments, or labeled/modified analogs where side-chain hydroxyl participation must be suppressed until the intended later stage.
4. Pharmaceutical Intermediate Development
Ac-Thr(Ac)-OH is used in the development of small-molecule and peptidomimetic intermediates that incorporate acetyl-protected threonine units. Process and R&D chemists value this form as a stable, well-defined amino acid derivative for stepwise construction of more complex intermediates, particularly when the synthetic sequence benefits from temporarily masking both the α-amino group and the threonine hydroxyl to improve handling and reduce side reactions during intermediate isolation and purification.
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