Acetyl-trans-4-hydroxy-L-proline is an acetylated, trans-configured derivative of the proteinogenic amino acid proline bearing a 4-hydroxy substituent, placing it in the hydroxyproline class of amino acid derivatives. The molecule contains an N-acetylated amino functionality and a carboxyl group, with the pyrrolidine ring constrained by the trans stereochemical relationship between the ring and substituent, while the 4-hydroxy side-chain provides a polar hydroxyl group capable of hydrogen bonding. As an amino acid derivative, it is used in peptide chemistry and chemical biology workflows where N-acetylation and hydroxy substitution affect conformational behavior, side-chain reactivity, and analytical characterization of proline-containing peptide building blocks.
CAT No: CP01107
CAS No:33996-33-7
Synonyms/Alias:33996-33-7;N-Acetyl-L-hydroxyproline;(2S,4R)-1-acetyl-4-hydroxypyrrolidine-2-carboxylicacid;trans-1-Acetyl-4-hydroxy-l-proline;AC-HYDROXYPROLINE;Oxaceprol;UNII-Q0XV76B96L;AC-HYP-OH;ST086508;DSSTox_CID_26410;DSSTox_RID_81589;DSSTox_GSID_46410;Jonctum;SMR000857165;CAS-33996-33-7;L-Proline,1-acetyl-4-hydroxy-,(4R)-;Oxaceprolum;Tejuntivo;N-Acetyl-trans-4-hydroxy-L-proline;NCGC00164517-01;Oxaceprol(INN);Jonctum(TN);Oxaceprolum[INN-Latin];AC1L23YH;SCHEMBL25976
Acetyl-trans-4-hydroxy-L-proline is a trans-4-hydroxy-L-proline derivative bearing an N-acetyl group, providing a protected, conformationally biased proline scaffold with a free carboxylate/acid functionality depending on the supplied form. The trans-4-hydroxy stereochemistry and secondary amide character make it a commonly used building block for peptide and peptidomimetic synthesis where reduced side reactions from the ring nitrogen are advantageous. In practice, researchers select this derivative to install a hydroxyproline motif with controlled backbone functionality for downstream coupling, analytical method development, and specialty intermediate preparation.
1. Peptidomimetic Building Block
Acetyl-trans-4-hydroxy-L-proline is frequently used as a defined amino acid building block in peptidomimetic and peptide fragment synthesis, particularly when a hydroxyproline-containing residue is required in a trans configuration. Medicinal chemistry groups and custom peptide manufacturers use this scaffold to assemble short peptides and constrained analogs that emulate hydroxyproline-rich motifs, where the proline ring and 4-hydroxy side chain contribute to conformational restriction and hydrogen-bonding patterns. The N-acetyl protection strategy helps maintain the ring nitrogen in an amide state during coupling and purification steps, supporting cleaner fragment assembly for SAR-focused workflows.
2. Hydroxyproline Motif Synthesis
Acetyl-trans-4-hydroxy-L-proline supports the preparation of hydroxyproline-containing peptide standards and synthetic intermediates used in peptide chemistry and chemical biology. Researchers in structural biology and protein chemistry often require well-defined hydroxyproline residues to generate reference peptides for mass spectrometry workflows, including method development and verification of fragmentation behavior for hydroxyproline-bearing sequences. The trans-4-hydroxy stereochemical definition is especially valuable when comparing isomeric or stereochemically distinct hydroxyproline analogs in analytical studies, where residue identity and stereochemistry can strongly influence chromatographic and MS readouts.
3. Pharmaceutical Intermediate Development
Acetyl-trans-4-hydroxy-L-proline is also used in the development of pharmaceutical intermediates and specialty small-molecule precursors that require a hydroxyproline-derived stereocenter. Process development chemists and industrial R&D teams incorporate this derivative as a controlled chiral building block when designing peptidomimetic fragments, proline-based scaffolds, or protected hydroxyproline intermediates for further functionalization. The presence of the N-acetyl group provides a stable handle that can be carried through multi-step synthesis sequences, enabling reliable downstream transformations while minimizing variability associated with unprotected amino functionality.
4. Analytical Reference Material
Acetyl-trans-4-hydroxy-L-proline is commonly selected as an analytical reference component for LC-MS and related characterization workflows involving hydroxyproline derivatives. Analytical chemistry teams use it to confirm identity, retention behavior, and mass accuracy for hydroxyproline-containing synthetic mixtures, peptide digests, or derivatization experiments where proline hydroxylated residues are expected. Because the compound is a discrete, stereochemically defined derivative with an N-acetylated nitrogen, it serves as a practical benchmark when distinguishing hydroxyproline analogs that differ in N-protection state or stereochemical configuration.
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