Ac-DL-Phg-OH is an acetylated, racemic (DL) phenylglycine derivative featuring a substituted benzyl side chain (Phg) and an acetylated amino terminus (Ac) with a free carboxylic acid (OH). The molecule contains an amide linkage from the acetyl group, a carboxylic acid functional group for salt formation or coupling chemistry, and stereochemistry is present as a DL mixture without specification of individual enantiomers. It is used as a defined amino-acid building block or peptide intermediate in peptide synthesis and structure-activity studies where phenylglycine residues and an N-acetyl protecting/activation state are required for controlled chemoselectivity and downstream derivatization.
CAT No: CP26437
CAS No:15962-46-6
Synonyms/Alias:(Acetylamino)(phenyl)aceticacid;15962-46-6;AC-DL-PHG-OH;2-(acetylamino)-2-phenylaceticacid;acetamido(phenyl)aceticacid;2-acetamido-2-phenylaceticacid;VKDFZMMOLPIWQQ-UHFFFAOYSA-N;Benzeneaceticacid,a-(acetylamino)-;AG-927/13304748;N-Acetyl-L-phenylglycine;AC1Q1KFF;AC1Q5SDL;n-acetyl-2-phenylglycine;Maybridge1_002435;AC1L3AJ5;Oprea1_138853;N-Acetyl-DL-2-phenylglycine;ACETYL-DL-PHENYLGLYCINE;DivK1c_001187;SCHEMBL3376625;alpha-acetylaminophenylaceticacid;CTK7I4221;HMS548G15;N-ACETYL-DL-PHENYLGLYCINE;(1)-(Acetamido)phenylaceticacid
Ac-DL-Phg-OH is an acetylated, racemic (DL) phenylglycine derivative supplied as a free carboxylic acid building block for peptide and peptidomimetic synthesis. With an N-acetylated amino terminus and a benzyl-like side chain typical of phenylglycine, it is frequently used as a defined structural unit in solution-phase or solid-supported assembly workflows where an unprotected N-terminus is not required. The DL stereochemistry enables access to mixed stereochemical outcomes for SAR studies, conformational exploration, and intermediate preparation where stereochemical purity is not the primary constraint.
1. Peptidomimetic Building Blocks
Ac-DL-Phg-OH is used as a phenylglycine-containing building block in peptidomimetic and modified peptide construction, particularly when an N-acetylated residue is desired to control terminal reactivity and mimic common capping patterns found in bioactive peptide scaffolds. Researchers in medicinal chemistry and chemical biology commonly incorporate this defined residue into short oligomers, fragment libraries, and SAR analog series to probe how phenylglycine substitution and N-terminal capping influence structure and downstream chemical behavior during purification and derivatization. The racemic DL configuration supports exploratory synthesis campaigns where stereochemical effects are evaluated by comparing analogs rather than relying on a single stereoisomer from the outset.
2. Solution-Phase Peptide Assembly
Ac-DL-Phg-OH serves as a practical amino acid derivative for solution-phase peptide synthesis and segment coupling strategies where an acetylated amino terminus reduces the need for additional N-protection handling. Custom peptide synthesis groups and process-development chemists use this building block to prepare defined intermediates and longer peptide segments that incorporate phenylglycine motifs, including analogs used for library generation and chemical probe development. Because the molecule is supplied as a discrete, capped residue with a free carboxylic acid, it can be integrated into common coupling workflows to build up target sequences with consistent residue identity and terminal functionality.
3. Pharmaceutical Intermediate Development
Ac-DL-Phg-OH is also used as a pharmaceutical intermediate building block for manufacturing-scale preparation of phenylglycine-containing fragments and protected or activated derivatives used downstream in medicinal chemistry programs. Process chemists and intermediate developers employ this material to standardize the incorporation of a phenylglycine unit with an N-acetylated terminus, supporting reproducible intermediate profiles for subsequent transformations and final assembly steps. The DL stereochemical form is particularly useful during early-stage route development and analog screening, where the ability to access stereochemical diversity without additional resolution steps can streamline synthesis planning.
4. SAR Library Synthesis
Ac-DL-Phg-OH is frequently selected for SAR library synthesis in peptidomimetic and peptide-analog discovery, where phenylglycine residues are used to tune sterics, aromatic character, and local conformational preferences within a scaffold. Research groups building focused analog sets use the racemic DL form to generate stereochemically mixed variants efficiently, enabling side-by-side comparison of structural hypotheses while stereochemical refinement can be pursued later if warranted by biological or physicochemical readouts. The acetylated N-terminus further supports consistent handling across library members by minimizing variability associated with terminal protection and reactivity during parallel synthesis and purification workflows.
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