Acetyl-D-homoPhenylalanine is an acetylated, non-proteinogenic amino acid derivative featuring a D-configured amino acid backbone with an extended "homo" phenylalanine side chain and a phenyl ring. The molecule bears an N-acetylated amino group and a carboxyl functional group, with the side chain presenting a hydrophobic aromatic moiety that can participate in π-π and van der Waals interactions during peptide or binding studies. As a chemically modified building block, it is used in peptide synthesis and structure-activity or chemical biology experiments where an N-acetylated, D-homo-phenylalanine residue and the altered side-chain length are used to probe conformational effects, labeling strategies, or the properties of synthetic peptide analogues.
CAT No: CP17404
CAS No:63393-59-9
Synonyms/Alias:hydrochloricacid;hydrogenchloride;Muriaticacid;7647-01-0;Chlorohydricacid;Acidechlorhydrique;chlorane;Chlorwasserstoff;Spiritsofsalt;Hydrogenchloride(HCl);Anhydroushydrochloricacid;Hydrochloricacidgas;Chloorwaterstof;Chlorowodor;Aqueoushydrogenchloride;Marineacid;(36cl)hydrogenchloride;Acidocloridrico;BowlCleaner;Spiritofsalt;chlorured'hydrogene;4-DBowlSanitizer;Chlorowodor[Polish];EmulsionBowlCleaner;CaswellNo.486
Acetyl-D-homoPhenylalanine is a D-configured, non-proteinogenic amino acid derivative in which the amino group is acetylated, and the side chain corresponds to a homo-extended phenylalanine motif. This N-acetylated, chiral building block is commonly used when researchers need a protected amino acid unit to control reactivity during peptide assembly or to introduce a D-stereocenter and an extended hydrophobic side chain into synthetic sequences. Its derivative form supports downstream coupling workflows while providing a defined, non-free amino functionality for controlled incorporation into larger structures.
1. Peptide Building Block Use
Acetyl-D-homoPhenylalanine is used in custom peptide synthesis workflows where a D-configured, hydrophobic homo-phenylalanine residue is required to probe stereochemical effects, conformational preferences, or proteolytic stability trends in synthetic peptides. The N-acetyl protection pattern helps define the amino functionality so that the residue can be handled as a discrete, characterized unit during sequence assembly, supporting reproducible preparation of peptide analogs used in chemical biology and protein-structure studies. Researchers often select this derivative when they want the extended phenyl side chain (relative to phenylalanine) to tune hydrophobic packing and aromatic interactions within peptide constructs.
2. Peptidomimetic SAR Intermediates
Acetyl-D-homoPhenylalanine serves as a practical intermediate for peptidomimetic development and structure-activity relationship (SAR) studies, particularly when medicinal chemistry teams need a stereochemically defined amino acid fragment bearing an acetylated amino terminus. The combination of D-configuration and the homo-phenylalanine side chain length supports the systematic evaluation of how stereochemistry and aromatic spacing influence binding-site complementarity in synthetic ligand scaffolds and peptidomimetic series. Because it is supplied as a derivative rather than a free amino acid, it is typically used to streamline assembly of analog libraries where consistent building-block identity is critical for downstream purification and characterization.
3. Analytical Reference Standards
Acetyl-D-homoPhenylalanine is also used in analytical method development and reference preparation for workflows that require defined standards of amino acid derivatives, including LC-based quantification of synthetic intermediates or peptide-related fragments. Laboratories preparing calibration materials for monitoring incorporation of D-amino acid residues or tracking derivative stability during synthesis and purification often rely on N-acetylated building blocks to match the chemical form present in the sample matrix. This makes the compound useful for verifying identity and supporting method robustness when derivative-specific detection is needed rather than relying on free amino acid standards.
4. Stereochemical Control Studies
Acetyl-D-homoPhenylalanine is frequently selected for stereochemical control experiments in which D-amino acid incorporation is used to generate defined stereochemical outcomes in synthetic peptides and related oligomers. The derivative form, with the acetylated amino group, provides a consistent starting unit that helps researchers compare sequences differing in stereochemistry or side-chain length while minimizing variability introduced by handling free amino groups. Such studies are commonly used in structure-function investigations where researchers want to isolate the impact of D-configuration and the extended aromatic side chain on folding propensity, aggregation behavior, or interaction patterns in model peptide systems.
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