Ac-p-amino-Phe-OMe is an N-acetylated, para-amino substituted phenylalanine methyl ester derivative in which the aromatic side chain of phenylalanine bears an additional amino group at the para position. The molecule contains an acetylated amino terminus (Ac-), a methyl ester carboxyl group (-CO2Me), and a free para-amino substituent on the benzyl ring, providing both an aniline-like functionality and ester-protected carboxyl chemistry while the backbone nitrogen is blocked to control chemoselectivity. As a protected amino acid derivative, it is used in peptide and amide synthesis workflows and in structure-activity or labeling studies where a para-aminophenylalanine handle is required alongside an esterified carboxyl group and an N-acetyl protecting group to support stepwise assembly or downstream functionalization.
CAT No: CP27058
CAS No:36097-42-4
Synonyms/Alias:AC-P-AMINO-PHE-OME;36097-42-4;AC-p-Amino-Phen-Ome;AC1OLQO2;SCHEMBL6572925;ZINC4899419;AM029172;FT-0639297;methyl(2S)-2-acetamido-3-(4-aminophenyl)propanoate;METHYL(2S)-3-(4-AMINOPHENYL)-2-ACETAMIDOPROPANOATE
Ac-p-amino-Phe-OMe is an N-acetylated, para-amino substituted phenylalanine methyl ester derivative (Ac-protected amino group with a methyl ester at the C-terminus), combining an anilide-type aromatic amine with a protected backbone functionality. This structure is commonly handled as a peptide-like building block for preparing substituted aromatic amino acid motifs, where the para-amino group provides a direct site for further derivatization while the methyl ester and N-acetyl group support controlled downstream coupling chemistry.
1. Substituted Aromatic Peptides
Ac-p-amino-Phe-OMe is used by peptide chemistry groups to assemble short peptide segments or peptide analogs that require a para-aminophenylalanine motif. The N-acetylation and C-terminal methyl ester help maintain the building block in a defined, peptide-compatible form during stepwise assembly, while the free para-amino substituent enables post-coupling functionalization to generate diversified analog libraries for structure-activity relationship studies in chemical biology and medicinal chemistry programs.
2. Medicinal Chemistry Intermediates
Ac-p-amino-Phe-OMe serves as a practical intermediate for medicinal chemistry workflows that need access to para-aminophenylalanine-derived scaffolds. Researchers use the intact aromatic amine for downstream transformations that introduce additional substituents or enable conjugation handles, while the methyl ester and N-acetyl protection pattern supports controlled progression toward larger peptidomimetic frameworks and substituted aromatic intermediates used in lead optimization campaigns.
3. Aromatic Amine Derivatization
Ac-p-amino-Phe-OMe is frequently selected for derivatization strategies that leverage the para-amino group as a functional handle for forming new C-N or heteroatom-containing substituents. In research settings focused on generating analogs for binding studies, assay development, or chemical probe construction, the derivative's protected backbone end groups help preserve reactivity selectivity, allowing the aromatic amine to be modified without simultaneously exposing the backbone as a competing electrophile or nucleophile.
4. Peptidomimetic Building Block Synthesis
Ac-p-amino-Phe-OMe is applied in peptidomimetic and constrained-structure synthesis where a defined aromatic amino acid unit is required as a precursor. Development teams use the methyl ester form to enable subsequent conversion to other carboxylate derivatives during the build-out of larger scaffolds, while the N-acetyl group provides a stable amide terminus that supports iterative assembly toward peptide-like structures used in target engagement and chemical biology tool development.
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