Fmoc-2-Abz-OH is an Fmoc-protected amino acid derivative featuring a 2-aminobenzoic acid (2-Abz) aromatic side chain attached to the α-amino acid backbone, with the molecule bearing both an amino functionality and a carboxylic acid group in its protected form. The N-terminus is masked by an Fmoc (9H-fluorenylmethoxycarbonyl) protecting group, which controls chemoselectivity by reducing undesired reactions of the amino group during peptide-building steps, while the aromatic ring provides a benzene-based side chain suitable for π-π and hydrophobic interactions in structure-activity studies. Fmoc-2-Abz-OH is used as a protected building block for amino acid and peptide synthesis, including solid-phase peptide synthesis workflows, and it can serve as an intermediate for preparing more complex aromatic amino acid derivatives and labeled or conjugatable analogues.
CAT No: CP25380
CAS No:150256-42-1
Synonyms/Alias:Fmoc-2-Abz-OH;150256-42-1;N-Fmoc-anthranilicacid;2-(Fmoc-amino)benzoicacid;2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)benzoicacid;FMOC-2-AMINOBENZOICACID;ST50989896;Maybridge4_001966;2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}benzoicacid;2-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]benzoicAcid;Bio4A5;FMOC-ABZ-OH;AC1LJQS0;FMOC-ANTHRANILICACID;Oprea1_661448;SCHEMBL119223;446033_ALDRICH;CHEMBL524172;MolPort-002-345-375;HMS1526J08;ZINC622112;2-N-FMOC-AMINOBENZOICACID;4648AD;AKOS009156751;AB05317
Chemical Name:N-2-(9-Fluorenylmethyloxycarbonyl)amino-benzoic acid
Fmoc-2-Abz-OH is an Fmoc-protected amino acid derivative bearing the 2-aminobenzoic acid (2-Abz) aromatic side chain, with a stereogenic center absent due to the benzoic acid framework. The molecule contains a fluorenylmethoxycarbonyl (Fmoc) carbamate on the amino function, a free carboxylic acid (-CO2H), and an ortho-aminobenzoate aromatic system that can participate in π-stacking and electrophilic aromatic substitution under appropriate conditions. The Fmoc group provides orthogonal protection compatible with standard peptide synthesis cycles, while the unprotected acid enables controlled C-terminal activation and coupling or conversion to amide and ester derivatives. The aromatic 2-Abz motif is frequently used as a constrained, spectroscopically informative residue in peptide and peptidomimetic designs, making Fmoc-2-Abz-OH a practical chiral-independent building block for fragment assembly and downstream functionalization.
1. Peptide Synthesis
Fmoc-2-Abz-OH is applied in solid-phase peptide synthesis and related automated coupling workflows where the Fmoc-protected amine enables iterative N-terminal deprotection and re-coupling. The compound's free carboxylic acid supports formation of peptide bonds at the 2-Abz residue position, while the aromatic ortho-aminobenzoic acid side chain remains chemically stable under typical Fmoc removal conditions. The benzoic acid functionality can be activated to generate amide linkages, supporting incorporation into peptides for sequence-defined studies and synthetic library construction. Fmoc-2-Abz-OH thus functions as a peptide building block that integrates aromatic recognition elements into peptide backbones for structure-defined molecular scaffolds.
2. Peptidomimetics And SAR Studies
Fmoc-2-Abz-OH is used in peptidomimetic construction and structure-activity relationship studies where the 2-Abz aromatic ring provides a rigid, planar substituent for tuning binding interactions and conformational preferences. The Fmoc-protected nitrogen allows controlled placement of the aromatic residue within analogs, and the free carboxylic acid enables diversification into amides, esters, or conjugation handles that modulate polarity and hydrogen-bonding patterns. Aromatic side-chain electronics can influence intramolecular interactions and can be leveraged to compare analog series across matched scaffolds. Fmoc-2-Abz-OH therefore supports medicinal chemistry-style SAR workflows focused on residue-level substitution and functional group mapping in peptide-like systems.
3. Chemical Biology Labeling
Fmoc-2-Abz-OH is suitable for chemical biology research requiring aromatic amino acid incorporation into biorecognition probes, affinity tags, or imaging-compatible peptide constructs. The Fmoc group provides a protected handle for stepwise assembly, while the 2-Abz aromatic moiety can serve as a spectroscopic reporter or as a platform for further derivatization through carboxyl activation and amide formation. The free carboxylic acid can be converted into linkers for conjugation to polymers, surfaces, or biomolecular carriers, enabling controlled attachment points for downstream labeling strategies. Fmoc-2-Abz-OH can be employed to generate residue-defined conjugates that maintain synthetic traceability through the aromatic 2-Abz motif.
4. Side-Chain Functionalization
Fmoc-2-Abz-OH is applied in amino acid derivatization workflows where the ortho-aminobenzoic acid framework enables targeted functional transformations beyond peptide bond formation. The free carboxylic acid can be activated for esterification or amidation, allowing installation of solubilizing groups, affinity moieties, or orthogonal handles for subsequent coupling chemistry. The aromatic system may also be used as a platform for electrophilic aromatic substitution or for building heteroaryl derivatives after appropriate functional group management, while the Fmoc protection can be removed when a free amine is required for further elaboration. Fmoc-2-Abz-OH thus serves as a chemically tractable amino acid-based intermediate for side-chain engineering and downstream scaffold diversification.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-2-Abz-OH is relevant to pharmaceutical manufacturing and fine chemical synthesis routes that require reproducible protected amino acid inputs for peptide intermediate preparation. The Fmoc carbamate provides a robust protection strategy for the amino functionality during handling and coupling, while the free carboxylic acid supports conversion to activated intermediates used in peptide fragment assembly. The aromatic 2-Abz residue can be incorporated into defined intermediate peptides for subsequent processing steps such as purification, fragment coupling, and final deprotection sequences. Fmoc-2-Abz-OH can be employed as a process-compatible chiral-independent building block in industrial peptide synthesis where residue-level control and functional group orthogonality are required.
6. Analytical Research Standards
Fmoc-2-Abz-OH is used in analytical research and method development where defined aromatic amino acid residues help generate reference compounds for LC-MS, HPLC, and MS/MS identification of peptide fragments. The Fmoc-protected form enables controlled stability during sample preparation, while the free carboxylic acid allows derivatization into standards that mimic expected peptide termini or internal residues. The 2-Abz aromatic motif provides characteristic fragmentation patterns and retention behavior that can assist in validating peptide assembly and monitoring coupling outcomes. Fmoc-2-Abz-OH therefore supports analytical standard development and residue-specific verification in amino acid and peptide chemistry workflows.
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