Fmoc-4-Abz-OH

Fmoc-4-Abz-OH is an Fmoc-protected amino acid derivative featuring a chiral-free aromatic side chain derived from 4-aminobenzoic acid (4-Abz) and a carboxylic acid functionality suitable for peptide coupling chemistry. The molecule contains an N-(9H-fluoren-9-ylmethoxycarbonyl) protecting group that stabilizes the amino functionality during solid-phase or solution-phase assembly, while the benzoic acid moiety provides an additional, chemically addressable carboxyl group for downstream derivatization. Aromatic conjugation and the presence of two carbonyl-containing functional groups influence solubility, coupling behavior, and orthogonal reactivity relative to aliphatic amino acid building blocks. The Fmoc carbamate and terminal acid together make Fmoc-4-Abz-OH a practical chiral-independent scaffold for incorporating an aryl carboxylate motif into peptides and peptidomimetics, as well as for preparing functional intermediates in synthetic organic chemistry.

1. Peptide Synthesis

Fmoc-4-Abz-OH is applied in peptide building block preparation for solid-phase peptide synthesis and solution-phase coupling, where the Fmoc carbamate protects the aniline-derived amino group from premature acylation. The aromatic 4-aminobenzoic acid framework and terminal carboxylic acid enable incorporation of a benzoyl-like side-chain motif that can participate in hydrogen-bonding and aromatic stacking within peptide sequences. Fmoc deprotection strategies generate a reactive amine for standard peptide coupling, while the side-chain carboxyl group can be left protected or converted to an activated derivative depending on sequence design. Downstream, peptide analogs containing the 4-Abz motif can be used as research-grade scaffolds for studying sequence-dependent conformations and functional group placement in biomolecular recognition.

2. Peptidomimetics And SAR

Fmoc-4-Abz-OH is utilized in peptidomimetic construction and structure-activity relationship studies where an aryl carboxylate side chain provides a rigid, planar element for molecular recognition tuning. The Fmoc-protected amine supports controlled stepwise assembly, while the benzoic acid group can be derivatized to modulate polarity, ionization state, and steric presentation of the side chain. Side-chain functionalization can be leveraged to generate analog series for SAR workflows, including esterification, amide formation, or conversion to activated intermediates for further conjugation. The resulting aryl-containing peptide and peptidomimetic libraries serve as chemically defined platforms for mapping how aromatic carboxylate positioning affects binding-relevant physicochemical properties.

3. Chemical Biology Conjugation

Fmoc-4-Abz-OH supports chemical biology workflows that require incorporation of a functional aromatic handle into peptides or biomolecule-reactive intermediates. The benzoic acid functionality can be transformed into activated acyl species or coupling-ready derivatives, enabling attachment to amines, hydrazides, or other nucleophiles during bioconjugation design. The Fmoc group enables orthogonal manipulation: Fmoc removal exposes the amino functionality for peptide coupling, while the side-chain carboxyl group can be selectively addressed to install labels, linkers, or affinity tags. Downstream conjugates constructed from this amino acid derivative can be used for biomolecule modification studies, affinity reagent preparation, and controlled presentation of aromatic carboxylate motifs in molecular probes.

4. Protected Amino Acid Chemistry

Fmoc-4-Abz-OH is employed as a protected amino acid derivative for orthogonal protection strategies in synthetic organic chemistry, particularly when an aromatic amino acid motif must be handled without side reactions. The Fmoc carbamate stabilizes the amino group under coupling and deprotection conditions, supporting predictable generation of the free amine for acylation steps. The additional carboxylic acid group provides a second functional handle that can be protected, activated, or converted to an ester or amide depending on the synthetic sequence and desired chemoselectivity. This combination of N-protection and a carboxyl-bearing aromatic side chain makes Fmoc-4-Abz-OH suitable for preparing peptide building block sets, intermediate fragments, and downstream derivatives that require controlled functional group timing.

5. Process Chemistry Intermediate

Fmoc-4-Abz-OH is relevant to process chemistry intermediate preparation for fine chemical synthesis where a robust, isolable protected building block simplifies manufacturing of aryl-containing peptide fragments. The Fmoc-protected amine and terminal acid allow route design that separates stages of protection, coupling, and side-chain activation, reducing the risk of uncontrolled acylation during scale-up. Aromatic stability and the defined functional group set support reproducible conversion to activated derivatives for subsequent assembly steps, aligning with industrial needs for consistent intermediate quality and predictable reactivity. Downstream use includes fabrication of peptide reagents, peptidomimetic intermediates, and chemically defined scaffolds used in research supply chains and specialty chemical production.

1. Genetic, cellular, and structural characterization of the membrane potential-dependent cell-penetrating peptide translocation pore

2. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function

3. Emu oil in combination with other active ingredients for treating skin imperfections

4. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)

5. Cell-based adhesion assays for isolation of snake venom’s integrin antagonists