Fmoc-beta-(7-methoxy-coumarin-4-yl)-Ala-OH is an Fmoc-protected alanine derivative bearing a β-substituent linked to a 7-methoxy-coumarin-4-yl fluorophore, placing it in the class of unnatural, structurally modified amino acids used for fluorescent labeling in peptide-related synthesis. The molecule contains a free carboxylic acid and an amino group masked by the Fmoc protecting group, while the coumarin substituent provides an aromatic, conjugated system; stereochemistry is not specified in the product name, so no absolute configuration is assumed. In synthesis and chemical biology workflows, this amino acid is employed as a building block for stepwise peptide assembly and as a fluorescent handle for analytical method development, structure-activity studies, and labeling experiments where a coumarin reporter is incorporated into peptide frameworks.
CAT No: CP27176
CAS No:524698-40-6
Synonyms/Alias:524698-40-6;SCHEMBL5622852;CTK1G7855;(S)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-3-(7-METHOXY-2-OXO-2H-CHROMEN-4-YL)-PROPIONICACID;ZINC33369280;N-(9H-Fluorene-9-ylmethoxycarbonyl)-3-(2-oxo-7-methoxy-2H-1-benzopyran-4-yl)-L-alanine
Fmoc-beta-(7-methoxy-coumarin-4-yl)-Ala-OH is a chiral, Fmoc-protected alanine derivative bearing a β-substituent linked to a 7-methoxy coumarin chromophore at the 4-position. The molecule contains an Fmoc carbamate on the α-amino function, a free carboxylic acid for C-terminal peptide coupling, and a conjugated aromatic lactone system that provides strong fluorescence and UV absorbance for photophysical readouts. The β-amino-acid topology and coumarin-bearing side functionality create defined steric and electronic features that can influence peptide conformation and labeling behavior. The coumarin ring can participate in photochemical and spectroscopic assays while remaining chemically stable under peptide synthesis conditions, making the compound a structurally informative amino acid building block and analytical tag precursor.
1. Peptide Synthesis
Fmoc-beta-(7-methoxy-coumarin-4-yl)-Ala-OH is used in peptide building-block workflows where the Fmoc carbamate supports standard solid-phase peptide synthesis and the free carboxylic acid enables amide bond formation at the C-terminus. The β-substituted coumarin moiety functions as a spectroscopic handle, allowing incorporation of a fluorescent reporter directly into peptide backbones or side-chain-modified analogs. The chiral alanine center provides stereochemical control for backbone assembly, while the β-substitution pattern can be leveraged to tune local conformational preferences in peptide segments. Downstream, the resulting coumarin-containing peptides can be used for structure-function studies, synthesis of labeled standards, and comparative analyses of peptide coupling or fragment assembly.
2. Chemical Biology Labeling
Fmoc-beta-(7-methoxy-coumarin-4-yl)-Ala-OH serves chemical biology applications that require site-specific fluorescent tagging of biomolecular constructs. The coumarin chromophore provides a built-in reporter for monitoring peptide uptake, binding, or trafficking in assay formats that rely on optical readout rather than additional dyes. The Fmoc-protected amino acid form supports controlled incorporation into peptide conjugates, enabling researchers to generate defined labeling positions without introducing extraneous reactive dyes. The free carboxyl group and the coumarin lactone scaffold can also facilitate downstream derivatization routes after peptide assembly, supporting the preparation of labeled probes and imaging-compatible molecular tools.
3. Peptidomimetics And SAR Studies
Fmoc-beta-(7-methoxy-coumarin-4-yl)-Ala-OH is suitable for peptidomimetic construction and structure-activity relationship studies where a constrained, fluorescently readable amino acid analog is incorporated into bioactive scaffolds. The β-coumarin substitution introduces an aromatic, electron-rich fragment that can modulate hydrophobicity, π-interactions, and steric bulk relative to native alanine, enabling SAR mapping of backbone and side-chain effects. The stereogenic α-center supports consistent chiral presentation across analog series, while the Fmoc strategy allows systematic analog synthesis with controlled sequence placement. The coumarin reporter enables parallel quantification of binding or conformational changes in comparative panels, supporting iterative optimization of peptide-like ligands and analog libraries.
4. Analytical Research Standards
Fmoc-beta-(7-methoxy-coumarin-4-yl)-Ala-OH is applied in analytical research as a chromophore-bearing amino acid intermediate for method development and calibration in fluorescence-based detection. The 7-methoxy coumarin system provides measurable absorbance and emission signals that can be exploited for monitoring peptide synthesis progress, verifying incorporation of the tagged residue, and generating reference materials for chromatographic and spectroscopic workflows. The presence of Fmoc and a carboxylic acid allows the compound to be integrated into controlled derivatization or coupling schemes that yield well-defined labeled species for instrument validation. The resulting labeled standards can support routine analytical checks in synthetic chemistry and peptide research pipelines where consistent optical response is required.
5. Process Chemistry Intermediate
Fmoc-beta-(7-methoxy-coumarin-4-yl)-Ala-OH is relevant to process chemistry and fine chemical synthesis planning because it combines a protected amino functionality with a coupling-ready carboxylic acid in a single, isolable chiral intermediate. The Fmoc carbamate provides a predictable protection state for downstream peptide coupling operations, while the coumarin chromophore remains compatible with typical peptide-manufacturing conditions that rely on orthogonal protection and stepwise deprotection. The β-substituted aromatic lactone can be used to design manufacturing routes for fluorescent peptide building blocks and labeled intermediate streams with defined structure. The compound can therefore serve as a controllable input for producing coumarin-tagged peptide fragments, research-grade conjugates, and process intermediates used in specialty chemical production.
6. Bioconjugation Building Blocks
Fmoc-beta-(7-methoxy-coumarin-4-yl)-Ala-OH is suitable for bioconjugation strategies that require incorporation of a fluorescent amino acid unit into peptide-based linkers or conjugate scaffolds. The Fmoc-protected amino group supports sequence-defined assembly before conjugation, while the free carboxylic acid enables coupling to amine-bearing partners through peptide-bond formation logic. The coumarin chromophore provides a direct optical reporter in the final conjugate, supporting monitoring of conjugation efficiency and subsequent biomolecular interactions in assay formats. The stereochemical integrity of the alanine core helps maintain structural fidelity in linker regions, enabling reproducible preparation of labeled bioconjugates used in chemical biology and biomolecule modification workflows.
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