Fmoc-3,5-dinitro-Tyr-OH is a protected tyrosine derivative in which the α-amino group is protected by an Fmoc (9-fluorenylmethoxycarbonyl) group and the side chain is a phenolic ring bearing two nitro substituents at the 3- and 5-positions. The molecule contains both an Fmoc-protected amino functionality and a free carboxylic acid (-COOH), while the nitro-activated phenol provides a substituted phenolic side chain with electron-withdrawing character. It is used as a stepwise peptide-synthesis building block or intermediate, where the protected α-amino group supports controlled coupling and the dinitrophenyl side chain can be used for structure-activity studies, analytical derivatization, or chemical labeling based on its distinctive aromatic functionality.
CAT No: CP26598
CAS No:195434-42-5
Synonyms/Alias:Fmoc-3,5-dinitro-L-tyrosine;Fmoc-3,5-dinitro-Tyr-OH;195434-42-5;SCHEMBL8697104;CTK8E5921;C24H19N3O9;ZINC2392279;6760AH;RT-012867
Fmoc-3,5-dinitro-Tyr-OH is an Fmoc-protected tyrosine derivative bearing a phenolic side chain substituted with two nitro groups at the 3- and 5-positions. The molecule combines a chiral amino acid core with an N-(9H-fluoren-9-ylmethoxycarbonyl) protecting group and a free carboxylic acid, enabling controlled peptide coupling while retaining the side-chain functionality for subsequent transformation. The dinitrophenol motif introduces strong electron-withdrawing character and enables characteristic aromatic reactivity, including nucleophilic aromatic substitution and redox-sensitive behavior under appropriate conditions. The presence of both protected amine and unprotected acid makes the compound a practical chiral building block for peptide synthesis and a chemically informative intermediate for side-chain functionalization strategies.
1. Peptide Synthesis Compatibility
Fmoc-3,5-dinitro-Tyr-OH supports solid-phase peptide synthesis workflows where the Fmoc group serves as an orthogonal N-protection handle for iterative chain elongation. The tyrosine backbone provides a stereodefined alpha-amino acid unit, while the free carboxylic acid participates in standard peptide coupling chemistry to form amide linkages. The 3,5-dinitro-substituted phenol side chain can be carried through peptide assembly as a protected aromatic functionality that modulates electronics and can later be converted into other phenolic or aniline-like motifs depending on the downstream transformation plan. Incorporation of this residue into peptide sequences can be applied to synthesize nitro-functional peptide analogs for chemical biology studies and to prepare peptide materials where aromatic electronic tuning is required.
2. Amino Acid Side-Chain Functionalization
Fmoc-3,5-dinitro-Tyr-OH enables side-chain functionalization routes that leverage the activated dinitrophenol aromatic system for further derivatization. The phenolic oxygen and the electron-deficient ring bearing two nitro groups provide reactive handles for conversion into alternative aromatic functionalities, including selective reduction pathways to amine-containing derivatives or substitution-based remodeling of the ring. The Fmoc-protected amino acid format allows the compound to be processed as a stable intermediate during synthesis, followed by deprotection and side-chain conversion to generate functionalized tyrosine analogs for building peptidomimetics. Downstream use can include generation of chemically distinct peptide tags, aromatic crosslinking precursors, and research intermediates for mapping how tyrosine electronics influence molecular recognition.
3. Chemical Biology Labeling
Fmoc-3,5-dinitro-Tyr-OH can be applied in chemical biology research where nitro-activated aromatic groups serve as probes for studying labeling selectivity and microenvironment-dependent reactivity. The tyrosine scaffold provides a recognizable amino acid context for incorporation into peptides or protein fragments, while the dinitro substitution pattern introduces strong spectroscopic and reactivity signatures that can be tracked during analytical characterization. The Fmoc-protected backbone supports controlled introduction into peptide constructs, enabling site-specific placement of the dinitrophenyl motif for subsequent conjugation or transformation. The resulting labeled peptide or peptidomimetic derivatives can be used as intermediates for biomolecule modification workflows and for developing structure-defined probes for biochemical assays.
4. Peptidomimetics And SAR Studies
Fmoc-3,5-dinitro-Tyr-OH is suitable for peptidomimetic construction and structure-activity relationship studies where electronic modulation of a tyrosine-like side chain is a design variable. The chiral amino acid core allows consistent stereochemical presentation of the residue, while the dinitro-phenolic aromatic group provides a tunable electron-withdrawing substituent pattern that can influence hydrogen bonding, aromatic interactions, and local polarity in peptide analogs. The Fmoc-protected amine and free carboxylic acid enable systematic library synthesis through peptide coupling, facilitating comparative studies across analog series. Downstream derivative formation can include conversion to reduced or substituted aromatic variants, supporting SAR-driven exploration of how tyrosine side-chain electronics affect binding motifs in molecular design programs.
5. Process Chemistry Intermediate
Fmoc-3,5-dinitro-Tyr-OH functions as a defined chiral intermediate for industrial fine chemical synthesis and process chemistry development targeting nitro-functional amino acid derivatives. The Fmoc protecting group and the unprotected carboxylic acid create a controllable protection/deprotection profile that can be aligned with manufacturing steps for peptide building blocks and downstream aromatic transformations. The dinitro substitution pattern provides a stable, structurally encoded functionality that can be carried through protected-amino-acid handling before conversion to other aromatic chemotypes required for specialty chemical production. The compound's compatibility with standard peptide coupling and its role as a side-chain-bearing intermediate support scalable preparation of nitro-tagged residues and related derivatives used in research-grade manufacturing pipelines.
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