FA-Phe-OH is a phenylalanine derivative featuring an FA (formyl/fluorophore-associated) substituent attached to the amino acid framework while retaining the core phenylalanine side chain. The molecule contains a free carboxylic acid (-COOH) and an amino functionality (-NH2 or an amino-derived form) on the alpha-carbon, with the aromatic benzyl side chain providing a hydrophobic, pi-stacking-capable group that can influence peptide or conjugate properties. FA-Phe-OH is used as a building block or labeling reagent in peptide-related synthesis and chemical biology workflows where an amino acid handle bearing an additional FA-associated moiety is required for conjugation, analytical detection, or preparation of further amino acid and peptide derivatives.
CAT No: CP27384
CAS No:71115-83-8
Synonyms/Alias:71115-83-8;4950-66-7;FA-Phe;Des-GlyGlyFAPGG;N-(3-phenylalanine;FA-PHE-OH;AC1LEM5E;ZINC57324;MFCD00063388;3-(2-Furyl)acryloyl-L-phenylalanine;N-(3-(2-Furyl)acryloyl)phenylalanine;AM024375;FT-0698880;N-[(E)-3-(2-Furyl)acryloyl]-L-Phe-OH;L-Phenylalanine,N-(3-(2-furanyl)-1-oxo-2-propenyl)-,(E)-;(2S)-2-[[(E)-3-(furan-2-yl)prop-2-enoyl]amino]-3-phenylpropanoicacid;(2S)-2-[(2E)-3-(FURAN-2-YL)PROP-2-ENAMIDO]-3-PHENYLPROPANOICACID
FA-Phe-OH is a formylated phenylalanine derivative in which the phenylalanine stereocenter is retained as a chiral amino acid framework bearing a free carboxylic acid (OH) and an N-formyl (FA) protecting group. The molecule combines an aromatic benzyl side chain with a protected amino functionality, giving a controlled reactivity profile that supports peptide coupling while limiting undesired amide formation at the nitrogen. The N-formyl group behaves as an acid-stable, base-tolerant protecting strategy in many synthetic sequences and can be removed under conditions compatible with peptide-grade intermediates, enabling downstream conversion to the corresponding unprotected amino acid. FA-Phe-OH therefore functions as a chiral amino acid intermediate and peptide building block precursor for constructing phenylalanine-containing sequences, as well as for generating derivatized aromatic side-chain analogs.
1. Peptide Coupling Chemistry
FA-Phe-OH is applied in peptide synthesis workflows where a protected amino acid with a free C-terminal carboxyl group is required for controlled amide bond formation. The N-formyl protection suppresses nucleophilicity of the amino nitrogen during coupling steps, while the carboxylic acid can participate in standard peptide coupling chemistry to generate phenylalanine residues within protected peptide chains. The aromatic side chain enables incorporation into peptide scaffolds used for studying aromatic packing, hydrophobic interactions, and backbone conformational preferences in sequence-defined peptides. FA-Phe-OH can be used as a phenylalanine building block precursor for preparing peptide intermediates that later undergo N-deprotection to support iterative chain elongation and sequence assembly in synthetic organic chemistry.
2. Protected Amino Acid Synthesis
FA-Phe-OH is suitable for protected amino acid chemistry and chiral intermediate preparation where N-protection strategies must coexist with a reactive carboxyl functionality. The N-formyl group provides a defined protecting-group handle that can be carried through coupling and functionalization steps, while the free carboxylic acid enables conversion to activated esters or other peptide-ready forms during manufacturing route design. The preserved stereochemistry at the α-carbon supports stereochemically consistent incorporation into peptides and peptidomimetic scaffolds, which is critical for maintaining side-chain orientation and backbone stereoelectronics. FA-Phe-OH can also serve as a biochemical research intermediate for generating phenylalanine-derived derivatives used in method development for amino acid protection/deprotection and downstream peptide building block preparation.
3. Side-Chain Functionalization
FA-Phe-OH is used in side-chain functionalization and aromatic derivatization programs where the phenylalanine benzyl side chain serves as a platform for further chemical modification. The N-formyl protection helps maintain chemoselectivity by reducing competing reactions at the amino group during electrophilic aromatic substitutions, side-chain oxidation/reduction strategies, or linker installation approaches that target the benzyl moiety. The free carboxylic acid can be transformed into coupling-ready intermediates after side-chain modification, enabling construction of functionalized phenylalanine analogs for peptide analog libraries. FA-Phe-OH thus supports downstream synthesis of aromatic amino acid derivatives used in structure-activity relationship studies, molecular recognition probes, and synthetic scaffolds requiring controlled stereochemistry and orthogonal functional group management.
4. Chemical Biology Probes
FA-Phe-OH is applied in chemical biology research for constructing phenylalanine-containing probes and tagged intermediates where controlled N-protection and a reactive carboxyl group enable sequential functionalization. The N-formyl group can be used to regulate amide formation during probe assembly, while the carboxylic acid supports conjugation strategies to linkers, affinity handles, or reporter moieties after appropriate activation. The benzyl aromatic side chain contributes to hydrophobic and π-interaction patterns that can influence binding behavior of peptide-like constructs used in target engagement studies or biomolecular interaction mapping. FA-Phe-OH can be incorporated into probe synthesis pipelines that require stereochemically defined amino acid building blocks and reliable functional group compatibility for downstream conjugate generation.
5. Pharmaceutical Intermediate Preparation
FA-Phe-OH is relevant to pharmaceutical intermediate preparation and fine chemical synthesis where chiral amino acid derivatives are manufactured as controlled building blocks for peptide-like active ingredients or process intermediates. The combination of an N-formyl protected amine and a free carboxylic acid supports intermediate staging, allowing conversion to activated derivatives for subsequent coupling steps while maintaining a defined protection state for the nitrogen. The aromatic phenylalanine side chain provides a common motif in peptide therapeutics and peptidomimetic chemistries, making FA-Phe-OH a practical chiral intermediate for producing phenylalanine-containing fragments used in synthetic route development. FA-Phe-OH can be employed in process chemistry contexts that require stereochemical integrity, protection-group compatibility, and manufacturable intermediate design for downstream scaffold elaboration.
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