Fmoc-4-tert-butyl-D-Phenylalanine is an Fmoc-protected, non-natural amino acid derivative in which the phenylalanine backbone bears a para-tert-butyl substituent on the aromatic side chain and a D stereochemical configuration at the alpha carbon as indicated by the name. The molecule contains an Fmoc carbamate on the amino group and a free carboxylic acid, with the bulky hydrophobic tert-butyl group modulating the side-chain sterics and aromatic character while the D configuration defines the stereochemical outcome in peptide assembly. In peptide chemistry, this protected amino acid is used as a building block for introducing the substituted phenylalanine residue into peptides via stepwise coupling strategies where the Fmoc group controls amino-group chemoselectivity during synthesis.
CAT No: CP11307
Fmoc-4-tert-butyl-D-Phenylalanine is a fluorene-based Fmoc-protected, D-configured phenylalanine derivative bearing a 4-tert-butyl substituent on the aromatic ring. The molecule combines an activated, N-Fmoc amino functionality for stepwise peptide assembly with a sterically demanding, hydrophobic side chain that can influence conformational preferences and aromatic packing in peptide and peptidomimetic scaffolds. The D stereocenter at the α-carbon provides stereochemical control for unnatural amino acid incorporation and for tuning protease stability and receptor recognition patterns. The persistent aromatic ring and tert-butyl group support downstream derivatization or serve as a durable hydrophobic handle during synthetic intermediate preparation and structure-function studies.
1. Peptide Synthesis
Fmoc-4-tert-butyl-D-Phenylalanine is used in peptide synthesis workflows where Fmoc protection enables orthogonal, base-mediated deprotection and subsequent amide bond formation at the α-amino group. The D-configuration and bulky 4-tert-butyl phenyl side chain can be incorporated as a chiral building block to modulate local sterics, hydrophobicity, and aromatic interactions within peptide sequences. The aromatic ring and tert-butyl substituent remain chemically stable under typical coupling and deprotection conditions, supporting reliable incorporation during protected amino acid chemistry. The resulting D-amino acid residues can be applied to generate peptide analogs for biochemical research intermediate preparation and for studying sequence-dependent structure and recognition.
2. Peptidomimetics And SAR
Fmoc-4-tert-butyl-D-Phenylalanine is suitable for peptidomimetic construction and structure-activity relationship studies where the D-stereocenter and nonpolar aromatic side chain provide a defined stereochemical and physicochemical motif. The 4-tert-butyl substitution on the phenyl ring introduces steric bulk that can be exploited to probe binding pocket shape complementarity and to tune hydrophobic contacts without changing the core amino acid backbone. The Fmoc group supports rapid assembly of analog libraries through repeated peptide coupling cycles, enabling systematic variation of residue context around the unnatural amino acid. The stable aromatic/tert-butyl side chain can guide downstream scaffold generation for SAR-driven molecular design and medicinal chemistry research.
3. Chemical Biology Labeling
Fmoc-4-tert-butyl-D-Phenylalanine can be applied in chemical biology research as a protected amino acid precursor for building peptide conjugates that incorporate hydrophobic aromatic segments for membrane-associated probes or binding-domain scaffolds. The Fmoc-protected amine allows controlled incorporation into peptides prior to conjugation steps, while the D-configuration can help reduce susceptibility to proteolysis in labeling reagents. The persistent aromatic ring bearing a tert-butyl group can serve as a nonreactive hydrophobic anchor during bioconjugation workflows, supporting consistent conjugate behavior during downstream purification and analytical characterization. The resulting D-containing peptide conjugates may function as biochemical research intermediates for molecular recognition studies and biomolecule modification strategies.
4. Process Chemistry Intermediate
Fmoc-4-tert-butyl-D-Phenylalanine is relevant to process chemistry and fine chemical synthesis as a chiral, protected amino acid intermediate that aligns with industrial peptide-building block manufacturing practices. The Fmoc-protected amino functionality supports standardized coupling chemistry and controlled deprotection using base, while the D stereocenter provides a defined stereochemical input for downstream stereospecific assembly. The aromatic tert-butyl side chain contributes to predictable physical handling characteristics associated with hydrophobic, nonpolar substituents, which can be advantageous when designing scalable routes for protected amino acid derivatives. The compound can be utilized as a feedstock for producing D-amino acid-containing peptide fragments and peptidomimetic intermediates used in specialty chemical production and industrial chemical manufacturing.
5. Unnatural Amino Acid Incorporation
Fmoc-4-tert-butyl-D-Phenylalanine is used for unnatural amino acid incorporation in synthetic organic chemistry and peptide science where D-amino acid stereochemistry is required to tune conformational outcomes and enzymatic stability. The α-amino group protected as Fmoc enables compatibility with common peptide coupling protocols, while the D configuration ensures stereochemical fidelity at the incorporation site. The 4-tert-butyl phenyl side chain provides a durable hydrophobic/aromatic element that can influence folding propensity and side-chain packing in peptide analogs. The resulting D-phenylalanine-containing products can serve as chiral intermediates for downstream derivatization, including generation of peptide fragments for enzyme studies, receptor-binding investigations, and stereochemically defined molecular scaffolds.
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