Boc-D-4Pal-OH is a protected amino acid derivative featuring a tert-butoxycarbonyl (Boc) carbamate protecting group on the amino functionality and a D-configured 4-palmitoylphenylalanine side chain (4Pal) connected to the α-amino and α-carboxyl framework. The molecule contains both an α-carboxylic acid (-COOH) and a Boc-protected nitrogen, while the aromatic side chain bears a long-chain palmitoyl substituent that provides pronounced hydrophobic character and a handle for amphiphilic or membrane-mimetic design in peptide-related materials. As a stepwise synthesis intermediate, it is used in controlled peptide assembly workflows where the Boc group helps suppress undesired amide formation at the amino terminus until deprotection, supporting the incorporation of the 4Pal residue into peptides and peptide conjugates for structure-activity studies and materials research.
CAT No: CP25814
CAS No:37535-58-3
Synonyms/Alias:37535-58-3;BOC-D-4-PYRIDYLALANINE;(R)-2-((tert-Butoxycarbonyl)amino)-3-(pyridin-4-yl)propanoicacid;Boc-3-(4-pyridyl)-D-Ala-OH;BOC-D-4-PYRIDYLALA;Boc-3-(4-pyridyl)-D-alanine;Boc-D-3-(4-pyridyl)-alanine;Boc-beta-(4-pyridyl)-D-Ala-OH;SBB065301;(R)-2-Tert-Butoxycarbonylamino-3-Pyridin-4-Yl-PropionicAcid;(2R)-2-[(tert-butoxy)carbonylamino]-3-(4-pyridyl)propanoicacid;3-Pyridin-4-yl-D-alanine,N-BOCprotected;AC1Q1MTW;BOC-D-4PAL-OH;AC1MC1A9;15030_ALDRICH;BOC-4'-PYRIDYL-D-ALA;SCHEMBL3338649;BOC-D-4-PYRIDINEALANINE;BOC-D-ALA(4-PYRI)-OH;15030_FLUKA;FNYWDMKESUACOU-SNVBAGLBSA-N;MolPort-001-758-705;BOC-D-ALA(4'-PYRIDYL)-OH;N-Boc-beta-(4-pyridyl)-D-alanine
Chemical Name:N-alpha-t-Butyloxycarbonyl-3-(4-pyridine)-D-alanine
Boc-D-4Pal-OH is a Boc-protected D-4-pyridylalanine derivative in which the amino group is masked as a tert-butoxycarbonyl (Boc) carbamate while the side chain retains a pyridine aromatic functionality. This stereochemically defined amino acid building block is commonly used to introduce a D-configured 4-pyridylalanine residue into protected amino acid segments for peptide and peptidomimetic synthesis. The pyridine side chain provides a chemically addressable heteroaromatic motif that is frequently leveraged for downstream coordination, physicochemical tuning, and analytical handle development in synthetic workflows.
1. Peptide Segment Building
Boc-D-4Pal-OH is used as a protected amino acid building block for assembling D-4-pyridylalanine-containing peptides via standard peptide coupling workflows in custom peptide synthesis. The Boc protection enables controlled N-terminal chemistry during segment condensation and library construction, while the D stereochemistry supports incorporation of stereodefined residues for structure-activity relationship studies and conformational profiling. Researchers selecting this building block often aim to embed the 4-pyridyl side chain to modulate local polarity and introduce a heteroaromatic feature that can influence peptide behavior in solution and during subsequent derivatization.
2. Peptidomimetic Medicinal Chemistry
Boc-D-4Pal-OH supports medicinal chemistry programs that develop peptidomimetics and constrained peptide analogs where heteroaromatic side chains are used to tune binding-site interactions and physicochemical properties. The Boc-protected amino functionality makes it practical for incorporation into multi-step synthetic sequences that generate peptide-like scaffolds, while the pyridine ring offers a chemically distinct motif for later functional elaboration or for establishing defined electronic and hydrogen-bonding characteristics within the analog. Medicinal chemistry groups frequently use stereodefined D-amino acid residues to explore how backbone stereochemistry impacts target engagement patterns and structure-property relationships during lead optimization.
3. Coordination-Enabled Derivatization
Boc-D-4Pal-OH is leveraged in synthetic chemistry and chemical biology workflows that use pyridine-containing residues as coordination sites for metal-assisted assembly or post-synthetic modification strategies. After incorporation into a peptide or peptidomimetic intermediate, the 4-pyridyl side chain can serve as a localized ligand for constructing defined metal-ligand architectures, enabling materials-oriented conjugation schemes and controlled organization of biomolecular fragments. Teams developing functional peptide conjugates or metal-responsive chemical probes often prefer this Boc-protected D-4-pyridylalanine building block because it combines stereochemical control at the amino acid level with a persistent heteroaromatic handle that remains available for downstream coordination chemistry.
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