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Purchase from China Fmoc-D-4-Chlorophenylalanine丨CAS 142994-19-2
Fmoc-D-4-Chlorophenylalanine is a protected non-standard amino acid featuring a fluorenylmethoxycarbonyl (Fmoc) protecting group on the amino functionality and a chlorine substituent at the 4-position of the aromatic ring. Its D-configuration, Fmoc protection, and para-chlorinated phenyl side chain make it a useful building block for solid-phase peptide synthesis, medicinal chemistry, and advanced organic synthesis. The Fmoc group supports controlled amino-group protection during peptide assembly, while the modified aromatic side chain offers structural diversity for developing peptides and functional molecules.
Chemical Identifiers
| InChI | InChI=1S/C24H20ClNO4/c25-16-11-9-15(10-12-16)13-22(23(27)28)26-24(29)30-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/t22-/m1/s1 |
| InChI Key | CQPNKLNINBUUOM-JOCHJYFZSA-N |
| Smiles | C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@H](CC4=CC=C(C=C4)Cl)C(=O)O |
| EC No. | 621-077-2 |
| MDL No. | MFCD00077066 |
| PubChem CID | 16213163 |
Applications
Solid-Phase Peptide Synthesis
Fmoc-protected amino acids are widely used in solid-phase peptide synthesis (SPPS), where the Fmoc group can be selectively removed under suitable basic conditions during peptide-chain assembly. Fmoc-D-4-Chlorophenylalanine allows researchers to introduce a D-configured amino acid bearing a para-chlorinated aromatic side chain into suitable peptide sequences. Its application depends on coupling efficiency, deprotection conditions, and compatibility with the resin and other building blocks used in the synthesis.
Pharmaceutical and Medicinal Chemistry Research
Halogenated amino acids are valuable building blocks in medicinal chemistry because chlorine substitution can influence molecular lipophilicity, electronic properties, and interactions with biological targets. Fmoc-D-4-Chlorophenylalanine may support the preparation of modified peptides and related research compounds for structure–activity relationship studies. Its D-configuration and para-chlorine substituent provide structural variables for investigating how stereochemistry and aromatic substitution affect molecular properties and biological behavior.
Organic Synthesis and Chemical Research
Modified Peptide and Structure–Activity Studies
D-amino acids are useful tools for studying the relationship between peptide stereochemistry, conformation, and molecular interactions. Fmoc-D-4-Chlorophenylalanine enables the introduction of a D-configured residue with a para-chlorinated phenyl group into suitable peptide designs. Comparing resulting peptides with L-configured or non-halogenated analogues can help researchers investigate how stereochemistry and side-chain substitution affect peptide properties, subject to experimental validation.
