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Best Price Fmoc-L-4-Chlorophenylalanine丨CAS 175453-08-4
Fmoc-L-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 L-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 enables controlled amino-group protection during peptide assembly, while the modified aromatic side chain provides structural diversity for developing peptides and other 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-/m0/s1 |
| InChI Key | CQPNKLNINBUUOM-QFIPXVFZSA-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. | 695-934-4 |
| MDL No. | MFCD00080281 |
| PubChem CID | 2734471 |
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-L-4-Chlorophenylalanine enables the introduction of an L-configured amino acid bearing a para-chlorinated aromatic side chain into suitable peptide sequences. Its performance 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 useful building blocks in medicinal chemistry because chlorine substitution can influence molecular lipophilicity, electronic properties, and interactions with biological targets. Fmoc-L-4-Chlorophenylalanine may support the preparation of modified peptides and related research compounds for structure–activity relationship studies. Researchers can compare chlorinated and non-chlorinated analogues to investigate how para-substitution affects molecular properties and biological behavior.
Organic Synthesis and Chemical Research
Modified Peptide and Structure–Activity Studies
Non-standard amino acids allow researchers to investigate how side-chain modifications influence peptide conformation, stability, and molecular recognition. Fmoc-L-4-Chlorophenylalanine can be incorporated into suitable peptide designs to introduce a para-chlorinated aromatic residue while retaining the L-configuration. Comparisons with phenylalanine and other chlorophenylalanine isomers can help researchers examine how chlorine position affects peptide properties and molecular interactions, subject to experimental validation.
