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Best Quality Fmoc-L-3-Chlorophenylalanine丨CAS 198560-44-0
Fmoc-L-3-Chlorophenylalanine is a protected non-standard amino acid featuring a fluorenylmethoxycarbonyl (Fmoc) protecting group on the amino functionality and a chlorine substituent at the 3-position of the aromatic ring. Its L-configuration, Fmoc protection, and chlorinated phenyl side chain make it a valuable building block for solid-phase peptide synthesis, medicinal chemistry, and specialized organic synthesis. The Fmoc group enables controlled amino-group protection, while the modified aromatic side chain provides structural diversity for designing peptides and functional molecules.
Chemical Identifiers
| InChI | InChI=1S/C24H20ClNO4/c25-16-7-5-6-15(12-16)13-22(23(27)28)26-24(29)30-14-21-19-10-3-1-8-17(19)18-9-2-4-11-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/t22-/m0/s1 |
| InChI Key | UOZAKKJRIKXQPY-QFIPXVFZSA-N |
| Smiles | C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC(=CC=C4)Cl)C(=O)O |
| EC No. | |
| MDL No. | MFCD00672548 |
| PubChem CID | 2761466 |
Applications
Peptide Synthesis and Modified Peptide Development
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-3-Chlorophenylalanine enables the introduction of an L-configured phenylalanine residue with a chlorine substituent at the meta position into suitable peptide sequences. Its performance depends on coupling efficiency, deprotection conditions, and compatibility with the resin and other building blocks in the synthesis.
Pharmaceutical and Medicinal Chemistry Research
Halogenated amino acids are useful tools in medicinal chemistry because chlorine substitution can influence molecular lipophilicity, electronic properties, and interactions with biological targets. Fmoc-L-3-Chlorophenylalanine may serve as a precursor for modified peptides and amino-acid-derived compounds used in structure–activity relationship studies. Researchers can compare chlorinated and non-chlorinated analogues to investigate how aromatic substitution affects molecular properties and biological activity.
Organic Synthesis and Chemical Research
Modified Peptide and Structure–Activity Studies
Non-standard amino acids allow researchers to investigate how changes in side-chain structure influence peptide conformation, stability, and molecular recognition. Fmoc-L-3-Chlorophenylalanine can be incorporated into suitable peptide designs to introduce a meta-chlorinated aromatic residue while retaining the L-configuration. Comparisons with L-phenylalanine and other substituted amino acid analogues can help researchers evaluate the contribution of chlorine substitution to peptide properties, subject to experimental validation.
