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Top Fmoc-D-3-Chlorophenylalanine丨CAS 205526-23-4
Fmoc-D-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 D-configuration, Fmoc protection, and chlorinated phenyl side chain make it a specialized 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/c25-16-7-5-6-15(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-/m1/s1 |
| InChI Key | UOZAKKJRIKXQPY-JOCHJYFZSA-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. | 882-588-6 |
| MDL No. | MFCD00672549 |
| PubChem CID | 7020852 |
Applications
Peptide Synthesis and Modified Peptide Development
Fmoc-protected amino acids are widely used in solid-phase peptide synthesis (SPPS), where the Fmoc group is selectively removed under suitable basic conditions during peptide-chain assembly. Fmoc-D-3-Chlorophenylalanine can introduce a D-configured amino acid bearing a meta-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 useful building blocks in medicinal chemistry because chlorine substitution can influence molecular lipophilicity, electronic properties, and interactions with biological targets. Fmoc-D-3-Chlorophenylalanine may support the preparation of modified peptides and related research compounds for structure–activity relationship studies. Its D-configuration and chlorinated side chain 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 valuable tools for investigating the relationship between peptide stereochemistry, conformation, and molecular interactions. Fmoc-D-3-Chlorophenylalanine allows researchers to introduce a D-configured residue with a meta-chlorinated phenyl group into suitable peptide designs. Comparing these peptides with L-configured or non-halogenated analogues can help researchers assess the influence of stereochemistry and side-chain substitution on peptide properties, subject to experimental validation.
