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High Purity Fmoc-D-2-Chlorophenylalanine丨CAS 205526-22-3
Fmoc-D-2-Chlorophenylalanine is a protected non-standard amino acid featuring a fluorenylmethoxycarbonyl (Fmoc) protecting group on the amino functionality and a chlorine substituent at the 2-position of the aromatic ring. Its D-configuration, Fmoc protection, and ortho-chlorinated phenyl side chain make it a specialized 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 provides structural diversity for designing peptides and other functional molecules.
Chemical Identifiers
| InChI | InChI=1S/C24H20ClNO4/c25-21-12-6-1-7-15(21)13-22(23(27)28)26-24(29)30-14-20-18-10-4-2-8-16(18)17-9-3-5-11-19(17)20/h1-12,20,22H,13-14H2,(H,26,29)(H,27,28)/t22-/m1/s1 |
| InChI Key | RNNKPNPLIMFSDY-JOCHJYFZSA-N |
| Smiles | C1=CC=C(C(=C1)C[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)Cl |
| EC No. | |
| MDL No. | MFCD00672547 |
| PubChem CID | 7020849 |
Applications
Solid-Phase Peptide Synthesis
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-2-Chlorophenylalanine can introduce a D-configured amino acid with an ortho-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-2-Chlorophenylalanine may support the preparation of modified peptides and related research compounds for structure–activity relationship studies. Its D-configuration and ortho-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 investigating how stereochemistry influences peptide conformation and molecular interactions. Fmoc-D-2-Chlorophenylalanine allows researchers to introduce a D-configured residue bearing an ortho-chlorinated aromatic side chain into suitable peptide designs. Comparisons with L-configured or non-halogenated analogues can help researchers assess how stereochemistry and chlorine substitution affect peptide properties, subject to experimental validation.
