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Bulk Supply Fmoc-D-3,4-Dichlorophenylalanine丨CAS 177966-58-4
Fmoc-D-3,4-Dichlorophenylalanine is a protected derivative of D-3,4-dichlorophenylalanine, featuring a fluorenylmethoxycarbonyl (Fmoc) protecting group on the amino functionality and chlorine substituents at the 3- and 4-positions of the aromatic ring. Its defined D-configuration, Fmoc protection, and dichlorinated phenyl side chain make it a specialized building block for solid-phase peptide synthesis, medicinal chemistry, and advanced organic synthesis. These structural features enable researchers to explore modified peptide sequences and investigate how stereochemistry and aromatic substitution influence molecular properties.
Chemical Identifiers
| InChI | InChI=1S/C24H19Cl2NO4/c25-20-10-9-14(11-21(20)26)12-22(23(28)29)27-24(30)31-13-19-17-7-3-1-5-15(17)16-6-2-4-8-18(16)19/h1-11,19,22H,12-13H2,(H,27,30)(H,28,29)/t22-/m1/s1 |
| InChI Key | QNVHCYWPXIGFGN-JOCHJYFZSA-N |
| Smiles | C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@H](CC4=CC(=C(C=C4)Cl)Cl)C(=O)O |
| EC No. | |
| MDL No. | MFCD00273473 |
| PubChem CID | 2756115 |
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 during peptide-chain assembly. Fmoc-D-3,4-Dichlorophenylalanine can introduce a D-configured amino acid bearing a dichlorinated aromatic side chain into suitable peptide sequences. Its application depends on the coupling method, 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 substituents can influence molecular lipophilicity, electronic properties, and interactions with biological targets. Fmoc-D-3,4-Dichlorophenylalanine may serve as an intermediate for preparing modified peptides and related research compounds used to investigate structure–activity relationships. Its D-configuration provides an additional structural feature for studying the effects of stereochemistry on molecular conformation and biological behavior.
Organic Synthesis and Chemical Research
Structure–Activity and Stereochemical Studies
Non-standard amino acids allow researchers to investigate how changes in stereochemistry and side-chain structure affect peptide conformation, stability, and molecular recognition. Fmoc-D-3,4-Dichlorophenylalanine may be used to develop peptide analogues containing a D-configured, dichlorinated aromatic residue. Comparisons with L-configured, non-halogenated, or differently substituted analogues can help researchers evaluate the influence of these structural features, subject to experimental validation.
