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Best Supplier Fmoc-L-3,4-Dichlorophenylalanine丨CAS 177966-59-5
Fmoc-L-3,4-Dichlorophenylalanine is a protected derivative of L-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 L-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. The combination of stereochemical specificity and aromatic substitution supports the preparation of structurally defined peptides and modified amino acid derivatives.
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-/m0/s1 |
| InChI Key | QNVHCYWPXIGFGN-QFIPXVFZSA-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. | 810-601-7 |
| MDL No. | MFCD00273473 |
| PubChem CID | 7020437 |
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-L-3,4-Dichlorophenylalanine can introduce an L-configured amino acid bearing a dichlorinated aromatic side chain into suitable peptide sequences. Its use depends on the coupling conditions, deprotection strategy, and compatibility with the resin and other building blocks in the synthesis.
Peptide Synthesis and Modified Peptide Development
Boc-protected amino acids are widely used in peptide synthesis to control amino-group reactivity during multistep assembly. Boc-D-3,4-Dichlorophenylalanine can be used to introduce a D-configured amino acid with a dichlorinated aromatic side chain into suitable peptide sequences. Its application depends on the selected coupling chemistry, deprotection strategy, and compatibility with other building blocks in the target sequence.
Organic Synthesis and Chemical Research
Structure–Activity and Stereochemical Studies
Incorporating non-standard amino acids into peptide sequences allows researchers to investigate how aromatic substitution affects conformation, stability, and molecular recognition. Fmoc-L-3,4-Dichlorophenylalanine may be used to develop peptide analogues containing a 3,4-dichlorinated phenyl side chain. Comparative studies with non-halogenated or differently substituted analogues can help clarify the contribution of aromatic substitution to molecular properties, subject to experimental validation.
