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Reliable Supplier Boc-L-3-Chlorophenylalanine丨CAS 114873-03-9
Boc-L-3-Chlorophenylalanine is a protected amino acid derivative featuring a tert-butoxycarbonyl (Boc) protecting group on the amino functionality and a chlorine substituent at the 3-position of the phenyl ring. Its L-configuration, protected amino group, and halogenated aromatic side chain make it a useful building block for peptide synthesis, medicinal chemistry, and specialized organic synthesis. The Boc group enables controlled amino-group protection during multistep reactions, while the chlorinated phenyl side chain provides a structural feature for exploring modified peptides and functional molecules.
Chemical Identifiers
| InChI | InChI=1S/C14H18ClNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-5-4-6-10(15)7-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 |
| InChI Key | RCZHBTHQISEPPP-NSHDSACASA-N |
| Smiles | CC(C)(C)OC(=O)N[C@@H](CC1=CC(=CC=C1)Cl)C(=O)O |
| EC No. | |
| MDL No. | MFCD00672515 |
| PubChem CID | 2761465 |
Applications
Peptide Synthesis and Modified Peptide Development
Boc-protected amino acids are widely used in peptide synthesis and multistep organic chemistry to control the reactivity of amino groups. Boc-L-3-Chlorophenylalanine can introduce an L-configured, meta-chlorinated phenylalanine residue into suitable peptide sequences after appropriate deprotection and coupling. Its use depends on the selected synthesis strategy, reaction conditions, and compatibility with other protecting groups and reagents.
Pharmaceutical and Medicinal Chemistry Research
Halogenated amino acid derivatives are useful building blocks in medicinal chemistry because chlorine substitution can influence molecular lipophilicity, electronic properties, and interactions with biological targets. Boc-L-3-Chlorophenylalanine may support the preparation of modified peptides and amino-acid-derived compounds for structure–activity relationship studies. Researchers can compare chlorinated and non-chlorinated analogues to investigate how aromatic substitution affects molecular properties and biological behavior.
Organic Synthesis and Chemical Research
Biochemical and Structure–Activity Studies
Introducing non-standard amino acids into peptides allows researchers to investigate how side-chain modifications influence conformation, stability, and molecular recognition. Boc-L-3-Chlorophenylalanine can serve as a precursor for peptides containing a meta-chlorinated aromatic residue in the L-configuration. Comparisons with phenylalanine and other substituted amino acid analogues can help researchers evaluate the contribution of halogen substitution to peptide properties, subject to experimental validation.
