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Top Supplier Boc-L-2-Chlorophenylalanine丨CAS 114873-02-8
Boc-L-2-Chlorophenylalanine is a protected non-standard amino acid featuring a tert-butoxycarbonyl (Boc) protecting group on the amino functionality and a chlorine substituent at the 2-position of the aromatic ring. Its L-configuration, Boc protection, and ortho-chlorinated phenyl side chain make it a useful building block for peptide synthesis, medicinal chemistry, and advanced organic synthesis. The Boc group supports controlled amino-group protection during multistep reactions, while the ortho-chlorine substituent 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)8-9-6-4-5-7-10(9)15/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 |
| InChI Key | TUUQJNHCVFJMPU-NSHDSACASA-N |
| Smiles | CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1Cl)C(=O)O |
| EC No. | 811-643-9 |
| MDL No. | MFCD00672514 |
| PubChem CID | 2761463 |
Applications
Peptide Synthesis and Modified Peptide Development
Boc-protected amino acids are widely used in peptide synthesis and multistep organic chemistry to manage amino-group reactivity. Boc-L-2-Chlorophenylalanine can introduce an L-configured amino acid bearing an ortho-chlorinated aromatic side chain into suitable peptide sequences following appropriate deprotection and coupling steps. Its use depends on the synthesis strategy, reaction conditions, and compatibility with other protecting groups and reagents.
Pharmaceutical and Medicinal Chemistry Research
Halogenated amino acids are valuable building blocks in medicinal chemistry because chlorine substitution can influence molecular lipophilicity, electronic distribution, and molecular interactions. Boc-L-2-Chlorophenylalanine may support the preparation of modified peptides and related compounds for structure–activity relationship studies. The position of the chlorine atom can also affect side-chain geometry and local steric properties, offering researchers another variable to investigate when designing and comparing molecular structures.
Organic Synthesis and Chemical Research
Modified Peptide and Structure–Activity Studies
Non-standard amino acids allow researchers to explore how side-chain modifications influence peptide conformation, stability, and molecular recognition. Boc-L-2-Chlorophenylalanine can serve as a precursor for peptides containing an L-configured, ortho-chlorinated aromatic residue. Comparisons with phenylalanine and other chlorinated phenylalanine isomers can help researchers investigate the effects of chlorine position on peptide properties, subject to experimental validation.
