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Bulk Supply Boc-D-2-Chlorophenylalanine丨CAS 80102-23-4
Boc-D-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 D-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 modified aromatic side chain provides structural diversity for developing specialized 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-/m1/s1 |
| InChI Key | TUUQJNHCVFJMPU-LLVKDONJSA-N |
| Smiles | CC(C)(C)OC(=O)N[C@H](CC1=CC=CC=C1Cl)C(=O)O |
| EC No. | |
| MDL No. | MFCD00801056 |
| PubChem CID | 7021188 |
Applications
Peptide Synthesis and Modified Peptide Development
Boc-protected amino acids are commonly used in peptide synthesis and multistep organic chemistry to control amino-group reactivity. Boc-D-2-Chlorophenylalanine can introduce a D-configured amino acid with an ortho-chlorinated aromatic side chain 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 valuable tools in medicinal chemistry because chlorine substitution can influence molecular lipophilicity, electronic properties, and molecular interactions. Boc-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 exploring 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 the relationship between peptide stereochemistry, conformation, and molecular interactions. Boc-D-2-Chlorophenylalanine can serve as a precursor for peptides containing a D-configured, ortho-chlorinated aromatic residue. Comparisons with L-configured analogues, unmodified phenylalanine, or other chlorinated phenylalanine isomers can help researchers investigate how stereochemistry and chlorine position influence peptide properties, subject to experimental validation.
