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Perfect Supplier Boc-D-3-Chlorophenylalanine丨CAS 80102-25-6
Boc-D-3-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 3-position of the aromatic ring. Its D-configuration and chlorinated phenyl side chain make it a specialized 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 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-/m1/s1 |
| InChI Key | RCZHBTHQISEPPP-LLVKDONJSA-N |
| Smiles | CC(C)(C)OC(=O)N[C@H](CC1=CC(=CC=C1)Cl)C(=O)O |
| EC No. | |
| MDL No. | MFCD00672516 |
| PubChem CID | 7020827 |
Applications
Peptide Synthesis and Modified Peptide Development
Boc-protected amino acids are commonly used in peptide synthesis and organic chemistry to manage amino-group reactivity. Boc-D-3-Chlorophenylalanine can be used to introduce a D-configured, meta-chlorinated phenylalanine residue into suitable peptide sequences following appropriate deprotection and coupling steps. Its application depends on the synthesis route, reaction conditions, and compatibility with other protecting groups and reagents.
Pharmaceutical and Medicinal Chemistry Research
Halogenated amino acid derivatives are valuable building blocks for investigating how structural modifications affect molecular properties. Boc-D-3-Chlorophenylalanine may support the preparation of modified peptides and related research compounds for structure–activity relationship studies. Its D-configuration and chlorine substituent offer two distinct structural variables for exploring the effects of stereochemistry and aromatic substitution on molecular recognition and biological behavior.
Organic Synthesis and Chemical Research
Biochemical and Structure–Activity Studies
The incorporation of D-amino acids can influence peptide conformation and interactions with biological systems. Boc-D-3-Chlorophenylalanine allows researchers to introduce a D-configured residue bearing a meta-chlorinated aromatic side chain into suitable peptide designs. Comparing resulting compounds with L-configured or non-halogenated analogues can help investigate how stereochemistry and side-chain substitution affect peptide properties, subject to experimental validation.
