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Boc-D-2,4-Dichlorophenylalanine丨CAS 114873-12-0 Manufacturer
Boc-D-2,4-Dichlorophenylalanine is a protected non-natural amino acid used in peptide synthesis, medicinal chemistry, and specialty organic synthesis. It features a D-configured phenylalanine backbone with chlorine substituents at the 2- and 4-positions of the aromatic ring and a tert-butoxycarbonyl (Boc) protecting group on the amino functionality. This combination provides a useful building block for introducing defined stereochemistry and a dichlorinated aromatic side chain into synthetic peptides and other target molecules.
Chemical Identifiers
| InChI | InChI=1S/C14H17Cl2NO4/c1-14(2,3)21-13(20)17-11(12(18)19)6-8-4-5-9(15)7-10(8)16/h4-5,7,11H,6H2,1-3H3,(H,17,20)(H,18,19)/t11-/m1/s1 |
| InChI Key | KSDWBXFRQWMWHO-LLVKDONJSA-N |
| Smiles | CC(C)(C)OC(=O)N[C@H](CC1=C(C=C(C=C1)Cl)Cl)C(=O)O |
| EC No. | 885-472-3 |
| MDL No. | MFCD01862941 |
| PubChem CID | 7010031 |
Applications
Applications in Peptide Synthesis
Boc-D-2,4-Dichlorophenylalanine can be used to prepare modified peptides and peptide analogues containing D-amino acid residues. The Boc group temporarily protects the amino functionality during synthesis and can be removed under suitable acidic conditions to enable subsequent coupling steps. Incorporating the D-configuration and dichlorinated aromatic side chain allows researchers to investigate how stereochemistry and side-chain substitution influence peptide conformation, stability, and biological properties.
Pharmaceutical and Medicinal Chemistry Research
In medicinal chemistry, Boc-D-2,4-Dichlorophenylalanine serves as a potential synthetic intermediate for peptide-based candidates and other molecules containing non-natural amino acid units. Its dichlorinated phenyl group provides a defined structural feature for exploring structure–activity relationships, while the D-configuration offers an alternative to naturally occurring L-amino acid residues. The Boc protecting group supports controlled functional-group management in multistep synthesis.
Applications in Organic Synthesis
Applications in Non-Natural Amino Acid Research
This compound is relevant to research involving D-amino acids and modified peptide building blocks. Its defined stereochemistry and protected amino group help facilitate the planned assembly of specialized sequences and synthetic libraries. Researchers may use it to investigate how D-amino acid incorporation affects peptide architecture, molecular recognition, and resistance to enzymatic degradation, depending on the target sequence and experimental design.
