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Multiple Grade D-4-Chlorophenylalanine丨CAS 14091-08-8
D-4-Chlorophenylalanine is a halogenated derivative of D-phenylalanine, featuring a chlorine substituent at the para position of the aromatic ring. Its defined D-configuration and substituted phenyl group make it a valuable building block for peptide synthesis, medicinal chemistry, and specialized organic synthesis. The combination of stereochemical specificity and aromatic halogenation allows researchers to explore modified amino acid structures and investigate how these features influence molecular properties and biological interactions.
Chemical Identifiers
| InChI | InChI=1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1 |
| InChI Key | NIGWMJHCCYYCSF-MRVPVSSYSA-N |
| Smiles | C1=CC(=CC=C1C[C@H](C(=O)O)N)Cl |
| EC No. | 634-290-0 |
| MDL No. | MFCD00079675 |
| PubChem CID | 667429 |
Applications
Pharmaceutical Research and Drug Discovery
Halogenated amino acids are frequently investigated in medicinal chemistry because aromatic substitution can influence molecular conformation, lipophilicity, and interactions with biological targets. D-4-Chlorophenylalanine may serve as a building block for synthesizing peptide analogues and other compounds designed to investigate structure–activity relationships. Its D-configuration offers an additional structural variable for studying the effects of stereochemistry on molecular behavior.
Peptide Synthesis and Modified Peptide Development
D-amino acids are useful in peptide research when investigators seek to modify backbone conformation or explore resistance to enzymatic degradation. D-4-Chlorophenylalanine can be incorporated into suitable peptide sequences to introduce a D-configured aromatic residue with a para-chloro substituent. Its use depends on the selected coupling chemistry, protection strategy, and compatibility with the target peptide sequence.
Organic Synthesis and Chemical Research
Structure–Activity and Stereochemical Studies
The D-configuration and para-chlorinated aromatic ring make D-4-Chlorophenylalanine relevant to comparative molecular design. Researchers may use it alongside related L-amino acids or non-halogenated analogues to investigate the influence of stereochemistry and aromatic substitution on molecular recognition, peptide conformation, and biological activity. Conclusions about specific biological effects require experimental validation.
