Boc-N-Me-p-chloro-D-Phe-OH is a Boc-protected, N-methylated derivative of D-phenylalanine bearing a para-chloro substituent on the aromatic ring, placing it within the class of protected amino acid building blocks for peptide chemistry. The molecule contains a Boc carbamate protecting group on the amino terminus, an N-methyl substituent that modifies the backbone nitrogen, a free carboxylic acid group for coupling, and a chlorinated phenyl side chain that provides a distinct electron-withdrawing aromatic functionality while retaining the D stereochemical designation stated in the name. In synthesis, it functions as a stepwise amino acid residue suitable for controlled amide bond formation and incorporation into peptide-like structures where the para-chloro aryl group and N-methyl substitution are used to tune chemical properties, labeling handles, or structure-activity study analogs.
CAT No: CP26265
CAS No:125324-00-7
Synonyms/Alias:125324-00-7;Boc-Nalpha-methyl-4-chloro-D-phenylalanine;SCHEMBL5803685;BOC-D-MEPHE(4-CL)-OH;D-Phenylalanine,4-chloro-N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-;CTK4B4331;GVKQCRRZMAVASQ-GFCCVEGCSA-N;ZINC2560685;3152AD;AKOS015836749;SC-96090;TR-062365;K-1836;(2R)-2-(tert-Butoxycarbonyl-methylamino)-3-(4-chlorophenyl)propionicacid;(R)-2-(tert-butoxycarbonyl(methyl)amino)-3-(4-chlorophenyl)propanoicacid;Boc-4-chloro-D-MePhe-OH,(R)-2-(Boc-methyl-amino)-3-(4-chloro-phenyl)-propionicacid
Boc-N-Me-p-chloro-D-Phe-OH is a Boc-protected, N-methylated D-phenylalanine derivative bearing a para-chloro substituent on the aromatic ring. This non-natural, stereodefined amino acid building block is designed for peptide and peptidomimetic synthesis where steric and electronic effects from N-methylation and aryl chlorination are used to tune conformation and physicochemical properties. The Boc group supports standard protected-amino-acid coupling workflows, while the N-methyl functionality helps modulate backbone hydrogen-bonding patterns in the resulting peptide segments.
1. Peptidomimetic Segment Building
Boc-N-Me-p-chloro-D-Phe-OH is used as a defined amino acid segment in custom peptide and peptidomimetic synthesis, particularly when researchers need a D-configured residue with an N-methylated amide to influence local backbone conformation. Peptide chemistry groups incorporate this building block during solution-phase or solid-phase assembly to generate analogs with altered hydrogen-bonding capacity and modified steric profiles relative to unmodified phenylalanine. The para-chloro aromatic substitution further provides a handle for tuning hydrophobicity and aromatic electronics, supporting SAR-driven library construction where consistent stereochemistry and substitution pattern are required.
2. Solid-Phase Peptide Synthesis
Boc-N-Me-p-chloro-D-Phe-OH serves as a protected amino acid building block for solid-phase peptide synthesis workflows that require incorporation of an N-methylated D-amino acid. Peptide manufacturers and research labs use this reagent to assemble longer sequences where the N-methyl group is maintained through coupling and deprotection steps to preserve the intended amide substitution pattern in the final product. The Boc-protected amino terminus enables routine integration into protected-residue strategies, while the para-chloro side-chain substitution supports the preparation of chlorinated peptide analogs used in chemical biology and medicinal chemistry development programs.
3. Medicinal Chemistry SAR Libraries
Boc-N-Me-p-chloro-D-Phe-OH is commonly selected for medicinal chemistry efforts that build structure-activity relationship (SAR) libraries containing D-amino acid motifs and N-methylated backbone elements. In these workflows, the reagent provides a reproducible way to introduce a chlorinated phenyl side chain alongside an N-methylated amide, enabling systematic comparison of analogs that differ in backbone hydrogen-bonding and aromatic substitution. Chemical development teams value the defined stereochemistry and substitution pattern because downstream biological evaluation often depends on tight control over residue identity at specific positions within a lead peptide or peptidomimetic scaffold.
4. Conformational Control Studies
Boc-N-Me-p-chloro-D-Phe-OH supports chemical biology and biophysical research focused on conformational effects of N-methylation and D-amino acid incorporation. Researchers use this building block to generate peptide variants where backbone amide hydrogen-bonding is reduced by the N-methyl group and where the D-configuration can alter turn propensity and overall stereochemical presentation. The para-chloro aromatic substituent adds additional electronic and steric character, making this residue useful for designing analogs intended for structure-property studies such as secondary-structure propensity comparisons, receptor-binding motif mapping, or stability-oriented sequence optimization within a defined experimental series.
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