Boc-N-Me-p-nitro-Phe-OH · DCHA

Boc-N-Me-p-nitro-Phe-OH · DCHA is a protected, N-methylated aromatic amino acid derivative bearing a para-nitro substituent on the phenyl ring, supplied as a dicyclohexylamine salt (DCHA). The Boc group on the amino nitrogen and the N-methyl substitution make it a useful building block for controlled amide formation and reduced backbone hydrogen-bonding during peptide assembly. The electron-withdrawing p-nitro side-chain supports downstream derivatization and provides a distinct handle for analytical tracking in synthetic workflows.

1. Peptide Building Block

Boc-N-Me-p-nitro-Phe-OH · DCHA is used as a specialty residue in peptide synthesis where N-methylation is required to modulate backbone conformation and amide hydrogen-bonding patterns. Researchers preparing constrained or protease-resistant peptide motifs commonly incorporate this residue into solution-phase or solid-phase workflows to introduce an aromatic side chain with a para-nitro functionality that can be carried through assembly and used for later functional conversion. The Boc protection and N-methyl substitution help ensure the residue behaves as a defined peptide-coupling unit rather than an unprotected amino acid, supporting reliable incorporation in custom peptide manufacturing and academic peptide chemistry.

2. Peptidomimetic And SAR Studies

Boc-N-Me-p-nitro-Phe-OH · DCHA serves as a practical intermediate for peptidomimetic development and structure-activity relationship (SAR) campaigns that require N-methylated aromatic positions. Medicinal chemistry groups often use this kind of residue to generate libraries of analogs where backbone N-methylation is used to tune conformational preferences and reduce the number of donor/acceptor sites available for intramolecular and intermolecular interactions. The para-nitro group provides a chemically distinctive substituent that can be retained for comparative studies or converted in later steps to access related aromatic functionalities, enabling efficient analog progression in lead optimization.

3. Pharmaceutical Intermediate Synthesis

Boc-N-Me-p-nitro-Phe-OH · DCHA is also used as a defined chiral aromatic amino acid building block for downstream pharmaceutical intermediate development. Process and R&D chemists value the protected amine and N-methyl substitution as a way to install a specific substitution pattern early in a synthetic sequence, while the para-nitro functionality offers a convenient site for later transformation into alternative substituted phenyl derivatives. This product format is particularly useful when a robust, isolable intermediate is needed to support multi-step synthesis planning for custom synthesis, scale-up development, and route scouting toward amide-containing targets.

4. Analytical Derivatization Handle

Boc-N-Me-p-nitro-Phe-OH · DCHA is employed in analytical and method-development contexts where a para-nitro aromatic group provides a strong, chemically addressable tag for monitoring derivatization steps and intermediate identity. Organic and peptide chemistry teams sometimes incorporate this residue into model compounds or peptide fragments to create standards that reflect the exact substitution pattern of interest, including N-methylation and Boc-protected amino functionality during early synthetic stages. The distinct electronic character of the p-nitro substituent supports clear differentiation of related aromatic intermediates during purification and characterization workflows, aiding quality control in research-grade synthesis.

1. Therapeutic potential of an intestinotrophic hormone, glucagon-like peptide 2, for treatment of type 2 short bowel syndrome rats with intestinal bacterial and fungal dysbiosis

2. Constitutive and inflammation-dependent antimicrobial peptides produced by epithelium are differentially processed and inactivated by the commensal Finegoldia magna and the pathogen Streptococcus pyogenes

3. A possible role of tachykinin-related peptide on an immune system activity of mealworm beetle, Tenebrio molitor L

4. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function

5. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis