N-Me-Phe-OBzl · p-tosylate

N-Me-Phe-OBzl · p-tosylate is a phenylalanine-derived, N-methylated amino acid ester salt in which the carboxyl functionality is present as a benzyl ester (OBzl) and the amino terminus is N-methylated (N-Me), while the counterion is p-toluenesulfonate (p-tosylate). The molecule retains the stereogenic α-carbon characteristic of phenylalanine, enabling stereodefined incorporation into peptide-like frameworks, and it presents a benzyl-protected carboxyl group that can participate in peptide coupling after appropriate activation or deprotection. The p-tosylate counterion improves handling of the amine salt form and can influence solubility and crystallization behavior during protected amino acid synthesis and downstream transformations. The combination of an N-methylated amide-forming nitrogen equivalent and a benzyl ester provides a controlled reactivity profile suitable for stepwise derivatization, peptide building block preparation, and chiral intermediate workflows.

1. Protected Amino Acid Synthesis

N-Me-Phe-OBzl · p-tosylate supports protected amino acid synthesis workflows where a stereodefined phenylalanine scaffold must be carried through multiple functional group manipulations. The N-methylated amino functionality and benzyl ester (OBzl) define a protected amino acid derivative with reduced risk of undesired side reactions compared with free amines or acids. The p-tosylate counterion helps maintain the salt form during handling, enabling consistent conversion to activated coupling partners or controlled deprotection sequences for peptide building block preparation. Downstream processing can generate N-methyl phenylalanine derivatives that remain compatible with standard peptide coupling chemistries used in research-grade and process-oriented fine chemical synthesis.

2. Peptide Coupling Building Blocks

N-Me-Phe-OBzl · p-tosylate is suitable for peptide coupling chemistry and peptide analog construction where an N-methylated phenylalanine residue is required to modulate backbone conformation. The benzyl ester can be transformed into an activated carboxyl equivalent for amide bond formation, while the stereogenic center supports incorporation of a defined configuration into growing peptide chains. The N-methyl group functions as a peptide backbone modification handle, enabling synthesis of N-methylated peptides and peptidomimetic segments that can be used for conformational studies and scaffold diversification. The salt form and protected functional groups help maintain integrity during iterative coupling and deprotection steps typical of peptide building block preparation.

3. Peptidomimetics And SAR Studies

N-Me-Phe-OBzl · p-tosylate can be applied in peptidomimetic construction and structure-activity relationship studies where N-methylation and phenyl side-chain presentation are used as systematic design variables. The phenylalanine side chain provides an aromatic handle for hydrophobic and π-interaction contributions, while the N-methylated α-amino component introduces backbone constraint effects relevant to SAR mapping in peptide-like series. The protected ester and salt-form amino functionality enable stepwise assembly of analog libraries by supporting controlled conversion to coupling-ready intermediates and subsequent chain elongation. Resulting N-methyl phenylalanine-containing fragments can serve as defined substructures for generating analogs used in biochemical research intermediate development and molecular scaffold optimization.

4. Chemical Biology Labeling

N-Me-Phe-OBzl · p-tosylate supports chemical biology workflows that require incorporation of a phenylalanine-derived residue into labeled or functionalized peptide constructs. The aromatic side chain and stereodefined backbone facilitate placement of the residue within peptide tags, affinity probes, or detection reagents where controlled amide formation is necessary. The N-methylated backbone segment can be leveraged to tune stability against enzymatic proteolysis in peptide-based labeling constructs, while the benzyl ester protection strategy enables selective downstream transformations aligned with labeling schedules. The p-tosylate salt form can improve reproducibility of intermediate preparation for conjugation-ready derivatives used in applied biochemical research.

5. Process Chemistry Intermediate

N-Me-Phe-OBzl · p-tosylate is applicable as a chiral amino acid intermediate in process chemistry and specialty chemical production where protected phenylalanine derivatives must be manufactured with reliable handling characteristics. The presence of a benzyl ester and N-methylated amino functionality supports a protected-group strategy that can be integrated into multi-step routes, including activation for coupling and controlled deprotection to reveal carboxyl functionality when needed. The p-tosylate counterion can influence physical properties such as crystallinity and solubility, which are relevant to scale-up planning and in-process control of protected amino acid intermediates. Downstream conversion to N-methyl phenylalanine derivatives enables production of peptide building blocks and peptidomimetic fragments used across industrial fine chemical synthesis and biochemical research supply chains.

1. Glucagonlike peptide 2 analogue teduglutide: stimulation of proliferation but reduction of differentiation in human Caco-2 intestinal epithelial cells

2. Identification, Localization in the Central Nervous System and Novel Myostimulatory Effect of Allatostatins in Tenebrio molitor Beetle

3. Genetic, cellular, and structural characterization of the membrane potential-dependent cell-penetrating peptide translocation pore

4. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes

5. Low bone turnover and low BMD in Down syndrome: effect of intermittent PTH treatment