N-α-Benzyl-D-Phenylalanine methyl ester hydrochloride is a D-phenylalanine-derived amino acid methyl ester bearing an N-α benzyl protecting group, where the phenylalanine side chain provides a hydrophobic benzyl substituent on the α-carbon. The molecule contains a methyl ester at the carboxyl terminus and a secondary amide-like nitrogen protected as an N-benzyl substituent, with the hydrochloride salt form indicating protonation of the amine functionality and improving handling of the ester. In peptide and amino-acid derivative synthesis, this protected ester is used as a substrate building block for controlled coupling chemistry and for preparing further phenylalanine-containing intermediates, while the D-configuration supports stereochemically defined structure-activity and labeling studies.
CAT No: CP01614
N-α-Benzyl-D-Phenylalanine methyl ester hydrochloride is a D-configuration phenylalanine methyl ester bearing an α-N-benzyl protecting group and a hydrochloride counterion that forms a salt at the amino functionality. The molecule contains a chiral α-carbon, a benzylated amide-forming nitrogen equivalent, and a methyl ester that can participate in esterification-amidation sequences or be converted into other acyl derivatives. Aromatic side-chain and benzyl substituents provide hydrophobic character and conformational bias, while the ester group enables controlled transformations during protected amino acid synthesis and peptide coupling planning. The salt form improves handling of the amino ester intermediate and supports downstream derivatization where the amino terminus is required to be protected and stereochemistry must be preserved.
1. Protected Amino Acid Synthesis
N-α-Benzyl-D-Phenylalanine methyl ester hydrochloride serves as a chiral amino acid ester intermediate for protected amino acid synthesis and stereocontrolled acyl chemistry. The α-N-benzyl group functions as an amino-protecting strategy that can be maintained through ester activation steps and then removed or exchanged under appropriate conditions to reveal the free amine for coupling. The methyl ester can be activated to form acylating species compatible with peptide coupling chemistry, while the D-stereocenter supports preparation of D-amino acid containing sequences and chiral building blocks. Downstream processing can convert the ester into amides, generate carboxylic acid derivatives, or support iterative synthesis of protected fragments used in fine chemical and peptide manufacturing workflows.
2. Peptide Coupling Chemistry
N-α-Benzyl-D-Phenylalanine methyl ester hydrochloride is applied in peptide building block preparation where controlled N-protection and ester-to-acyl conversion are required. The combination of a benzyl-protected amino functionality and a methyl ester provides a defined electrophile/latent acid handle that can be transformed into coupling-ready intermediates for amide bond formation. The D-phenylalanine stereochemistry can be incorporated to generate peptide analogs with altered backbone recognition, protease stability profiles, or conformational preferences relevant to peptide science and peptidomimetic construction. The aromatic side chain enables hydrophobic interactions in synthetic targets, supporting the assembly of D-amino acid enriched fragments for research-grade peptide synthesis and SAR studies.
3. Peptidomimetics And SAR Studies
N-α-Benzyl-D-Phenylalanine methyl ester hydrochloride supports peptidomimetic and structure-activity relationship studies by enabling the introduction of a D-phenylalanine residue into constrained or modified scaffolds. The preserved chiral center and protected amino group allow systematic variation of neighboring functional groups while maintaining stereochemical integrity during scaffold elaboration. The ester functionality can be used to generate alternative functional handles such as carboxamide or acid derivatives that influence hydrogen-bonding patterns and overall polarity in analog libraries. Downstream synthesis can produce D-amino acid substituted fragments for molecular design campaigns aimed at mapping how stereochemistry and aromatic side-chain placement affect binding motifs and chemical recognition.
4. Chemical Biology Labeling
N-α-Benzyl-D-Phenylalanine methyl ester hydrochloride can be employed in chemical biology workflows that require defined aromatic amino acid building blocks for tagging or conjugation chemistry. The benzyl-protected amino group provides a stable nitrogen protection state during functional group installation, while the methyl ester can be transformed into reactive acyl derivatives suitable for subsequent conjugation steps. The aromatic rings present in the phenylalanine side chain and N-benzyl group can be leveraged for hydrophobic anchoring in labeled probes or for incorporation into affinity-oriented constructs used in biomolecule interaction studies. The hydrochloride salt form assists handling of the amino ester during synthesis of labeling reagents and downstream preparation of modified peptide or protein fragments.
5. Pharmaceutical Intermediate Preparation
N-α-Benzyl-D-Phenylalanine methyl ester hydrochloride is suitable for pharmaceutical intermediate preparation where chiral, protected amino acid derivatives are required for controlled synthesis of acylated intermediates. The α-N-benzyl protection strategy supports chemoselective transformations by keeping the amino functionality masked while the ester group is converted into acyl derivatives used in stepwise assembly of larger molecules. D-configuration enables access to stereochemically defined intermediates used in the construction of non-proteinogenic or stereochemically modified building blocks that may be incorporated into medicinal chemistry programs. The aromatic side chain and ester-derived functionality support downstream conversion into amide-linked fragments, enabling scalable fine chemical synthesis routes for complex chiral scaffolds.
6. Process Chemistry And Fine Chemical Synthesis
N-α-Benzyl-D-Phenylalanine methyl ester hydrochloride is applicable to process chemistry and fine chemical synthesis as a chiral amino acid ester platform for manufacturing intermediate generation. The hydrochloride salt and N-benzyl protection can improve operational stability during handling and allow sequential transformations that preserve the D-stereocenter. The methyl ester provides a practical handle for activation chemistry and subsequent conversion to amide or acid forms, supporting route design for producing protected D-amino acid derivatives at scale. The resulting intermediates can feed into peptide building block preparation, stereodefined fragment synthesis, and specialty chemical production where consistent stereochemistry and protected-group compatibility are central to reproducible manufacturing.
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