Bzl-D-Phe-OMe*HCl is a protected, stereochemically defined amino acid derivative of D-phenylalanine in which the carboxyl group is present as a methyl ester (Phe-OMe) and the amino functionality is benzylated (Bzl), yielding a benzyl-protected amino ester hydrochloride salt. The molecule contains a benzyl-protected α-amino group, a methyl ester carbonyl, and a free carboxylate-equivalent ester linkage, with the "*HCl" indicating association with hydrochloride to form a salt that can modify the handling and protonation state of the amino function. In peptide and amino acid synthesis workflows, benzyl-protected amino esters of this type are used as intermediates for stepwise assembly and for preparing more complex phenylalanine-containing derivatives, while the D-configuration supports stereochemical studies and incorporation of non-L stereochemistry into chemical biology constructs.
CAT No: CP26065
CAS No:84028-90-0
Synonyms/Alias:N-Benzyl-D-phenylalanine methyl ester*HCl
Chemical Name:N-Benzyl-D-phenylalanine methyl ester hydrochloride
Bzl-D-Phe-OMe*HCl is a D-configured phenylalanine methyl ester hydrochloride bearing a benzyl (Bzl) protecting group on the amino functionality, with the carboxyl group present as a methyl ester. The chiral center at the alpha-carbon and the aromatic side chain of the D-phenylalanine unit support stereochemically controlled peptide and peptidomimetic construction, while the benzyl-protected amine and ester carbonyl define orthogonal reactivity windows. The hydrochloride salt form improves handling of the protected amino ester by establishing a defined amine protonation state, which can influence coupling behavior and downstream deprotection planning. The combination of an N-protected amino ester and a stable aromatic side chain makes the compound a practical chiral amino acid intermediate for protected amino acid synthesis, peptide building block preparation, and selective functional group transformations.
1. Peptide Synthesis
Bzl-D-Phe-OMe*HCl is used in peptide synthesis workflows where an N-benzyl-protected D-phenylalanine methyl ester serves as a protected amino acid building block. The benzyl-protected amine supports peptide coupling after appropriate activation, while the methyl ester can be converted to a carboxylate or acid equivalent for C-terminal incorporation depending on the synthetic sequence. The D-stereochemistry enables access to D-amino acid-containing peptides that are compatible with stereodefined amide bond formation and subsequent deprotection strategies. The hydrochloride salt form can facilitate controlled handling of the protected amino ester during coupling and intermediate preparation, supporting downstream assembly of peptide analogs and research-grade oligomers.
2. Chiral Building Blocks
Bzl-D-Phe-OMe*HCl functions as a chiral amino acid intermediate for stereoselective synthesis of D-phenylalanine derivatives and related chiral fragments. The preserved alpha-chirality and the benzyl-protected nitrogen provide a defined stereochemical handle for constructing dipeptides, cyclic peptidomimetics, and stereochemically constrained scaffolds. The methyl ester form can be employed as a controlled carboxylate equivalent in synthetic planning, enabling downstream conversion to amide-forming acid derivatives or participation in ester-based derivatization steps. The aromatic side chain offers a stable platform for further functionalization or for maintaining hydrophobic recognition motifs in molecular design and chiral library generation.
3. Peptidomimetic Construction
Bzl-D-Phe-OMe*HCl is suitable for peptidomimetic construction where D-phenylalanine units are incorporated to modulate conformation, proteolytic stability, and binding-site geometry in non-natural peptide-like structures. The N-benzyl protection strategy supports stepwise assembly by allowing selective deprotection and re-protection logic during scaffold elaboration, while the ester functionality can be leveraged for controlled transformation into amide or other carbonyl-linked motifs. The aromatic side chain enables hydrophobic and pi-interaction contributions that are commonly exploited in structure-activity relationship studies and fragment-based molecular design. The compound's defined stereochemistry supports reproducible incorporation into larger analogs used for biochemical research intermediate preparation and systematic analog generation.
4. Chemical Manufacturing Intermediates
Bzl-D-Phe-OMe*HCl can be applied as a process chemistry intermediate in fine chemical synthesis routes that require a protected D-amino acid ester with an orthogonal N-protection element. The benzyl-protected amine and methyl ester establish a manufacturable protected form that can be routed through activation, coupling, and subsequent functional group interconversion to produce downstream amino acid derivatives. The hydrochloride salt form supports practical isolation and handling in industrial intermediate preparation, enabling consistent feedstock behavior in multi-step manufacturing sequences. The compound's structural features align with scalable amino acid derivative production where stereochemical integrity and protected functional group management are central to reliable downstream conversion.
5. Analytical Research Standards
Bzl-D-Phe-OMe*HCl is used in analytical research settings to support method development and reference material preparation for stereochemically defined amino acid derivatives. The combination of D-configuration, benzyl-protected amine, and methyl ester provides a distinct chemical signature that can be leveraged for chromatographic and spectrometric identification of protected amino acid intermediates. The hydrochloride salt form can aid reproducible sample preparation and can support comparative analysis during protection, coupling, and deprotection process monitoring. The compound thereby serves as a practical analytical anchor for verifying stereochemical outcomes and functional group transformations in amino acid chemistry and peptide synthesis development.
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