Bz-DL-Phe-OH

Bz-DL-Phe-OH is a benzyl-protected phenylalanine acid derivative in which the amino group is acylated as a benzyloxycarbonyl (Cbz/Bz) carbamate while the carboxylic acid remains free, giving a chiral amino acid framework with a stereocenter at the α-carbon. The molecule combines a rigid phenyl side chain with an aromatic carbamate protecting group, enabling predictable peptide-coupling behavior while maintaining orthogonal reactivity between the protected nitrogen and the free carboxyl functionality. The DL designation indicates a racemic mixture at the stereogenic center, which is relevant for method development, material synthesis, and intermediate preparation where racemate handling is acceptable. As a protected amino acid derivative, Bz-DL-Phe-OH can participate in standard peptide-bond formation after activation of the carboxylic acid and can undergo protecting-group manipulations to support downstream synthesis of phenylalanine-containing sequences and analogs.

1. Peptide Synthesis

Bz-DL-Phe-OH serves as a Cbz-protected amino acid building block for peptide coupling chemistry in solid-phase or solution-phase synthesis workflows. The free carboxylic acid enables activation for amide bond formation, while the carbamate-protected amine suppresses undesired side reactions during coupling and subsequent chain elongation. Racemic stereochemistry at the α-carbon supports preparation of phenylalanine-containing peptides or peptide fragments where stereochemical uniformity is not required, such as method screening, library synthesis, or comparative SAR scaffolds. Downstream deprotection of the carbamate can restore the phenylalanine amino functionality for iterative peptide assembly and for generating peptide intermediates compatible with further functionalization.

2. Chiral Synthesis Studies

Bz-DL-Phe-OH is suitable for stereochemical research and chiral process development because it provides a racemic, N-protected phenylalanine acid platform with a defined protecting group identity. The α-stereocenter bearing the phenyl side chain can be used to evaluate stereoselective coupling conditions, racemization sensitivity, and protecting-group stability under activation and deprotection regimes. The Cbz/Bz carbamate offers a chemically robust handle for investigating how stereochemical outcomes propagate through peptide bond formation and subsequent transformations. The resulting derivatives can be used to compare stereochemical distributions in downstream peptide analogs, analytical standards, or intermediate streams in chiral manufacturing route design.

3. Side-Chain Functionalization

Bz-DL-Phe-OH supports synthetic organic chemistry routes that modify the phenylalanine side chain while retaining the protected amino group for controlled sequential chemistry. The phenyl side chain can be leveraged for electrophilic aromatic substitution, oxidative functionalization, or conversion into substituted aromatic motifs that are common in peptidomimetic and medicinal chemistry fragments. The free carboxylic acid allows retention of a handle for conversion into activated esters or amide-linked intermediates after side-chain derivatization, enabling two-stage synthesis strategies. Downstream utility includes preparation of substituted phenylalanine analogs, aromatic-tagged peptide building blocks, and intermediates for constructing structure-defined scaffolds used in biochemical research and applied chemical development.

4. Analytical Research Standards

Bz-DL-Phe-OH functions as a reference material for analytical method development targeting protected amino acids, carbamate stability, and peptide-coupling intermediates. The combination of a benzyl-derived carbamate and a free carboxylic acid produces characteristic chromatographic and spectroscopic signatures that can be used to track protection state, monitor deprotection completeness, and validate identity during synthesis of phenylalanine derivatives. Racemic composition can be specifically relevant for calibrating chiral chromatography workflows, assessing racemization during coupling, or establishing method baselines for DL amino acid handling. Downstream derivative formation includes use as a starting point for labeled or derivatized standards, supporting routine quality control of protected amino acid chemistry in research and specialty chemical manufacturing.

5. Pharmaceutical Intermediate Preparation

Bz-DL-Phe-OH can be employed as a process chemistry intermediate for manufacturing of phenylalanine-containing protected fragments used in peptide-like drug substance synthesis and related fine chemical production. The N-protected carbamate structure is compatible with common activation strategies for carboxylic acids, while the free acid allows conversion into coupling-ready forms without requiring immediate transformation of the amino protection. The racemic starting material can be practical for producing non-stereochemically constrained intermediates, for generating building blocks for further resolution steps, or for supporting parallel synthesis routes where stereochemistry is introduced later. Downstream utility includes preparation of C-terminal or side-chain-modified phenylalanine derivatives, enabling scalable intermediate generation for industrial peptide chemistry and specialty chemical production pipelines.

1. Tachykinin-related peptides modulate immune-gene expression in the mealworm beetle Tenebrio molitor L

2. Cationic cell-penetrating peptides are potent furin inhibitors

3. Investigating Potential Interactions Between Neurohypophyseal Peptides, their Drug Analogs, and Coagulation Factor VIII

4. The spatiotemporal control of signalling and trafficking of the GLP-1R

5. Characterization of Novel P-Selectin Targeted Complement Inhibitors in Murine Models of Hindlimb Injury and Transplantation