Description

n-Boc-1-Phenylmethyl-D-Histidine is a protected derivative of the non-natural D-enantiomer of the amino acid histidine, featuring a tert-butoxycarbonyl (Boc) group on the imidazole nitrogen and a benzyl (phenylmethyl) group on the α-amino nitrogen. This specific configuration makes it a crucial chiral building block for the synthesis of complex peptides and peptidomimetics, particularly in pharmaceutical research and development. It is primarily utilized by medicinal chemists and process development scientists in the biotechnology and pharmaceutical industries for creating novel therapeutic candidates, including enzyme inhibitors and receptor modulators.

Application

• Pharmaceutical Intermediate: A key chiral synthon in the research-scale synthesis of peptide-based drugs and bioactive molecules.
• Peptidomimetic Development: Used to incorporate a protected D-histidine residue into peptidomimetic scaffolds to enhance metabolic stability and binding affinity.
• Protease Inhibitor Research: Serves as a building block for developing inhibitors targeting specific proteases, such as renin or HIV protease.
• Chemical Biology Probes: Employed in the synthesis of labeled or modified peptides for studying protein-protein interactions and enzyme mechanisms.
• Asymmetric Synthesis: Utilized as a starting material or intermediate in the asymmetric synthesis of more complex, non-proteinogenic amino acid derivatives.
• GPCR Ligand Development: Incorporated into the structure of potential ligands for G-protein-coupled receptors (GPCRs) where histidine plays a critical role.

Basic Information

Item	Details
Product Name	n-Boc-1-Phenylmethyl-D-Histidine
CAS No.	65717-64-8
Molecular Formula	C20H27N3O4
Molecular Weight	373.45 g/mol
Synonyms	N-α-Boc-N-π-benzyl-D-histidine; (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(1H-imidazol-4-yl)propanoic acid (related Fmoc variant); Boc-His(Bzl)-OH (D-form); tert-Butyl (R)-1-((benzyloxy)carbonyl)-2-(1H-imidazol-5-yl)ethylcarbamate; D-Histidine, N-[(1,1-dimethylethoxy)carbonyl]-N-(phenylmethyl)-; N-Boc-N'-benzyl-D-histidine; Boc-D-His(Bzl)-OH; (R)-2-(tert-Butoxycarbonyl(benzyl)amino)-3-(1H-imidazol-4-yl)propanoic acid
EINECS	Contact for details

Quality Control

Our n-Boc-1-Phenylmethyl-D-Histidine is manufactured under a strict quality management system. Each batch undergoes comprehensive analytical testing, including HPLC for purity and chiral purity assessment, to ensure it meets the high standards required for research and development applications. Certificates of Analysis (COA) with detailed chromatographic data are provided and available upon request to support your regulatory and quality documentation needs.

Storage

Preserve in a tightly closed container, protected from light. Store in a cool, dry place at a controlled room temperature (15-25°C). This compound is hygroscopic (moisture-sensitive); therefore, the container must be kept tightly sealed in a dry environment to prevent degradation. For long-term storage, consider desiccated conditions.

Specification

Item	Specification
Appearance	White to off-white crystalline powder
Identification (IR)	Conforms to structure
Identification (HPLC)	Retention time corresponds to reference standard
Assay (HPLC)	≥ 98.0%
Chiral Purity (HPLC)	≥ 99.0% (D-isomer)
Water Content (KF)	≤ 1.0%
Residue on Ignition	≤ 0.1%

Note: Specifications can be tailored. Please contact us for the detailed technical data sheet of a specific grade.