Overview
D-Histidine Methyl Ester is the methyl ester derivative of D-histidine, a non-proteinogenic enantiomer of the amino acid histidine. It serves as a versatile chiral synthon in organic and medicinal chemistry, particularly for constructing histidine-containing peptides or metal-binding ligands. Unlike its L-isomer, D-histidine derivatives are less common in nature but valuable for designing enzyme inhibitors or probes targeting specific stereochemical interactions. The esterification enhances solubility and reactivity for coupling reactions in solid-phase peptide synthesis (SPPS).
Physical and Chemical Properties
The compound exhibits typical amino acid ester characteristics, including zwitterionic behavior in aqueous solutions and sensitivity to hydrolysis under acidic/basic conditions. Its imidazole ring enables metal coordination, useful in catalysis. Thermal stability is moderate, with decomposition observed near 200°C. Spectroscopic data (e.g., NMR, IR) align with its structure, showing peaks for ester carbonyl (∼1740 cm⁻¹) and imidazole protons (∼7-8 ppm). Optical rotation values ([α]D) vary by solvent but are critical for confirming enantiomeric purity.
Main Applications
In pharmaceuticals, D-Histidine Methyl Ester is employed to synthesize chiral histidine analogs for drug candidates, such as protease inhibitors or radiopharmaceuticals. Its metal-binding capacity aids in designing catalytic antibodies. Biochemically, it’s used to study enzyme stereospecificity or modify peptide properties (e.g., stability, bioavailability). Niche applications include asymmetric synthesis auxiliaries and diagnostic reagent development.
Safety and Storage
As a fine chemical, handling requires standard lab precautions: gloves, goggles, and fume hoods. It’s non-flammable but may irritate eyes/skin. Spills should be neutralized with dilute acid or base. Long-term storage demands moisture-proof packaging under inert gas (argon/nitrogen) to prevent racemization or ester hydrolysis. Shelf life typically exceeds 2 years when stored correctly at 2-8°C.
B2B Procurement Guide
Bulk purchases for industrial use should prioritize suppliers with GMP compliance if intended for APIs. Key specifications include enantiomeric excess (ee ≥98%), residual solvent levels, and microbial limits. Request batch-specific COAs with HPLC/GC-MS data. Spot-check identity via FTIR or chiral HPLC. For research-scale orders, consider distributors like Sigma-Aldrich or TCI, while contract manufacturers (e.g., Chinese API producers) offer competitive kilo-scale pricing.
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