N2-(1,1-Dimethylethoxy)carbonyl-N6-(phenylmethoxy)carbonyl-D-lysine
CAS 55878-47-2
CAS · 55878-47-2
Product Overview
N2-(1,1-Dimethylethoxy)carbonyl-N6-(phenylmethoxy)carbonyl-D-lysine is a high-purity amino-acids supplied for industrial and specialty chemical applications. Contact our team for specifications, packaging options and lead times.
Product Specifications
| Appearance | White powder |
|---|---|
| Purity (HPLC) | 98% min |
| TLC | 98% min |
| Melting point | 70–85 °C |
| Specific rotation [a] | +10 to +14° (C=1 in DMF) |
| Element analysis (C,H,N) | 5.0% max |
| Water (KF) | 1.0% max |
| IR spectrum | In accordance with the structure |
| Mass spectrum | In accordance with the structure |
| NMR spectrum | In accordance with the structure |
Applications
N2-(1,1-Dimethylethoxy)carbonyl-N6-(phenylmethoxy)carbonyl-D-lysine is a doubly protected D-lysine derivative widely used in peptide synthesis, medicinal chemistry, and biochemical research. The compound is designed to selectively protect both the α-amino group and the ε-amino side chain of D-lysine, enabling precise control during stepwise peptide assembly. It is commonly applied in solid-phase and solution-phase peptide synthesis for the preparation of bioactive peptides, peptidomimetics, and stereochemically defined drug candidates. This protected amino acid is also used in the synthesis of enzyme inhibitors, receptor ligands, and molecular probes where the incorporation of D-amino acids enhances metabolic stability and resistance to enzymatic degradation.
Benefits
This compound offers significant advantages due to its orthogonal protecting group strategy and high stereochemical integrity. The Boc group on the α-amino position and the benzyloxycarbonyl group on the side-chain amino group can be removed selectively under different conditions, providing excellent flexibility in multi-step synthetic routes. The use of D-lysine introduces conformational and enzymatic stability into peptides, often improving bioavailability and biological lifetime. The compound is chemically stable, compatible with standard peptide coupling reagents, and soluble in common organic solvents, allowing efficient handling, purification, and reproducibility in both research and industrial settings.
Conclusion
N2-(1,1-Dimethylethoxy)carbonyl-N6-(phenylmethoxy)carbonyl-D-lysine is a valuable protected amino acid for advanced peptide synthesis and medicinal chemistry. Its benefits, including orthogonal protection, stereochemical purity, and enhanced stability of D-amino acid incorporation, make it an essential building block for complex peptide and drug development projects. The compound continues to support innovation in peptide therapeutics, biochemical research, and chiral synthesis.
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