CAS · 88568-95-0
Product Overview
N-Cbz-2-Phosphonoglycine trimethyl ester is a high-purity pharmaceutical-intermediates supplied for industrial and specialty chemical applications. Contact our team for specifications, packaging options and lead times.
Product Specifications
| Appearance: | Off-White to white solid |
|---|---|
| HNMR: | Confirms to structure |
| Purity (HPLC): | 98% min |
| Water: | 0.5% max |
Applications
1. Peptide and Peptidomimetic Synthesis
Used as a protected glycine analog containing a phosphonate moiety.
Allows incorporation of phosphonic acid bioisosteres in peptide chains, useful in drug development.
Often applied in the synthesis of:
Phosphonopeptides
Enzyme inhibitors
Peptide mimics with enhanced metabolic stability
2. Medicinal Chemistry & Drug Design
Serves as a bioisostere for phosphate or carboxyl groups.
Frequently used in the design of inhibitors targeting:
Aminopeptidases
Proteases
Other enzymes interacting with phosphorylated substrates
Valuable in developing anti-tumor, antiviral, or antibacterial agents.
3. Prodrug and Bioconjugation Research
The trimethyl ester form enhances lipophilicity, making it easier to cross cell membranes.
Ester groups can be selectively hydrolyzed under physiological conditions, releasing the active phosphonic acid form intracellularly - a classic prodrug strategy.
4. Organic Synthesis Intermediate
Functions as a versatile intermediate for preparing:
Modified amino acids
Functionalized phosphonic acid derivatives
Complex chiral ligands or catalysts
Useful for generating chiral building blocks for asymmetric synthesis.
Benefits
1. Dual Protection Strategy
Cbz group protects the amino function, allowing selective deprotection under mild hydrogenolysis.
Trimethyl ester masking of the phosphonic acid allows easier handling, better solubility in organic solvents, and delayed reactivity - facilitating multi-step synthesis.
2. Enhanced Lipophilicity
Trimethyl ester increases hydrophobicity, which improves:
Cell permeability
Membrane transport
Solubility in organic media
Beneficial in both biological evaluation and drug formulation.
3. Stable and Easy to Handle
Stable under typical storage conditions.
Compatible with common peptide coupling methods (e.g., EDC/HOBt, DCC, etc.).
Well-suited for solution-phase or solid-phase synthesis.
4. Structural Versatility
Combines an amino acid core with a phosphonate moiety, allowing diverse chemical transformations, including:
Hydrolysis
Coupling
Oxidation/reduction
Rearrangement or ring-closing reactions
Conclusion
N-Cbz-2-Phosphonoglycine Trimethyl Ester (CAS 88568-95-0) is a specialized amino acid derivative featuring phosphonic acid functionality and Cbz/ester protection. It is primarily used in peptide synthesis, drug discovery, and prodrug design, where it acts as a stable, lipophilic, and reactive intermediate. Its ability to mimic phosphate groups while retaining peptide compatibility makes it a valuable compound in enzyme inhibitor development, phosphopeptide analog synthesis, and medicinal chemistry applications.
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