Benzyloxycarbonyl-alpha-phosphonoglycine trimethyl ester

Benzyloxycarbonyl-α-phosphonoglycine trimethyl ester (CAS 88568-95-0) is a strategically engineered phosphonate amino acid derivative designed for peptide mimetic development and transition-state analog research. This molecule integrates three orthogonal functional modules: a Cbz (benzyloxycarbonyl) protecting group enabling selective amine deprotection via hydrogenolysis, a phosphonate moiety at the α-carbon that mimics phosphate transition states with enhanced metabolic stability, and a trimethyl ester configuration that balances lipophilicity for improved membrane permeability. The phosphonate group—structurally analogous to phosphate but resistant to phosphatase cleavage—positions this intermediate as a privileged scaffold for protease inhibitor design, prodrug systems, and phosphonopeptide therapeutics targeting metalloenzymes. Manufactured under controlled conditions, it supports medicinal chemistry programs where phosphate mimicry is critical for binding affinity in kinase pathways, viral proteases, and bone metabolism modulators.

Property

Product Name	Benzyloxycarbonyl-α-phosphonoglycine trimethyl ester
CAS Number	88568-95-0
Chinese Name	苄氧羰基-α-膦酰基甘氨酸三甲酯
Synonyms	Cbz-α-phosphonoglycine trimethyl ester; Z-α-phosphonoglycine trimethyl ester; MFCD02685914
Chinese Synonyms	Cbz-α-膦酰甘氨酸三甲酯; Z-α-膦酰基甘氨酸三甲酯; 苄氧羰基氨基膦酰乙酸甲酯; 膦酰氨基酸衍生物
Molecular Formula	C₁₃H₁₈NO₇P
Molecular Weight	331.26 g/mol
Purity	≥ 98% (HPLC area normalization)
Product Category	Pharmaceutical Intermediates / Phosphonate Amino Acids / Protected Building Blocks
Appearance	White to Off-white Crystalline Powder
Storage Conditions	Store in a cool, dry, well-ventilated area away from light and moisture. Keep container tightly closed under inert atmosphere (nitrogen or argon). Protect from strong acids/bases to avoid ester hydrolysis or premature Cbz deprotection.
Shelf Life	18-24 months under recommended storage conditions
Packaging	100mg/vial, 500mg/vial, 1g/bottle, 5g/bottle, or customized according to customer requirements
Applications	Phosphonopeptide synthesis, protease inhibitor development, prodrug design, transition-state analog research, metalloenzyme targeting, kinase pathway modulation, antiviral drug intermediates, bone resorption inhibitor precursors
Reactivity	Suitable for selective Cbz deprotection (catalytic hydrogenolysis), phosphonate ester hydrolysis to mono/di-acid forms, amide coupling at the carboxylate, phosphonate-directed metal coordination, and orthogonal deprotection strategies
Special Note	✅ Moisture-sensitive phosphonate ester—handle under inert atmosphere. Orthogonal deprotection: Cbz removable via H₂/Pd-C, methyl esters via controlled hydrolysis. Part of our phosphonate building block series.