(S)-2-(((Benzyloxy)carbonyl)amino)-3,3-dicyclopropylpropanoic acid

(S)-2-(((Benzyloxy)carbonyl)amino)-3,3-dicyclopropylpropanoic acid is a specialized Cbz-protected chiral building block for pharmaceutical peptide synthesis and drug discovery. As the Cbz-protected derivative of 3,3-dicyclopropylalanine, (S)-2-(((Benzyloxy)carbonyl)amino)-3,3-dicyclopropylpropanoic acid offers an orthogonal protecting group strategy complementary to Boc-protected amino acids. The Cbz group is removed under mild hydrogenation conditions, making (S)-2-(((Benzyloxy)carbonyl)amino)-3,3-dicyclopropylpropanoic acid particularly valuable for synthetic sequences where acidic deprotection (required for Boc removal) would be incompatible with other functionalities. The rigid dicyclopropyl scaffold has been shown to deliver potent and metabolically stable compounds in drug discovery programs, and (S)-2-(((Benzyloxy)carbonyl)amino)-3,3-dicyclopropylpropanoic acid provides researchers with a versatile entry point to this valuable pharmacophore.

Product Parameters

Quality Assurance at Cosperpharm

 Gas chromatography (GC) – purity ≥97.0%

 Non‑aqueous titration – purity ≥97.0%

 Refractive index – confirmatory analysis

 ¹H NMR – structural verification

 Appearance – colorless to light yellow to light orange clear liquid

A comprehensive COA, MSDS (with full GHS information), and certificate of origin accompany every shipment.

Product Advantages

(S)-2-(((Benzyloxy)carbonyl)amino)-3,3-dicyclopropylpropanoic acid provides the (S)-configured enantiomer of this sterically hindered amino acid, ensuring that the chirality of your target molecule is established from the earliest synthetic step.

Cbz Protecting Group for Hydrogenation Deprotection

The benzyloxycarbonyl (Cbz) group offers orthogonal deprotection under hydrogenation conditions (H₂/Pd-C), allowing selective removal of the N-terminal protection without affecting acid-labile or base-labile functionalities. This makes (S)-2-(((Benzyloxy)carbonyl)amino)-3,3-dicyclopropylpropanoic acid complementary to Boc- and Fmoc-protected amino acids in complex synthetic sequences.

 Dicyclopropyl Scaffold for Enhanced Metabolic Stability

The geminal dicyclopropyl substitution at the β-position introduces significant steric bulk that protects adjacent amide bonds from enzymatic hydrolysis. This structural feature has been shown to deliver potent and metabolically stable compounds in drug discovery.

 Optimized Lipophilicity for Efficient Synthesis

With a calculated LogP of 2.80, (S)-2-(((Benzyloxy)carbonyl)amino)-3,3-dicyclopropylpropanoic acid offers balanced lipophilicity for efficient extraction, chromatographic purification, and coupling reactions.

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