N-α-Z-N-β-ureido-L-2,3-diaminopropionic ac contains an α-amino acid backbone bearing an N-α benzyloxycarbonyl (Z, Cbz) protecting group and a β-ureido substituent, classifying it as a protected, ureido-functional amino acid derivative. The molecule includes an α-carboxyl group and an α-amino nitrogen masked as a carbamate, while the β-ureido moiety provides a urea linkage with hydrogen-bonding and carbonyl functionality that can participate in selective coupling and downstream derivatization. In peptide and peptidomimetic synthesis contexts, the Z protection supports chemoselective handling of the α-amino functionality, and the ureido side-chain offers a defined polar handle for preparing structured amino acid building blocks used in solution-phase or solid-phase assembly and in structure-activity or chemical-biology studies requiring controlled side-chain functionality.
CAT No: CP05850
N-α-Z-N-β-ureido-L-2,3-diaminopropionic ac is a chiral amino acid derivative featuring an L-configured 2,3-diaminopropionic acid backbone and a β-ureido functionality that can participate in hydrogen-bonding and amide-like reactivity. The N-α position bears a benzyloxycarbonyl (Z, Cbz) protecting group, enabling controlled peptide coupling chemistry while suppressing undesired side reactions from the α-amino site. The molecule contains multiple nitrogen atoms (α- and β-ureido nitrogens) and a carboxylate handle, which together support derivatization into protected amino acid building blocks and subsequent conversion into urea-containing peptide motifs. The combination of a stereogenic center, a ureido group, and an N-protecting group makes the compound a structurally defined intermediate for peptide science, chiral synthesis, and downstream functional group transformations.
1. Urea-Containing Peptide Synthesis
N-α-Z-N-β-ureido-L-2,3-diaminopropionic ac is used in peptide synthesis workflows that require urea-linked motifs, where the β-ureido group functions as a hydrogen-bonding element and a defined nitrogen donor/acceptor pattern. The Z-protected α-amino functionality supports selective activation and coupling at the intended N-terminus while reducing competitive reactions from the ureido nitrogens. The carboxyl group can be converted into activated derivatives compatible with standard peptide coupling strategies, enabling incorporation into peptide chains as a chiral building block. Resulting urea-containing peptide analogs can be applied to structure-activity relationship studies, scaffold diversification, and synthetic methodology development in peptide chemistry.
2. Protected Amino Acid Intermediate
N-α-Z-N-β-ureido-L-2,3-diaminopropionic ac serves as a protected amino acid intermediate for controlled N-protection management during multi-step synthesis. The Z (Cbz) group provides a removable α-amino protection handle, supporting orthogonal deprotection sequences that can be matched to ureido stability and subsequent coupling requirements. The ureido functionality can be retained through protection/deprotection cycles, enabling stepwise construction of urea-bearing intermediates and later conversion into peptide-grade building blocks. Downstream utility includes preparation of protected amino acid derivatives for fine chemical synthesis and chiral intermediate supply in process chemistry routes that require reproducible functional group positioning.
3. Chemical Biology And Protein Engineering
N-α-Z-N-β-ureido-L-2,3-diaminopropionic ac can be incorporated into chemical biology and protein engineering strategies that require defined urea-containing residues to tune molecular recognition. The β-ureido group contributes directional hydrogen-bonding interactions that can influence binding-site geometry when introduced into peptide segments or protein-mimetic constructs. The L-stereochemistry of the 2,3-diaminopropionic acid backbone supports stereochemically consistent incorporation, which is relevant for generating stereodefined analogs used in biochemical investigations. The protected α-amino site enables controlled assembly into longer constructs, supporting downstream labeling, conjugation-ready intermediate preparation, and comparative studies of modified biomolecular interfaces.
4. Peptidomimetics And SAR Studies
N-α-Z-N-β-ureido-L-2,3-diaminopropionic ac is applicable to peptidomimetic construction where urea linkages are used to emulate key polar interactions of peptide backbones. The ureido group and multiple nitrogen atoms provide a scaffold for modulating solubility, conformational preferences, and hydrogen-bonding networks in analog series. Z-protection at the α-amino position supports sequential functionalization and coupling, enabling systematic variation of chain length and side-chain context while maintaining stereochemical integrity. The resulting urea-containing peptidomimetics can be used as defined chemical probes for structure-activity relationship studies and fragment-based molecular design programs.
5. Pharmaceutical Intermediate Preparation
N-α-Z-N-β-ureido-L-2,3-diaminopropionic ac is suitable for pharmaceutical intermediate preparation in manufacturing-oriented synthesis planning that targets urea-bearing amino acid derivatives. The protected α-amino group (Z) supports controlled chemoselectivity during upstream synthesis steps, aligning with process chemistry needs for minimizing side reactions and maintaining consistent intermediate quality. The ureido functionality can be carried through as a stable polar group during route design, then used for downstream transformations into peptide-like intermediates or urea-containing fragments. The compound's defined chiral center and protected functional group arrangement make it a practical input for specialty chemical production where amino acid derivatization and protected building block supply are central to scalable synthesis.
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