N-α-Z-N-β-ureido-D-2,3-diaminopropionic acid is a protected, non-proteinogenic amino acid derivative featuring a 2,3-diaminopropionic acid backbone bearing an N-β urea (ureido) functionality and an N-α benzyloxycarbonyl (Z, Cbz) protecting group. The molecule contains both amino and carboxyl functional groups, with the D stereochemical configuration specified in the product name, and the ureido side-chain provides a hydrogen-bonding and urea-based linkage motif that can participate in controlled intermolecular interactions during peptide assembly. In synthetic peptide chemistry and chemical biology workflows, the Z-protected amino acid and ureido-bearing side chain are used as a defined building block for preparing urea-linked amino acid and peptide derivatives, including labeled or structurally modified analogues for structure-activity and binding studies.
CAT No: CP05849
N-α-Z-N-β-ureido-D-2,3-diaminopropionic acid is a chiral, amino acid-derived building block featuring a D-2,3-diaminopropionic acid core with two amino functionalities and a β-ureido (urea) linkage, while the α-amino group is protected as a benzyloxycarbonyl (Z, Cbz) carbamate. The molecule contains an additional unprotected side-chain amine that can participate in selective derivatization, while the ureido carbonyl and adjacent nitrogens provide strong hydrogen-bonding and predictable reactivity under standard peptide-chemistry conditions. The Z protecting group can be removed by hydrogenolysis to reveal the α-amine for peptide coupling, and the ureido motif can act as a stable amide/urea-like handle for orthogonal functional group manipulation. The presence of multiple nitrogens and a stereogenic center makes the compound a practical chiral intermediate for constructing urea-containing peptide analogs and for preparing nitrogen-rich scaffolds used in biochemical research and industrial fine-chemical synthesis.
1. Urea-Containing Peptide Synthesis
N-α-Z-N-β-ureido-D-2,3-diaminopropionic acid supports peptide coupling strategies targeting urea-containing linkages by combining a protected α-amino group with a β-ureido functionality that can be carried through as a stable motif during chain assembly. The D-2,3-diaminopropionic stereochemistry provides a defined chiral center that can influence amide/urea geometry in the growing peptide backbone, while the unprotected side-chain amine enables controlled N-functionalization when orthogonal protection is applied. Z protection enables selective deprotection to generate an α-nucleophile for stepwise coupling, and the ureido group can participate in subsequent transformations that preserve hydrogen-bonding patterns relevant to peptidomimetic design. Downstream, the compound can be used to generate urea-bridged peptide fragments and incorporated building blocks for solid-phase or solution-phase peptide synthesis where nitrogen-rich linkers are required.
2. Chemical Biology Reagents
N-α-Z-N-β-ureido-D-2,3-diaminopropionic acid is applicable in chemical biology as a nitrogen-rich amino acid analog for probing molecular recognition, protein-ligand interactions, and enzyme active-site preferences involving urea or urea-like hydrogen-bond donors/acceptors. The ureido carbonyl and adjacent nitrogens provide a structured hydrogen-bonding array that can be used to tune binding interactions in structure-activity relationship studies without relying solely on hydrophobic contacts. The D-configuration and the presence of an orthogonally removable Z-protected α-amine allow preparation of defined conjugation handles, including side-chain functionalization for attaching probes, affinity tags, or reporter groups. The resulting derivatives can serve as biochemical research intermediates for generating labeled peptidomimetics and for mapping interaction motifs in protein engineering and chemical probe development workflows.
3. Protected Amino Acid Intermediate
N-α-Z-N-β-ureido-D-2,3-diaminopropionic acid functions as a protected amino acid intermediate for manufacturing-grade synthesis of complex nitrogen-containing building blocks and peptidomimetic fragments. The Z (Cbz) carbamate provides a robust α-amino protection strategy that is compatible with common peptide coupling conditions and can be selectively removed to expose the α-nucleophile when assembling higher-order structures. The β-ureido group offers a chemically stable urea linkage that can withstand many coupling and protection steps, while the additional free amine can be temporarily protected or functionalized to manage chemoselectivity. The compound's multi-nitrogen architecture makes it suitable for process chemistry routes that require orthogonal control over amino reactivity, enabling consistent preparation of chiral intermediates for specialty chemical production and fine chemical synthesis.
4. Peptidomimetics And SAR Studies
N-α-Z-N-β-ureido-D-2,3-diaminopropionic acid can be employed in peptidomimetic construction for SAR studies where urea-containing scaffolds are used to reproduce constrained hydrogen-bonding patterns typical of bioactive peptide interfaces. The ureido functionality provides a predictable donor/acceptor arrangement that can be incorporated into analogs to modulate binding selectivity while the D-2,3-diaminopropionic stereocenter supports stereochemically defined conformational preferences. The Z-protected α-amine and the side-chain amine enable stepwise derivatization, including installation of N-substituents or conversion to additional coupling partners for generating libraries of analogs. The resulting urea-bearing chiral derivatives can be used as fragment-like building blocks in molecular design and medicinal chemistry research pipelines focused on structure-function relationships.
5. Bioconjugation Chemistry
N-α-Z-N-β-ureido-D-2,3-diaminopropionic acid supports bioconjugation workflows by providing a protected α-amine that can be deprotected to generate a controlled nucleophile for coupling to activated surfaces, linkers, or biomolecule-reactive groups. The ureido group contributes strong hydrogen-bonding character that can influence local solvation and spacing of conjugated motifs, which is relevant when constructing peptide-based linkers or urea-containing attachment handles. The free side-chain amine can be used for orthogonal functionalization to introduce solubilizing groups, affinity tags, or cleavable linkers, supporting chemoselective conjugation designs. Downstream, the compound-derived conjugates can serve as biochemical research intermediate materials for preparing labeled peptides, probe constructs, and biomolecule-modified reagents used in analytical research and chemical biology studies.
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