Cbz-L-Homocitrulline is a Cbz-protected, L-configured amino acid derivative featuring the homocitrulline backbone with an amino acid α-center and a side chain bearing an additional methylene relative to citrulline, along with a ureido-type functionality. The molecule contains both an α-amino group and a carboxyl group masked as a protected amino acid (with the benzyloxycarbonyl, Cbz, group on the amino functionality), while the ureido/amide-like side-chain moiety provides hydrogen-bonding and polar interaction sites that can be carried into peptide frameworks. In peptide chemistry, Cbz-L-homocitrulline is employed as a protected building block for incorporating homocitrulline residues into peptide or peptidomimetic sequences for structure-activity studies, chemical biology labeling strategies, or analytical method development involving defined amino acid side-chain chemistries.
CAT No: CP06208
Cbz-L-Homocitrulline is an L-homolog of citrulline bearing an N-Cbz (benzyloxycarbonyl) carbamate on the amino group and a side-chain urea functionality that is well suited to peptide and urea chemistry. The molecule contains a stereogenic center at the alpha carbon, with the L-configuration governing downstream stereochemical outcomes in peptide coupling and side-chain transformations. The protected amine and the urea-derived carbonyl/amide pattern provide defined hydrogen-bonding and controlled reactivity, while the Cbz group enables orthogonal protection strategies relative to other nucleophiles. As a chiral amino acid derivative, Cbz-L-Homocitrulline functions as a protected amino acid intermediate for building urea-containing motifs and for preparing further substituted homocitrulline analogs used in synthetic and biochemical studies.
1. Peptide Synthesis
Cbz-L-Homocitrulline is applied in peptide synthesis workflows where urea-bearing amino acid units are incorporated into peptide backbones or used as side-chain functional handles. The Cbz-protected alpha-amino group supports standard peptide coupling chemistry after deprotection or activation to generate the corresponding reactive amino component, while the homocitrulline side chain provides a urea motif that can participate in hydrogen-bonding and conformational effects. The stereogenic L-center helps maintain stereochemical fidelity during coupling and subsequent manipulations, which is critical when preparing stereochemically defined peptide building blocks. Downstream, the urea functionality can be retained for receptor-binding studies or modified to generate peptide analogs with altered polarity and recognition profiles, making the compound suitable for structured peptide library construction and method development in amino acid chemistry.
2. Urea-Containing Analog Design
Cbz-L-Homocitrulline is used in molecular design and SAR-focused synthesis of urea-containing peptidomimetics and constrained analogs. The side-chain urea pattern provides a functional group array that can be derivatized through controlled N-alkylation, N-acylation, or conversion to alternative urea/guanidinium-like motifs, enabling systematic tuning of charge distribution and hydrogen-bond donor/acceptor counts. The Cbz carbamate serves as a removable protecting group that can be selectively cleared to expose the amino functionality when building analogs that require orthogonal protection relative to other reactive groups. The resulting derivatives can be used as fragment-like scaffolds or as side-chain-modified amino acid units for generating focused libraries, supporting structure-function investigations and synthetic route planning in fine chemical synthesis.
3. Protected Amino Acid Chemistry
Cbz-L-Homocitrulline is suitable for protected amino acid synthesis strategies that rely on orthogonal deprotection and predictable functional group behavior. The N-Cbz group provides a stable carbamate protecting group on the alpha-amino functionality, allowing the compound to be handled and coupled under conditions compatible with urea-derived side-chain chemistry. The alpha-carboxylate and protected amine arrangement enables conversion into activated intermediates for peptide building block preparation, while the L-stereocenter supports stereoselective assembly of chiral sequences. Selective deprotection of the Cbz group can generate a free amino intermediate for subsequent coupling, conjugation, or derivatization, supporting downstream preparation of homocitrulline-containing peptides and urea-functional biochemical probes.
4. Chemical Biology Probes
Cbz-L-Homocitrulline is applied in chemical biology research where urea-containing amino acid motifs are incorporated into labeling reagents, affinity handles, or enzyme-interaction probes. The urea side chain can support specific noncovalent interactions through hydrogen bonding, and the protected amine allows controlled introduction into larger molecular frameworks without premature side reactions. The defined L-configuration helps preserve stereochemical recognition features when the probe is integrated into peptides or peptidomimetic constructs used for mechanistic studies. After appropriate functional group unveiling and downstream coupling, the compound can serve as a biochemical research intermediate for generating labeled or modified biomolecule fragments that interrogate binding interfaces and substrate-like recognition patterns.
5. Pharmaceutical Intermediate Preparation
Cbz-L-Homocitrulline is relevant to pharmaceutical intermediate preparation and process chemistry for manufacturing urea-containing amino acid derivatives used in medicinal chemistry programs. The Cbz-protected amino group and the urea-bearing side chain provide a chemically tractable platform for conversion into activated derivatives, protected intermediates, or side-chain-modified analogs that can be carried through multi-step synthesis. The stereochemical integrity of the L-center supports consistent product profiles in downstream coupling steps, especially when preparing chiral building blocks for peptide-like or peptidomimetic candidates. The compound's functional group complement enables integration into industrial fine chemical synthesis routes where orthogonal protection and controlled reactivity are required for reliable intermediate generation and scalable derivatization.
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