Bz-Cit-OMe is a benzoyl-protected citrulline derivative in which the α-amino group is acylated as a benzamide (Bz) and the carboxyl group is converted to a methyl ester (OMe), yielding a protected amino acid ester rather than a free amino acid. The side chain retains the ureido functionality characteristic of citrulline, while the molecule bears both an amide linkage and an ester carbonyl, with stereochemistry not specified in the product name. Bz-Cit-OMe is used as a chemically protected building block for peptide and amide bond construction, including incorporation of citrulline-like side-chain chemistry into synthetic sequences and preparation of labeled or functionalized citrulline-containing intermediates for biochemical and structure-activity studies.
Bz-Cit-OMe is a methyl ester derivative of citrulline bearing an N-benzoyl (Bz) protecting group on the α-amino function, yielding a chiral amino acid ester with a ureido-containing side chain. The structure combines an N-acylated amide (benzamide) that suppresses unprotected amine reactivity with an esterified carboxylate (OMe) that can participate in acyl-transfer and peptide-coupling workflows after activation. The ureido moiety presents strong hydrogen-bonding functionality and can be used as a handle for further derivatization or for incorporation into peptide-like frameworks where side-chain recognition matters. Stereochemical integrity of the citrulline center and the orthogonality between N-protection and ester reactivity make Bz-Cit-OMe a practical chiral intermediate for protected amino acid synthesis and downstream peptide construction.
1. Protected Amino Acid Synthesis
Bz-Cit-OMe is applied in protected amino acid synthesis and chiral intermediate preparation for workflows that require controlled reactivity of the citrulline side chain and backbone. The N-benzoyl group masks the α-amino functionality, enabling selective handling of the ureido side chain and reducing side reactions during ester activation or coupling chemistry. The methyl ester form supports conversion into activated carboxyl derivatives for peptide building block preparation while maintaining stereochemical fidelity at the α-carbon. Downstream, the compound can be routed into N-protected citrulline residues for stepwise assembly of peptide segments and for generating defined intermediates used in synthetic organic chemistry.
2. Peptide Coupling Chemistry
Bz-Cit-OMe is suitable for peptide coupling chemistry where a citrulline residue must be incorporated under conditions compatible with N-protected amino acids. The benzoyl-protected amine provides a stable N-acyl handle that can withstand common coupling conditions, while the ester functionality can be transformed into coupling-ready carboxyl equivalents to form amide bonds. The ureido side chain contributes additional hydrogen-bonding interactions that can influence coupling outcomes, solubility, and conformational preferences in peptide analogs. Peptide building block preparation from Bz-Cit-OMe supports construction of citrulline-containing sequences used for biochemical research intermediate generation and synthetic methodology development.
3. Peptidomimetics And SAR Studies
Bz-Cit-OMe is used in peptidomimetic construction and structure-activity relationship studies that require citrulline-like functionality embedded in constrained scaffolds. The ureido group can serve as a pharmacophore-like element for molecular recognition, while the protected backbone enables controlled elaboration into analogs with modified termini or side-chain substituents. The N-benzoyl protection strategy supports stepwise functional group manipulation, including conversion of the ester into amide-linked derivatives and subsequent transformations of the ureido environment when designing analog series. Resulting citrulline-based intermediates can be employed to generate libraries of peptide analogs for SAR-focused synthesis and fragment-based molecular design.
4. Chemical Biology Labeling
Bz-Cit-OMe can be applied to chemical biology labeling strategies that rely on citrulline side-chain chemistry for conjugation-ready intermediates. The ureido functionality provides a functional motif that can be carried through protected amino acid stages and later converted into conjugation-compatible derivatives depending on the chosen chemoselective transformation. The N-benzoyl and methyl ester pattern helps manage orthogonality, allowing selective deprotection or activation steps that expose specific reactive sites for downstream attachment to biomolecule scaffolds. Citrulline-containing derivatives derived from Bz-Cit-OMe can therefore serve as intermediates for biomolecule modification workflows and for generating defined probes used in biochemical investigations.
5. Process Chemistry Intermediate
Bz-Cit-OMe is relevant to process chemistry and specialty chemical production as a chiral amino acid ester intermediate with protecting-group control over amine reactivity. The benzoyl-protected α-amino group and the methyl ester provide a predictable reactivity profile that can be integrated into manufacturing routes for protected amino acid derivatives and peptide building blocks. The compound's functional-group arrangement supports sequential transformations, such as activation of the ester portion for coupling or conversion into downstream protected intermediates while limiting undesired side reactions from the amine. Bz-Cit-OMe thus functions as a practical intermediate for fine chemical synthesis where stereochemical consistency and orthogonal protection strategies are required for scalable peptide-related manufacturing.
3. Emu oil in combination with other active ingredients for treating skin imperfections
5. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis
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