L-Ornithyl-L-ornithine consists of two ornithine residues joined to form a functional dipeptide strongly associated with polyamine biosynthetic studies. The dual amino side chains enhance reactivity and provide high versatility for conjugation chemistry. Structural flexibility facilitates transport and metabolic pathway modeling. Use spans protein modification research, synthetic derivatization, and enzymatic mechanism exploration.
CAT No: R2425
CAS No:60259-82-7
Synonyms/Alias:L-Ornithyl-L-ornithine;60259-82-7;L-Ornithine, N2-L-ornithyl-;(2S)-5-amino-2-[[(2S)-2,5-diaminopentanoyl]amino]pentanoic Acid;H-ORN-ORN-OH;ornithyl-ornithine;Orn-Orn;CHEMBL208960;SCHEMBL9561353;DTXSID101314598;(S)-5-Amino-2-((S)-2,5-diaminopentanamido)pentanoic acid;(S)-5-Amino-2-((S)-2,5-diaminopentanamido)pentanoicacid;
L-Ornithyl-L-ornithine is a synthetic dipeptide composed of two L-ornithine residues linked by a peptide bond, representing a specialized tool in biochemical and peptide research. As a member of the peptide compound category, it serves as a model substrate for investigating peptide structure-activity relationships, enzyme specificity, and the metabolic roles of ornithine-containing sequences. Its unique composition, featuring the non-proteinogenic amino acid ornithine in both positions, enables researchers to explore the distinct physicochemical and biological properties associated with such dipeptides. The compound's relevance extends to studies of polyamine biosynthesis, peptide transporter recognition, and the design of ornithine-rich analogs for probing specific enzymatic pathways.
Peptide synthesis research: L-Ornithyl-L-ornithine is frequently employed as a reference dipeptide in the development and optimization of solid-phase peptide synthesis techniques. Its relatively simple structure and well-characterized reactivity make it an ideal candidate for benchmarking coupling efficiency, evaluating protecting group strategies, and assessing resin compatibility. Researchers utilize this dipeptide to troubleshoot synthetic protocols and to refine conditions for the assembly of more complex ornithine-containing peptides, thereby improving yield and purity in peptide production workflows.
Enzyme substrate specificity studies: As a defined dipeptide, L-Ornithyl-L-ornithine serves as a valuable substrate for investigating the specificity and catalytic mechanisms of peptidases, proteases, and aminopeptidases. Its use enables the elucidation of enzyme preferences for ornithine-rich sequences and supports kinetic analyses of hydrolysis rates. Such studies contribute to a deeper understanding of enzyme-substrate interactions, informing both basic enzymology and the rational design of enzyme inhibitors or modified substrates for biochemical research.
Transporter and uptake mechanism analysis: The compound is utilized in studies aimed at characterizing peptide transporter systems, particularly those responsible for the cellular uptake of dipeptides and oligopeptides. By tracking the absorption and intracellular fate of L-Ornithyl-L-ornithine, researchers can delineate the substrate selectivity and transport kinetics of various peptide transporters. These insights are instrumental in mapping nutrient assimilation pathways and in the development of peptide-based delivery systems for research applications.
Metabolic pathway elucidation: L-Ornithyl-L-ornithine finds application in the exploration of ornithine metabolism and its integration within broader nitrogen and polyamine biosynthetic pathways. The dipeptide can be used to trace metabolic flux, investigate the activity of ornithine-utilizing enzymes, and model the fate of ornithine derivatives in cellular systems. Such work advances knowledge of amino acid catabolism, nitrogen balance, and the regulation of polyamine synthesis in both prokaryotic and eukaryotic organisms.
Analytical method development: In the context of analytical biochemistry, L-Ornithyl-L-ornithine is employed as a standard or calibration compound for the development of chromatographic and mass spectrometric techniques targeting peptide analysis. Its defined structure and predictable behavior facilitate the validation of separation protocols, detection limits, and quantitative assays. This utility extends to quality control, method benchmarking, and the establishment of reference profiles for ornithine-containing peptides in complex biological samples.
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