Nalpha-fmoc-ndelta-trityl-l-ornithine is a doubly protected ornithine derivative used to install branching or reactive side-chain functionalities. The trityl group enables controlled deprotection for downstream modifications. Researchers use it in cyclic peptide synthesis and structure-guided design. Its versatility supports complex peptide assembly.
CAT No: R2132
CAS No:1998701-26-0
Synonyms/Alias:1998701-26-0;Fmoc-Orn(Trt)-OH;Nalpha-fmoc-ndelta-trityl-l-ornithine;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-(tritylamino)pentanoic acid;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tritylamino)pentanoic acid;DTXSID501153417;MFCD30478737;N-alpha-Fmoc-N-delta-trityl-L-Ornithine;AS-83863;E70922;N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N5-(triphenylmethyl)-L-ornithine;(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-5-[(triphenylmethyl)amino]pentanoic acid;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5-[(triphenylmethyl)amino]pentanoic acid;
Nalpha-Fmoc-Ndelta-trityl-L-ornithine is a protected derivative of the naturally occurring amino acid L-ornithine, engineered for specialized use in peptide synthesis and biochemical research. Featuring an N-terminal 9-fluorenylmethyloxycarbonyl (Fmoc) group and a delta-amino trityl protecting group, this compound offers dual protection that facilitates selective deprotection strategies during solid-phase peptide synthesis (SPPS). The unique combination of protecting groups on the ornithine scaffold allows researchers to precisely manipulate the orthogonality and sequence incorporation of ornithine residues in complex peptide constructs. Its utility extends to a variety of research applications where site-specific functionalization and controlled side-chain reactivity are required, making it a valuable building block for advanced peptide chemistry.
Peptide Synthesis: Widely employed in SPPS protocols, the protected ornithine derivative enables the incorporation of ornithine residues with high fidelity into synthetic peptides. The Fmoc group on the alpha-amino terminus provides compatibility with standard Fmoc-based synthesis strategies, while the trityl protection on the delta-amino group prevents undesired side reactions or premature functionalization. This orthogonal protection scheme is particularly advantageous for the stepwise assembly of peptides containing multiple reactive side chains, ensuring efficient chain elongation and minimizing byproduct formation.
Site-Specific Modification: The dual protection offered by Fmoc and trityl groups allows for selective deprotection of either the alpha- or delta-amino functionalities at desired stages of synthesis. This feature is essential for the introduction of post-synthetic modifications, such as conjugation of fluorescent probes, attachment of affinity tags, or installation of cross-linkers at precise positions within a peptide sequence. Such controlled modifications are critical for generating peptide-based probes, molecular tools, and biomaterials with tailored properties for biochemical and biophysical studies.
Structure-Activity Relationship Studies: Incorporation of ornithine residues with protected side chains supports systematic investigation of peptide structure and function. By enabling the selective exposure or masking of the delta-amino group, researchers can probe the role of ornithine in modulating peptide conformation, receptor binding, or enzymatic recognition. This approach is instrumental in the design and optimization of bioactive peptides, peptidomimetics, and enzyme substrates for fundamental and applied research.
Combinatorial Library Construction: The use of orthogonally protected amino acid derivatives such as this one is pivotal in the generation of diverse peptide libraries for high-throughput screening applications. The ability to control side-chain reactivity facilitates the synthesis of highly diverse peptide sequences, which can be screened for novel biological activities, binding affinities, or pharmacological properties. This strategy accelerates the discovery of lead compounds and functional motifs in peptide-based drug discovery and molecular recognition studies.
Analytical Method Development: The protected ornithine derivative also serves as a reference standard or calibration compound in the development and validation of analytical methods for peptide analysis. Its defined chemical structure and predictable deprotection behavior make it suitable for optimizing chromatographic separations, mass spectrometric detection, and purity assessments of synthetic peptides. Reliable analytical performance is essential for quality control and characterization in peptide production workflows.
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