Boc-L-Orn(pyrazinylcarbonyl)-OH is a Boc-protected, L-ornithine-derived amino acid derivative in which the side-chain amine is acylated with a pyrazinylcarbonyl group, yielding a modified, non-proteinogenic functionalized building block for peptide chemistry. The molecule contains a Boc carbamate protecting group on the α-amino functionality, a free carboxylic acid (-CO2H), and a side-chain carbonyl linked to a pyrazine ring that provides a heteroaromatic nitrogen-rich motif for hydrogen-bonding and coordination behavior. In synthesis, this protected amino acid is used as a precursor for introducing the pyrazinylcarbonyl-modified ornithine residue into peptide structures via stepwise coupling while the Boc group helps control chemoselectivity of amide bond formation at the α-amino terminus.
CAT No: CP25565
CAS No:201046-36-8
Synonyms/Alias:BOC-ORN(PYRAZINYLCARBONYL)-OH;201046-36-8;AmbotzBAA1198;AC1ODTVA;Boc-L-Orn(pyrazinylcarbonyl)-OH;CTK0J9689;MolPort-000-001-614;C15H22N4O5;ZINC2567620;6427AH;Boc-L-S-pyrazinylcarbonyl-L-ornithine;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(pyrazine-2-carbonylamino)pentanoicAcid;RT-011776;B53117;K-5877;L-Ornithine,N2-[(1,1-dimethylethoxy)carbonyl]-N5-(pyrazinylcarbonyl)-(9CI)
Chemical Name:N-alpha-t-Butyloxycarbonyl-N-delta-pyrazinylcarbonyl-L-ornithine
Boc-L-Orn(pyrazinylcarbonyl)-OH is a Boc-protected L-ornithine derivative bearing a pyrazinylcarbonyl functional group on the side chain, designed as a protected amino acid building block for peptide and peptidomimetic synthesis. The Boc group provides a stable N-terminal protection strategy for controlled coupling, while the pyrazinylcarbonyl moiety introduces a heteroaromatic, carbonyl-containing functionality that can be carried through as part of a defined side-chain motif in downstream constructs. This reagent is typically selected when a protected ornithine unit with an appended pyrazine-containing carbonyl group is required for library synthesis, SAR-focused analog generation, or medicinal chemistry scaffold elaboration.
1. Peptide Library Building
Boc-L-Orn(pyrazinylcarbonyl)-OH is used by peptide chemistry groups to construct sequence-defined libraries where an ornithine-derived side-chain is required to present a pyrazine-containing carbonyl motif. The Boc protection enables routine coupling workflows for assembling protected segments into longer peptides or peptidomimetic backbones, while the heteroaromatic pyrazinylcarbonyl functionality supports the generation of analog series for structure-activity relationship studies. This building block is especially useful when researchers need to keep the side-chain functionality intact through multiple synthetic steps and incorporate it at a specific position within a peptide scaffold.
2. Medicinal Chemistry Scaffold Development
Boc-L-Orn(pyrazinylcarbonyl)-OH serves as a medicinal chemistry intermediate for preparing peptidomimetic and constrained amide-containing structures that incorporate a pyrazine-derived carbonyl group as a pharmacophore element. Medicinal chemistry teams use this type of protected amino acid derivative to rapidly generate analogs with defined heteroaromatic substitution patterns, supporting SAR campaigns that rely on systematic variation of side-chain electronics and hydrogen-bonding features. The Boc-protected amino acid format streamlines integration into larger synthetic sequences where precise functional-group presentation is required for subsequent derivatization or final coupling steps.
3. Protected Amide-Functional Intermediate Synthesis
Boc-L-Orn(pyrazinylcarbonyl)-OH is commonly employed as a protected intermediate when the goal is to introduce a pyrazinylcarbonyl-bearing ornithine side chain into complex molecules without premature loss or modification of the appended carbonyl/heteroaromatic functionality. Process and development chemists use this reagent to prepare well-defined, isolable building blocks that can be carried forward into downstream condensations, segment couplings, or final assembly of multi-functional targets. The combination of N-terminal Boc protection and the stable carbonyl-bearing pyrazine substituent makes it a practical choice for constructing intermediates that require controlled reactivity during stepwise synthesis.
4. Structure-Activity Analogue Generation
Boc-L-Orn(pyrazinylcarbonyl)-OH is used in research settings to generate analogs that preserve a specific ornithine-derived side-chain architecture while varying the surrounding peptide context. Chemical biology and medicinal chemistry teams often rely on such building blocks to probe how a heteroaromatic pyrazinylcarbonyl group influences binding-relevant features like shape complementarity and hydrogen-bonding patterns within peptide-like scaffolds. By incorporating this protected ornithine derivative at a defined position, researchers can produce structurally consistent series that support comparative evaluation of structure-function relationships during lead optimization.
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