4-Nitro-Z-D-Arg-OH contains a D-configured arginine backbone bearing a 4-nitro substituent on the side-chain aromatic guanidino system and a Z-protecting group on the amino functionality, with both an amino acid α-amino group and a carboxylic acid present in the protected molecule. The guanidino-containing side chain provides strong basic character and hydrogen-bonding capacity, while the 4-nitro group introduces an electron-withdrawing functionality that can modulate side-chain electronics and reactivity; the Z group functions as an amino protecting group to control chemoselectivity and suppress undesired side reactions during derivatization. As a protected, structurally modified amino acid derivative, it is employed as a substrate precursor in peptide synthesis workflows and in chemical biology or analytical studies where a nitro-functionalized arginine analogue is used to probe structure-reactivity relationships, labeling strategies, or side-chain modification effects.
CAT No: CP26629
CAS No:200188-53-0
Synonyms/Alias:4-NITRO-Z-D-ARG-OH;ZINC2560763;200188-53-0
4-Nitro-Z-D-Arg-OH is a D-configured arginine derivative bearing a Z-protecting group and a 4-nitro substituent on the side-chain aromatic system, combining guanidinium-like functionality with a strongly electron-withdrawing nitro group that supports downstream chemical handling and analytical discrimination. This protected amino acid building block is commonly selected when a controlled arginine side-chain chemistry is required for peptide assembly or for the preparation of specialized arginine-containing intermediates where side-chain electronics and protection strategy matter.
1. Peptide Building Block Use
4-Nitro-Z-D-Arg-OH is used as an arginine-containing amino acid building block for the synthesis of D-arginine-containing peptides and peptide segments in research and custom peptide manufacturing workflows. The Z protection pattern supports controlled side-chain reactivity during stepwise assembly, allowing peptide coupling conditions to proceed without premature side-chain participation. The 4-nitro substitution provides an additional handle for tailoring downstream transformations and for distinguishing this residue in analytical characterization of peptide intermediates and final products.
2. Pharmaceutical Intermediate Development
4-Nitro-Z-D-Arg-OH serves as a specialized intermediate for medicinal chemistry and process development programs that require D-arginine-derived scaffolds or protected arginine side-chain motifs. Synthetic teams use this material to access defined, stereochemically controlled building blocks for further functionalization, including conversion into downstream protected fragments used in larger synthetic sequences. The presence of the nitro group can also be leveraged as a chemically informative substituent during intermediate purification and characterization, supporting robust definition of structure in multi-step development.
3. Analytical Reference Preparation
4-Nitro-Z-D-Arg-OH is frequently employed for preparing analytical reference materials used to verify identity and purity of arginine-derived peptide intermediates and related synthetic products. Laboratories use the combination of D-stereochemistry, Z protection, and the 4-nitro substituent to generate standards that provide clear, reproducible chromatographic and mass spectrometric signatures. This is particularly valuable when monitoring complex peptide synthesis batches where arginine side-chain behavior and stereochemistry can complicate interpretation without well-defined reference compounds.
4. Chemical Biology Probe Precursors
4-Nitro-Z-D-Arg-OH is used as a precursor for chemical biology workflows that require arginine-like functionality in D-configuration, such as the preparation of labeled or derivatized arginine-containing probes and reagent fragments. Researchers rely on the protected, electronically tuned side-chain to manage reactivity during probe construction and to enable subsequent functional group installation in later steps. The nitro-substituted structure helps maintain a defined intermediate identity through synthesis and characterization, supporting reproducible probe assembly for binding studies, labeling experiments, or mechanistic reagent development.
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