Nα-Fmoc-Nω-nitro-D-arginine
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Nα-Fmoc-Nω-nitro-D-arginine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007741
CAS number
160347-94-4
Molecular Formula
C21H23N5O6
Molecular Weight
441.40
Nα-Fmoc-Nω-nitro-D-arginine
IUPAC Name
(2R)-5-[[amino(nitramido)methylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
Synonyms
Fmoc-D-Arg(NO2)-OH; Fmoc-nw-nitro-d-arginine; D-Ornithine, N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-N5-[imino(nitroamino)methyl]-; N-alpha-(9-Fluorenylmethoxycarbonyl)-N-omega-nitro-D-arginine; (2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5-(N'-nitrocarbamimidamido)pentanoic acid; (2R)-5-[[amino(nitramido)methylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Melting Point
153-158 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C21H23N5O6/c22-20(25-26(30)31)23-11-5-10-18(19(27)28)24-21(29)32-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17-18H,5,10-12H2,(H,24,29)(H,27,28)(H3,22,23,25)/t18-/m1/s1
InChI Key
RXMHIKWOZKQXCJ-GOSISDBHSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCCN=C(N)N[N+](=O)[O-])C(=O)O

Nα-Fmoc-Nω-nitro-D-arginine is a fluorinated amino acid derivative utilized in peptide synthesis and biochemical research. Here are its key applications:

Peptide Synthesis: Integral to solid-phase peptide synthesis, Nα-Fmoc-Nω-nitro-D-arginine plays a crucial role in introducing arginine residues into peptide sequences. The Fmoc protection group ensures efficient coupling reactions, maintaining sequence fidelity essential for crafting peptides with specific functional properties tailored for diverse research and therapeutic endeavors.

Protease Inhibition Studies: Leveraging its structural resemblance to the natural substrate, Nα-Fmoc-Nω-nitro-D-arginine is a cornerstone in studies delving into protease activity and inhibition mechanisms. Researchers harness this derivative to design peptide-based inhibitors, evaluating their effectiveness in blocking protease-mediated cleavage. This research avenue contributes significantly to drug discovery initiatives targeting diseases linked to protease dysregulation, such as cancer and viral infections.

Bioconjugation: A versatile functional group, Nα-Fmoc-Nω-nitro-D-arginine is pivotal in bioconjugation methodologies, facilitating the attachment of peptides to various biomolecules or surfaces. The nitro group’s modifiability enables further chemical reactions, empowering the creation of conjugates vital for diagnostic imaging or targeted drug delivery applications. This versatile application streamlines the development of cutting-edge bioanalytical tools and therapeutic agents.

Molecular Modeling: In the realm of molecular modeling and structural biology, Nα-Fmoc-Nω-nitro-D-arginine serves as a key player in exploring interactions between peptides and their molecular targets. Computational studies leveraging this derivative aid in predicting binding affinities and unraveling the conformational dynamics of peptide-protein complexes. This in-depth analysis provides invaluable insights into protein functionality, guiding the design of novel peptide-based therapeutic strategies.

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