Nα-Fmoc-Nω-nitro-L-arginine
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Nα-Fmoc-Nω-nitro-L-arginine

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Category
Fmoc-Amino Acids
Catalog number
BAT-003716
CAS number
58111-94-7
Molecular Formula
C21H23N5O6
Molecular Weight
441.40
Nα-Fmoc-Nω-nitro-L-arginine
IUPAC Name
(2S)-5-[[amino(nitramido)methylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
Synonyms
Fmoc-L-Arg(NO2)-OH; (2S)-5-[[amino(nitramido)methylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Density
1.47±0.1 g/cm3(Predicted)
Melting Point
156-158 °C (dec.)
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-/m0/s1
InChI Key
RXMHIKWOZKQXCJ-SFHVURJKSA-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-L-arginine, a chemical compound prevalent in peptide synthesis and biochemical investigations, boasts a diverse range of applications. Here are the key applications highlighted with high perplexity and burstiness:

Peptide Synthesis: Embedded in solid-phase peptide synthesis, Nα-Fmoc-Nω-nitro-L-arginine emerges as a protective arginine derivative. Its Fmoc group shields the amino terminus, facilitating selective reactions during peptide elongation. This intricate process enables the creation of sophisticated peptides with exceptional purity and precision.

Nitric Oxide Research: Acting as a vital precursor, Nα-Fmoc-Nω-nitro-L-arginine plays a crucial role in the exploration of nitric oxide synthase inhibitors. Scientists utilize this compound to probe the influence of nitric oxide on diverse biological pathways, shedding light on diseases like hypertension and cardiovascular disorders. It unravels the intricacies of nitric oxide production regulation and unveils potential avenues for therapeutic interventions.

Biochemical Assays: Spanning various biochemical assays, Nα-Fmoc-Nω-nitro-L-arginine contributes significantly to the study of enzyme kinetics and substrate specificity. When incorporated into assay systems, this compound enables the assessment of protease and other enzyme activities interacting with arginine residues. This aids in identifying enzyme inhibitors and deciphering the underlying mechanisms governing enzymatic functions.

Drug Development: In the realm of pharmaceutical innovation, Nα-Fmoc-Nω-nitro-L-arginine assumes a pivotal role in designing and synthesizing arginine-based peptide medications. Through selective reduction or modification of its nitro group, researchers craft therapeutic peptides with enhanced pharmacokinetic attributes. This process streamlines the creation of novel drugs targeting specific proteins or signaling pathways, ushering in new possibilities for improved treatment modalities.

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