Nα-Boc-Nω-nitro-D-arginine
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Nα-Boc-Nω-nitro-D-arginine

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Category
BOC-Amino Acids
Catalog number
BAT-002988
CAS number
50913-12-7
Molecular Formula
C11H21N5O6
Molecular Weight
319.30
Nα-Boc-Nω-nitro-D-arginine
IUPAC Name
(2R)-5-[[amino(nitramido)methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
Synonyms
Boc-D-Arg(NO2)-OH; Nalpha-Boc-Nomega-Nitro-D-Arginine; Omega-Nitro-Boc-D-Arginine; (2R)-5-[[Amino(Nitramido)Methylidene]Amino]-2-[(2-Methylpropan-2-Yl)Oxycarbonylamino]Pentanoic Acid
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.40±0.1 g/cm3(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H21N5O6/c1-11(2,3)22-10(19)14-7(8(17)18)5-4-6-13-9(12)15-16(20)21/h7H,4-6H2,1-3H3,(H,14,19)(H,17,18)(H3,12,13,15)/t7-/m1/s1
InChI Key
OZSSOVRIEPAIMP-SSDOTTSWSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCCN=C(N)N[N+](=O)[O-])C(=O)O

Nα-Boc-Nω-nitro-D-arginine is a specialized reagent used in biochemical and pharmacological research. Here are some key applications of Nα-Boc-Nω-nitro-D-arginine:

Nitric Oxide Synthase Inhibition Studies: Nα-Boc-Nω-nitro-D-arginine is widely used as a selective inhibitor of nitric oxide synthase (NOS) enzymes. By inhibiting NOS activity, researchers can study the role of nitric oxide in various physiological and pathological processes. This is critical for understanding disease mechanisms and developing treatments for conditions such as hypertension, inflammation, and neurodegenerative disorders.

Peptide Synthesis: As a protected amino acid derivative, Nα-Boc-Nω-nitro-D-arginine is employed in solid-phase peptide synthesis (SPPS) to create peptides with specific sequences. The Boc and nitro groups protect the amino and guanidine functions, respectively, allowing for selective deprotection during synthesis. This reagent is essential for producing peptides for research and therapeutic applications.

Pharmacological Research: In pharmacology, Nα-Boc-Nω-nitro-D-arginine is used to elucidate the effects of nitric oxide on signaling pathways and cellular responses. By modulating NOS activity, researchers can study the downstream effects of nitric oxide in various cell types and tissues. This helps in identifying novel therapeutic targets and understanding the pharmacodynamics of nitric oxide-related drugs.

Enzyme Mechanism Studies: Nα-Boc-Nω-nitro-D-arginine is also utilized to investigate the catalytic mechanisms of nitric oxide synthase enzymes. By providing a controlled inhibition environment, researchers can explore how NOS enzymes interact with substrates and cofactors. This knowledge is fundamental in designing specific NOS inhibitors for therapeutic applications.

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