399250
NG-Hydroxy-L-arginine, Monoacetate Salt
Cell permeable. A key intermediate in the biosynthesis of nitric oxide by cNOS. NOHA can be efficiently oxidized to nitric oxide and citrulline by cytochrome P450 system.
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Synonym(s):
NG-Hydroxy-L-arginine, Monoacetate Salt, NOHA, AcOH
Empirical Formula (Hill Notation):
C6H14N4O3 · xC2H4O2
CAS Number:
Molecular Weight:
190.20 (free base basis)
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.77
Recommended Products
Quality Level
Assay
≥98% (HPLC)
form
solid
potency
150 μM Ki
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
desiccated (hygroscopic)
color
white
solubility
water: 1 mg/mL
shipped in
ambient
storage temp.
−20°C
InChI
1S/C6H14N4O3.C2H4O2/c7-4(5(11)12)2-1-3-9-6(8)10-13;1-2(3)4/h4,13H,1-3,7H2,(H,11,12)(H3,8,9,10);1H3,(H,3,4)/t4-;/m0./s1
InChI key
VYMCYRPQICLHKC-WCCKRBBISA-N
General description
Cell permeable. A key intermediate in the biosynthesis of nitric oxide by constitutive nitric oxide synthase (cNOS). NOHA can be efficiently oxidized to nitric oxide and citrulline by cytochrome P450 system. A potent inhibitor of liver and macrophage arginase (Ki = 150 µM).
Cell-permeable. A key intermediate product in the biosynthesis of nitric oxide from arginine by constitutive nitric oxide synthase (cNOS). Formed by the NADPH-dependent hydroxylation of L-arginine. NOHA can be efficiently oxidized to nitric oxide and citrulline by cytochrome P450, providing an alternative biosynthetic route for the production of nitric oxide. A potent inhibitor of liver and macrophage arginase (Ki = 150 µM).
Biochem/physiol Actions
Cell permeable: yes
Primary Target
liver and macrophage arginase
liver and macrophage arginase
Packaging
Packaged under inert gas
Warning
Toxicity: Standard Handling (A)
Reconstitution
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Other Notes
Boucher, J.L., et al. 1994. Biochem. Biophys. Res. Commun. 203, 1614.
Pufahl, R.A., and Marletta, M.A. 1993. Biochem. Biophys. Res. Commun.193, 963.
Boucher, J.L., et al. 1992. Biochem. Biophys. Res. Commun.187, 880.
Stuehr, D.J., et al. 1991. J. Biol. Chem.266, 6259.
Wallace, G.C., et al. 1991. Biochem. Biophys. Res. Commun.176, 528.
Zembowicz, A., et al. 1991. Proc. Natl. Acad. Sci. USA88, 11172.
Pufahl, R.A., and Marletta, M.A. 1993. Biochem. Biophys. Res. Commun.193, 963.
Boucher, J.L., et al. 1992. Biochem. Biophys. Res. Commun.187, 880.
Stuehr, D.J., et al. 1991. J. Biol. Chem.266, 6259.
Wallace, G.C., et al. 1991. Biochem. Biophys. Res. Commun.176, 528.
Zembowicz, A., et al. 1991. Proc. Natl. Acad. Sci. USA88, 11172.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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R A Pufahl et al.
Biochemical and biophysical research communications, 193(3), 963-970 (1993-06-30)
The involvement of the protoporphyrin IX heme iron of macrophage nitric oxide synthase (NOS) in the oxidation of NG-hydroxy-L-arginine (L-NHA) to nitric oxide (NO) and citrulline was investigated by carbon monoxide (CO) inhibition studies and binding difference spectroscopy. A CO:oxygen
G C Wallace et al.
Biochemical and biophysical research communications, 176(1), 528-534 (1991-04-15)
This study describes the effects of N omega-hydroxy-L-arginine (NOHA) on endothelium dependent and endothelium independent relaxation of bovine pulmonary artery. These results are consistent with the hypothesis that NOHA is a biosynthetic intermediate in the production of nitric oxide from
D J Stuehr et al.
The Journal of biological chemistry, 266(10), 6259-6263 (1991-04-05)
Authentic N omega-hydroxy-L-arginine was synthesized and used to determine whether it is an intermediate in nitric oxide (.NO) synthesis from L-arginine by macrophage .NO synthase. The apparent Km (6.6 microM) and Vmax (99 nmol x min-1 x mg-1) observed with
A Zembowicz et al.
Proceedings of the National Academy of Sciences of the United States of America, 88(24), 11172-11176 (1991-12-15)
The hypothesis was investigated that NG-hydroxy-L-arginine (L-HOArg) is an intermediate in the biosynthesis of nitric oxide (.NO) from L-arginine (L-Arg) by the constitutive .NO synthase (NOS) present in endothelial cells (ECs). When infused through a column of bovine aortic ECs
J L Boucher et al.
Biochemical and biophysical research communications, 187(2), 880-886 (1992-09-16)
Rat liver microsomes catalyze the oxidative denitration of N omega-hydroxy-L-arginine (NOHA) by NADPH and O2 with formation of citrulline and nitrogen oxides like NO and NO2-. Besides NO2- and citrulline, whose simultaneous formation is linear for at least 20 min
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