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Chemical Compound Review:

NOBA (3-nitrophenyl)methanol

Synonyms: PubChem4658, SureCN94846, NSC-5388, ACMC-1BA2N, CCRIS 7971, ...

Meyer, D. et al., Tanaka, M. et al., Jackson, S.N. et al., Dass, C. et al., Qureshi, N. et al., et al.

Tanaka, Miki, Dass, Thimmaiah, Jayashree, Houghton,

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of NSC5388

While m-nitrotoluene was consecutively oxygenated to m-nitrobenzyl alcohol, m-nitrobenzaldehyde, and m-nitrobenzoic acid by XMO, the oxidation was counteracted by an alcohol dehydrogenase(s) from the E. coli host, which reduced m-nitrobenzaldehyde to m-nitrobenzyl alcohol [1].

High impact information on NSC5388

Both the leaving group of interest (choline or m-nitrobenzyl alcohol) and ethanol can be ejected during hydrolysis due to the similarity of their pK values [2].
With just 0.7% m-nitrobenzyl alcohol, even the 24+ charge state of cytochrome c is readily observed [3].
Liquid secondary ion mass spectrometry (LSIMS) mass spectra of cis-[Ru(CN)2(bpy)2] with a strong hydrogen-bonding-induced solvatochromism were measured using 3-nitrobenzyl alcohol (NBA) (oxidizing agent) and glycerol (reducing agent), and mixtures of these solvents [4].
3-Nitrobenzyl alcohol was the best substrate for cytosolic alcohol dehydrogenase (Vmax = 1.48 nmoles/min/mg protein, V/K = 3.15 X 10(-3) nmoles/min/mg protein/microM, Km = 503 microM) [5].
Positive-ion liquid secondary ionization mass spectrometry in combination with 3-nitrobenzyl alcohol as the liquid matrix was used to investigate the mass spectral features of a set of 21 N10-substituted derivatives of 2-chlorophenoxazine [6].

Analytical, diagnostic and therapeutic context of NSC5388

The positive-ion liquid secondary ion mass spectrometry spectrum also showed a minor series of peaks at m/z 1916, 1930, 1944, 1958, and 1971, consistent with the formation of matrix adducts with 3-nitrobenzyl alcohol [7].
The aerosol was generated in a Collison nebulizer, and the particles were dried in a diffusion dryer before entering a heated region saturated with the liquid matrix 3-nitrobenzyl alcohol (NBA) and then entering a cooled condensation region [8].
We found that TCEP was suitable for partial reduction of bovine insulin deposited on the target and mixed with either sinapinic acid in MALDI or glycerol and m-nitrobenzyl alcohol in LSIMS [9].
Deuterium-labeled 3-nitrobenzyl alcohol as a matrix for fast atom bombardment mass spectrometry [10].

References

Suitability of recombinant Escherichia coli and Pseudomonas putida strains for selective biotransformation of m-nitrotoluene by xylene monooxygenase. Meyer, D., Witholt, B., Schmid, A. Appl. Environ. Microbiol. (2005) [Pubmed]
Hydrolysis of phosphotriesters: determination of transition states in parallel reactions by heavy-atom isotope effects. Anderson, M.A., Shim, H., Raushel, F.M., Cleland, W.W. J. Am. Chem. Soc. (2001) [Pubmed]
Supercharged protein and peptide ions formed by electrospray ionization. Iavarone, A.T., Jurchen, J.C., Williams, E.R. Anal. Chem. (2001) [Pubmed]
The importance of preferential solvation of the CN ligands in electron- and proton-transfers observed for cis-[Ru(CN)2(bpy)2] under ion bombardment. Tanaka, M., Miki, E. J. Am. Soc. Mass Spectrom. (2002) [Pubmed]
Kinetics of conjugation and oxidation of nitrobenzyl alcohols by rat hepatic enzymes. Rickert, D.E., deBethizy, J.D., Glover, M.R., Kedderis, G.L. Biochem. Pharmacol. (1985) [Pubmed]
Liquid secondary ionization mass spectrometry and collision-induced dissociation study of 2-chloro-N10-substituted phenoxazines. Dass, C., Thimmaiah, K.N., Jayashree, B.S., Houghton, P.J. Journal of mass spectrometry : JMS. (1997) [Pubmed]
Structure of the monophosphoryl lipid A moiety obtained from the lipopolysaccharide of Chlamydia trachomatis. Qureshi, N., Kaltashov, I., Walker, K., Doroshenko, V., Cotter, R.J., Takayama, K., Sievert, T.R., Rice, P.A., Lin, J.S., Golenbock, D.T. J. Biol. Chem. (1997) [Pubmed]
Matrix addition by condensation for matrix-assisted laser desorption/ionization of collected aerosol particles. Jackson, S.N., Murray, K.K. Anal. Chem. (2002) [Pubmed]
In situ reduction suitable for matrix-assisted laser desorption/ionization and liquid secondary ionization using tris(2-carboxyethyl)phosphine. Fischer, W.H., Rivier, J.E., Craig, A.G. Rapid Commun. Mass Spectrom. (1993) [Pubmed]
Deuterium-labeled 3-nitrobenzyl alcohol as a matrix for fast atom bombardment mass spectrometry. Reddy, A.M., Mykytyn, V.V., Schram, K.H. Biomed. Environ. Mass Spectrom. (1989) [Pubmed]

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