Nitromalondialdehyde

Nitromalondialdehyde reaction with arginine The products formed by nitromalondialdehyde have been characterized (Signor et al. 1971). Thus N-acetylarginine reacts with nitromalondialdehyde to yield a nitropyrimidine derivative as indicated below in eq. (3.2.). 

Since the optimum pH range for the reaction is between pH 12 and 14, the usefulness of nitromalondialdehyde is restricted to denatured proteins. 

To modify the S-carboxymethylated B chain of insulin. Signor et al. (1971) added about 3.0 mmoles of the peptide dissolved in 1.0 ml of 1 M NaOH to 1 ml of water containing 10 mg of nitromalondialdehyde (70 mmoles). After 2 hr at 0-5°C excess modification reagent was removed by gel filtration using 50% formic acid as eluent. 

Arginine residues modified by nitromalondialdehyde are resistant to tryptic digestion. However, reduction of the derivative by sodium borohydride yields tetrahydropyrimidyl compounds which are susceptible to hydrolysis by trypsin. Modification by nitromalondialdehyde thereby permits the restriction of tryptic digestion to lysine... 

Nitropyrrole can be prepared by decarboxylation of 4-nitropyrrole-2-carboxylic acid, whose ethyl ester is simply accessible in 75 % yield by condensation of the sodium derivative of nitromalondialdehyde with glycine ester.227... 

Davis, M. C. Evironmentally Mendly method for the preparation of 2,4-dinitrophenol via the cyclocondensation reaction of 2-nitromalondialdehyde and nitroacetone. US Patent 6960696, 2005 Chem. Abstr. 2005,143,440055. 

On refluxing a methanolic solution of freshly prepared [Co(H2L63)]M/2CH30H with the sodium salt of nitromalondialdehyde monohydrate, the macrocyclic complex [Co(L80)] (R = CH3, R = NO2) is formed. In its mass spectrum the peak with mjz 412 corresponding to P+- is present [86]. This product is low spin = 2.28), like the starting compound, but in contrast to the former it is stable in air. 

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