Glucose nitrosation

In order to define the conditions of the growing cultures, buffered medium (VL) inoculated with E, coli ATCC 11775 and supplemented with nitrate, glucose and DMA was incubated at 37 C, and pH, nitrite concentration, nitrate concentration, cell growth and nitrosamine formation were followed (Fig. 1). Within 2 hrs, >90% of the nitrate is converted to nitrite (some of the nitrite is further reduced) and over 8 hrs the pH drops from 7.3 to 6.0. This would indicate that in experiments carried out for 20 hrs or more the control medium should be adjusted to pH 6.0 to 6.5 and nitrite should be added rather than nitrate. Such a control medium (VL) was supplemented with nitrite and DMA and NDMA formation was followed (Fig. 2). It can be seen that even without the addition of cells the rate of nitrosation is 4 fold greater than... 

Bolanos JP, Cidad P, Garcia-Nogales P, Delgado-Esteban M, Fernandez E, et al. 2004. Regulation of glucose metabolism by nitrosative stress in neural celE. Mol Aspects Med 25(1-2) 61-73. 

G. Sosnovsky, C. T. Gnewuch, and E. S. Ryoo, In the search for new anticancer drugs. XXV Role of N-nitrosated Amadori compounds derived from glucose-amino acid conjugates in cancer promotion or inhibition, J. Pharm. Sci, 82 (1993) 649-656. 

Less information is available on the occurrence of C-nitroso-compounds in foods. Stable compounds are derivatives in which the nitroso groups are bound to the tertiary carbon. Such a compound is, for example, the nitrosation product 3-deoxy-D-erythro-hexosulose, which is one of the major degradation products of glucose and other sugars (Figure 12.36). 

A kinetic and mechanistic investigation of the nitrosation of alcohols agd thiols includes some work on D-mannitol, sucrose, and D-glucose. 

---