Phosphorylated ethylene glycol

Alexandratos and Zhu used as phosphorus pendant groups a phosphonate diester (PDE), a phosphorylated ethylene glycol (PEG), and a phosphorylated pentaerythritol (PPE) in order to functionalize the polystyrene resins (Scheme 11.7). ... 

The phosphate of ethylene glycol must derive from the ribitol phosphate moiety, which consequently is phosphorylated at a primary position, assumed to be 0-5 of (pro-D)-ribitol for biosynthetic reasons. In the proposed structure for the S10A repeating-unit (14), the anomeric natures of the sugar residues were not determined. The optical rotations of S10A and the hexasaccharide, [a]D +12° and +11°, respectively, indicate that they contain both a- and /3-D-linked sugar residues. 

The mechanism of toxicity of ethylene glycol involves metabolism, but unlike previous examples, this does not involve metabolic activation to a reactive metabolite. Thus, ethylene glycol is metabolized by several oxidation steps eventually to yield oxalic acid (Fig. 7.84). The first step is catalyzed by the enzyme alcohol dehydrogenase, and herein lies the key to treatment of poisoning. The result of each of the metabolic steps is the production of NADH. The imbalance in the level of this in the body is adjusted by oxidation to NAD coupled to the production of lactate. There is thus an increase in the level of lactate, and lactic acidosis may result. Also, the intermediate metabolites of ethylene glycol have metabolic effects such as the inhibition of oxidative phosphorylation, glucose metabolism, Krebs cycle, protein synthesis, RNA synthesis, and DNA replication. 

G. A. Gainanova, E. P. Zhil tsova, L. A. Kudryavtseva, S. V. Kharlamov, Sh. K. Latypov, A. P. Timosheva, A. I. Konovalov, Mixed micelles of cetyltrimethylauunonium bromide and poly(ethylene glycol)-600-monolaurate as catalysts of polyethyleneimine phosphorylation in chloroform, Russ. Chem. Bull., 2006, 57, 1411-1418. 

Figure 3. End-functionalized polyesters a) poly(ethylene glycol)-b polyester, b) phenyl azide end-capped, and c) phosphoryl choline end-capped...

---