Phosphorylation of glycerol

By phosphorylation of glycerol deriving from fat degradation (enzyme glycerol kinase 2.7.130). 

Glycerol kinase (GK E.C. 2.7.1.30) catalyzes the enantiospecific phosphorylation of glycerol to form sn-glycerol-3-phosphate, an important intermediate for the synthesis of phospholipids. The enzyme is inexpensive and stable when immobilized. Studies with enzymes from a variety of microbial sources have shown... 

These schemes have now been used to prepare organic materials on scales of several moles. An example relevant to asymmetric synthesis is the glycerol kinase-catalyzed phosphorylation of glycerol (equation i) (6). 

Glycerol kinase is an important enzyme in glycerol metabolism. Glycerol is produced by breakdown of a fat. One pathway for metabolism of free glycerol depends on the phosphorylation of glycerol provided by glycerol kinase. 

Natural glycerophosphoric acid obt. from biol. sources is a mixt. of ca. 25% Glycerol l-monophosphate, G-550 and 75% Glycerol 2-monophosphate, G-551, [a]o ca. -0.5°. Synthetic glycerophosphoric acid prepd. by phosphorylation of glycerol has varying isomeric composition. 

Bublitz, C., and E. P. Kennedy Synthesis of phosphatides in isolated mitochondria. III. The enzymatic phosphorylation of glycerol. J. biol. Chem. 211, 951—61 (1954). 

You might note that C2 of glycerol is a prochiral center with two identical arms, a situation similar to that of citrate in the citric acid cycle (Section 22.4). As is typical for enzyme-catalyzed reactions, the phosphorylation of glycerol is selective. Only the pro-R arm undergoes reaction, although this can t be predicted in advance. 

---