2- amino-2-deoxy phosphorylation

The phosphorylation of D-glucosamine (2-amino-2-deoxy-D-glucose) was first achieved by incubating it with brain extracts and ATP.266 Crystalline, yeast hexokinase plus ATP also phosphorylates D-glucosamine, to give the 6-phosphate, at a rate at least 75 % of that of phosphorylation of D-glucose ... 

The interesting observation has been made that 3 -amino-3 -deoxy-adenosine as a suspension in phosphoryl chloride-triethyl phosphate at 4° is converted into the 5 -chloro-5 -deoxy derivative in 80% yield, but that predissolution of the nucleoside in triethyl phosphate, followed by treatment with phosphoryl chloride at 0°, yields the 5 -phosphate in 62% yield.382... 

The structural components encountered in E. coli are also present in lipid A of other bacterial sources. Thus, a survey of the structures analyzed shows that lipid A, in general, contain two g/wcoconfigured and pyranosidic D-hexosamine residues (2-amino-2-deoxy-D-glucose, GlcpN, or 2,3-diamino-2,3-dideoxy-D-glucose, GlcpN3N, also termed DAG (49,50)], which are present as a ) -(l — 6)-linked disaccharide (monosaccharide backbones have also been identified, but the respective lipid A lack endotoxic activity). The disaccharide is phosphorylated by one or, in most cases, two phosphate... 

In summary, these data show that Salmonella lipid A contains a 2-amino-6-0-(2-amino-2-deoxy-B-D-glucopyranosyl)-2-deoxy-D-glu-cose unit which carries phosphoryl residues in position 1 and 4, the glycosyl phosphate being a-linked (37). This structure is called the lipid A backbone. 

Bhat, U.R., Forsberg, L.S., Carlson, R.W. The structure of the lipid A component of Rhizobium leguminosarum bv. phaseoli lipopolysaccharide. A unique non-phosphorylated lipid A containing 2-amino-2-deoxy-gluconate, galacturonate, and glucosamine. J Biol Chem 269 (1994) 14402-14410. 

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