3-Deoxy-D-arabino-heptulosonic acid 7-phosphate: chemical synthesis and isolation from Escherichia coli auxotrophs

A new chemical synthesis of 3-deoxy-D-arabino-heptulosonic acid 7-phosphate is described and contrasted to isolation of the same molecule from the growth medium of several different auxotrophic strains of Escherichia coli. The higher yielding chemical synthesis begins with 2-deoxyglucose while the less time-intensive biological approach proceeds directly from glucose. Growth and accumulation aspects of whole cell biological synthesis are discussed along with various aspects of the biological purification protocol. Both approaches can be utilized to produce substantial quantities of methyl (methyl 3-deoxy-D-arabino-heptulopyranosid)onate, a key intermediate for semisynthetic 3-deoxy-D-arabino-heptulosonic acid 7-phosphate and a number of its derivatives.