title: Neisseria gonorrhoeae 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase does not catalyze the formation of the ribo analogue.
abstract: [figure: see text] Neisseria gonorrhoeae 3-deoxy-D-arabino-heptulosonate 7-phosphate (DAH 7-P) synthase catalyzes an aldol-type condensation between D-erythrose 4-phosphate and phosphoenolpyruvate (PEP) to form 3-deoxy-D-arabino-heptulosonate 7-phosphate and not 3-deoxy-D-riboheptulosonate 7-phosphate. Similar to the Escherichia coli enzyme, N. gonorrhoeae DAH 7-P synthase condenses D-arabinose 5-phosphate with PEP to give 3-deoxy-D-manno-octulosonate 8-phosphate. Therefore, the stereochemistry of the reaction catalyzed by N. gonorrhoeae DAH 7-P synthase at C1 of the phosphorylated monosaccharide is the same as that for the E. coli enzyme, namely, re face attack.
authors: Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1065, USA.
authors: A K
authors: AK
authors: Sundaram
authors: R W
authors: RW
authors: Woodard
mesh_terms: D010723:3-Deoxy-7-Phosphoheptulonate Synthase / Q000378:metabolism*; D002384:Catalysis; D004926:Escherichia coli / Q000201:enzymology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D009344:Neisseria gonorrhoeae / Q000201:enzymology*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013403:Sugar Phosphates / Q000138:chemical synthesis*
chemical_list: D009005:Monosaccharides; D013403:Sugar Phosphates; C013469:3-deoxy-D-arabino-heptulosonate-7-phosphate; D010723:3-Deoxy-7-Phosphoheptulonate Synthase