Vitamin K (menaquinone) biosynthesis in bacteria: purification and probable structure of an intermediate prior to o-succinylbenzoate.
The first aromatic intermediate in the menaquinone biosynthetic pathway is o-succinylbenzoate (OSB); it is formed from chorismate/isochorismate and 2-ketoglutarate. Cell-free extracts of menD+ E. coli strains synthesize an intermediate, "X", which is converted to OSB by extracts of menC+ cells. "X" has been purified to near homogeneity by HPLC. On treatment with acid, it yields both OSB and succinylbenzene (SB). This and other data, suggest that "X" has the structure, 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (I).
D055598:Chemical Phenomena; D002621:Chemistry; D002827:Chorismic Acid / Q000378:metabolism; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004926:Escherichia coli / Q000235:genetics / Q000378:metabolism*; D007536:Isomerism; D007656:Ketoglutaric Acids / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D009154:Mutation; D010654:Phenylbutyrates / Q000378:metabolism*; D013056:Spectrophotometry, Ultraviolet; D014812:Vitamin K / Q000096:biosynthesis*
D007656:Ketoglutaric Acids; D010654:Phenylbutyrates; D014812:Vitamin K; C013691:o-succinylbenzoic acid; D002827:Chorismic Acid