Isoprenoid biosynthesis via the MEP pathway. Synthesis of (3,4)-3,4-dihydroxy-5-oxohexylphosphonic acid, an isosteric analogue of 1-deoxy-D-xylulose 5-phosphate, the substrate of the 1-deoxy-D-xylulose 5-phosphate reducto-isomerase.
(3,4)-3,4-Dihydroxy-5-oxohexylphosphonic acid, an isosteric analogue of 1-deoxy-D-xylulose 5-phosphate (DXP), was obtained in enantiomerically pure form from (+)-2,3--benzylidene--threitol by a seven-step sequence. This phosphonate did not affect the growth of. It did not inhibit the 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), but was converted by this enzyme into (3,4)-3,4,5-trihydroxy-3-methylpentylphosphonic acid, an isosteric analogue of 2-C-methyl-D-erythritol 4-phosphate. The enzyme was, however, less efficient with the methylene phosphonate analogue than with the natural substrate.
Meyer
Odile
O
Université Louis Pasteur, CNRS UMR 7123, Institut Le Bel, 4 rue Blaise Pascal, 67070 Strasbourg Cedex, France.
Grosdemange-Billiard
Catherine
C
Tritsch
Denis
D
Rohmer
Michel
M
D019747:Aldose-Ketose Isomerases / Q000737:chemistry / Q000378:metabolism*; D004896:Erythritol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D004926:Escherichia coli / Q000378:metabolism; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D009097:Multienzyme Complexes / Q000737:chemistry / Q000378:metabolism*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010088:Oxidoreductases / Q000737:chemistry / Q000378:metabolism*; D010428:Pentosephosphates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D011106:Polyisoprenyl Phosphates / Q000096:biosynthesis* / Q000737:chemistry; D013403:Sugar Phosphates / Q000737:chemistry / Q000378:metabolism*
C482269:(3,4)-3,4-dihydroxy-5-oxohexylphosphonic acid; C109460:1-deoxylulose 5-phosphate; C114232:2-C-methylerythritol 4-phosphate; D009097:Multienzyme Complexes; D009943:Organophosphorus Compounds; D010428:Pentosephosphates; D011106:Polyisoprenyl Phosphates; D013403:Sugar Phosphates; D010088:Oxidoreductases; C114231:1-deoxy-D-xylulose 5-phosphate reductoisomerase; D019747:Aldose-Ketose Isomerases; D004896:Erythritol