Biosynthesis of terpenes. Preparation of (E)-1-hydroxy-2-methyl-but-2-enyl 4-diphosphate, an intermediate of the deoxyxylulose phosphate pathway.
(E)-1-hydroxy-2-methyl-but-2-enyl 4-diphosphate (E-6) was synthesized in six reaction steps from hydroxyacetone (9) and (ethoxycarbonylmethenyl)-triphenylphosphorane (11) with an overall yield of 38%. The compound was shown to be identical with the product of IspG protein, which serves as an intermediate in the nonmevalonate terpene biosynthetic pathway.
Amslinger
Sabine
S
Lehrstuhl für Organische Chemie und Biochemie, Technische Universität München, Lichtenbergstrasse 4, D-85747 Garching, Federal Republic of Germany.
Kis
Klaus
K
Hecht
Stefan
S
Adam
Petra
P
Rohdich
Felix
F
Arigoni
Duilio
D
Bacher
Adelbert
A
Eisenreich
Wolfgang
W
D000096:Acetone / Q000031:analogs & derivatives* / Q000737:chemistry; D001426:Bacterial Proteins / Q000737:chemistry; D000458:Cyanobacteria / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D004798:Enzymes; D004926:Escherichia coli / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D045782:Hemiterpenes; D009682:Magnetic Resonance Spectroscopy; D010755:Organophosphates / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D010753:Phosphoranes; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*
C469711:(ethoxycarbonylmethenyl)triphenylphosphorane; C467061:4-hydroxy-3-methyl-2-butenyl diphosphate; D001426:Bacterial Proteins; D004798:Enzymes; D045782:Hemiterpenes; D010755:Organophosphates; D009943:Organophosphorus Compounds; D010753:Phosphoranes; D013729:Terpenes; C421242:hydroxymethylbutenyl 4-diphosphate synthase; D000096:Acetone; C004809:isopentenyl pyrophosphate; C004433:acetol