title: Synthesis of 2-C-methyl-D-erythritol 4-phosphate: the first pathway-specific intermediate in the methylerythritol phosphate route to isoprenoids.
abstract: [reaction: see text] 2-C-methyl-D-erythritol 4-phosphate (4), formed from 1-deoxy-D-xylulose 5-phosphate (3), is the first pathway-specific intermediate in the methylerythritol phosphate route for the biosynthesis of isoprenoid compounds in bacteria, algae, and plant chloroplasts. In this report, 4 was synthesized from 1,2-propanediol (7) in seven steps with an overall yield of 32% and in an enantiomeric excess of 78%.
authors.affiliation: Department of Chemistry, University of Utah, Salt Lake City 84112, USA.
authors.forename: A T
authors.initials: AT
authors.lastname: Koppisch
authors.forename: B S
authors.initials: BS
authors.lastname: Blagg
authors.forename: C D
authors.initials: CD
authors.lastname: Poulter
mesh_terms: D004896:Erythritol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015335:Molecular Probes / Q000138:chemical synthesis; D011106:Polyisoprenyl Phosphates / Q000378:metabolism; D013237:Stereoisomerism; D013403:Sugar Phosphates / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C114232:2-C-methylerythritol 4-phosphate; D015335:Molecular Probes; D011106:Polyisoprenyl Phosphates; D013403:Sugar Phosphates; D004896:Erythritol