Synthesis of 2-C-methyl-D-erythritol 4-phosphate: the first pathway-specific intermediate in the methylerythritol phosphate route to isoprenoids.
[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%.
Koppisch
A T
AT
Department of Chemistry, University of Utah, Salt Lake City 84112, USA.
Blagg
B S
BS
Poulter
C D
CD
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*
C114232:2-C-methylerythritol 4-phosphate; D015335:Molecular Probes; D011106:Polyisoprenyl Phosphates; D013403:Sugar Phosphates; D004896:Erythritol