Synthesis of 2-C-Methyl-d-erythritol 4-Phosphate: The First Pathway-Specific Intermediate in the Methylerythritol Phosphate Route to Isoprenoids
- 28 December 1999
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (2) , 215-217
- https://doi.org/10.1021/ol991299x
Abstract
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%.Keywords
This publication has 10 references indexed in Scilit:
- Isopentenyl diphosphate biosynthesis via a mevalonate-independent pathway: Isopentenyl monophosphate kinase catalyzes the terminal enzymatic stepProceedings of the National Academy of Sciences, 1999
- Cytidine 5′-triphosphate-dependent biosynthesis of isoprenoids: YgbP protein of Escherichia coli catalyzes the formation of 4-diphosphocytidyl-2 -C -methylerythritolProceedings of the National Academy of Sciences, 1999
- Inhibitors of the Nonmevalonate Pathway of Isoprenoid Biosynthesis as Antimalarial DrugsScience, 1999
- Biosynthesis of Mevalonic Acid from Acetyl-CoAPublished by Elsevier ,1999
- Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate‐independent pathwayFEBS Letters, 1997
- Studies on the biosynthesis of taxol: the taxane carbon skeleton is not of mevalonoid origin.Proceedings of the National Academy of Sciences, 1996
- Biosynthesis of isoprenoids (carotenoids, sterols, prenyl side-chains of chlorophylls and plastoquinone) via a novel pyruvate/glyceraldehyde 3-phosphate non-mevalonate pathway in the green alga Scenedesmus obliquusBiochemical Journal, 1996
- Prokaryotic hopanoids: the biosynthesis of the bacteriohopane skeletonEuropean Journal of Biochemistry, 1988
- Probing ergot alkaloid biosynthesis: synthesis and feeding of a proposed intermediate along the biosynthetic pathway. A new amidomalonate for tryptophan elaborationThe Journal of Organic Chemistry, 1988
- Direct synthesis of Z-unsaturated esters. A useful modification of the horner-emmons olefination.Tetrahedron Letters, 1983