Biomaterial Database

Synthesis of 2-C-methyl-D-erythritol 4-phosphate: the first pathway-specific intermediate in the methylerythritol phosphate route to isoprenoids. 2000

A T Koppisch, and B S Blagg, and C D Poulter

Department of Chemistry, University of Utah, Salt Lake City 84112, USA.

[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%.

UI	MeSH Term	Description	Entries
D011106	Polyisoprenyl Phosphates	Phosphoric or pyrophosphoric acid esters of polyisoprenoids.	Isoprenoid Phosphates,Terpene Phosphates,Phosphates, Isoprenoid,Phosphates, Polyisoprenyl,Phosphates, Terpene
D004896	Erythritol	A four-carbon sugar that is found in algae, fungi, and lichens. It is twice as sweet as sucrose and can be used as a coronary vasodilator.
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013403	Sugar Phosphates		Phosphates, Sugar
D015335	Molecular Probes	A group of atoms or molecules attached to other molecules or cellular structures and used in studying the properties of these molecules and structures. Radioactive DNA or RNA sequences are used in MOLECULAR GENETICS to detect the presence of a complementary sequence by NUCLEIC ACID HYBRIDIZATION.	Molecular Probe,Probe, Molecular,Probes, Molecular