4-diphosphocytidyl-2-C-methylerythritol

4-Diphosphocytidyl-2-C-methylerythritol (CDP-ME) is an intermediate compound in the methylerythritol phosphate pathway (MEP pathway), which is a crucial biosynthetic pathway for the production of isoprenoids in bacteria, plants, and some protozoa. This pathway is an alternative to the mevalonate pathway found in animals and fungi.

Structure and Chemical Properties

4-Diphosphocytidyl-2-C-methylerythritol is a nucleotide-linked sugar derivative. It consists of a cytidine monophosphate (CMP) moiety linked to a 2-C-methylerythritol moiety via a diphosphate bridge. The chemical formula for CDP-ME is C14H25N3O14P2, and it has a molecular weight of approximately 521.31 g/mol.

Biosynthesis

The biosynthesis of 4-diphosphocytidyl-2-C-methylerythritol occurs in the MEP pathway, which is responsible for the production of isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), the building blocks of isoprenoids. The pathway begins with the condensation of pyruvate and glyceraldehyde 3-phosphate to form 1-deoxy-D-xylulose 5-phosphate (DXP). DXP is then converted to 2-C-methyl-D-erythritol 4-phosphate (MEP) by the enzyme DXP reductoisomerase.

The conversion of MEP to CDP-ME is catalyzed by the enzyme 4-diphosphocytidyl-2-C-methylerythritol synthase (IspD). This reaction involves the transfer of a cytidine monophosphate group from cytidine triphosphate (CTP) to MEP, forming CDP-ME.

Function and Importance

CDP-ME is a key intermediate in the MEP pathway, which is essential for the biosynthesis of isoprenoids. Isoprenoids are a diverse class of compounds that play vital roles in various biological processes, including photosynthesis, respiration, and the regulation of growth hormones in plants. In bacteria, isoprenoids are important for the synthesis of cell wall components and electron transport chain carriers.

The MEP pathway is a target for the development of new antibiotics and antimalarial drugs, as it is present in many pathogenic bacteria and the malaria parasite Plasmodium falciparum, but absent in humans. Inhibitors of enzymes in the MEP pathway, such as fosmidomycin, have shown potential as therapeutic agents.

Also see

• Methylerythritol phosphate pathway
• Isoprenoid
• Mevalonate pathway
• 4-diphosphocytidyl-2-C-methylerythritol synthase
• 1-deoxy-D-xylulose 5-phosphate