5,10-Methenyltetrahydrofolate

Chemical compound

5,10-Methenyltetrahydrofolate is a folate derivative and an important intermediate in the one-carbon metabolism pathway. It plays a crucial role in the biosynthesis of nucleotides and the remethylation of homocysteine to methionine.

Structure and Properties

5,10-Methenyltetrahydrofolate is a cationic form of tetrahydrofolate that contains a methenyl bridge between the N5 and N10 positions. This structure is essential for its function in transferring one-carbon units in various metabolic reactions.

Biological Role

In the one-carbon metabolism pathway, 5,10-Methenyltetrahydrofolate is involved in the conversion of 5,10-methylenetetrahydrofolate to 5-formyltetrahydrofolate and 5-methyltetrahydrofolate. It is also a substrate for the enzyme methenyltetrahydrofolate cyclohydrolase, which catalyzes its conversion to 10-formyltetrahydrofolate.

Metabolic Pathways

5,10-Methenyltetrahydrofolate is a key intermediate in the folate cycle, which is interconnected with the methionine cycle and the purine and pyrimidine synthesis pathways. It is essential for the synthesis of thymidylate and purine nucleotides, which are necessary for DNA replication and cell division.

Clinical Significance

Deficiencies in folate metabolism, including disruptions in the production or utilization of 5,10-Methenyltetrahydrofolate, can lead to megaloblastic anemia, neural tube defects, and increased levels of homocysteine, which is a risk factor for cardiovascular disease.

Related pages

• Folate
• Tetrahydrofolate
• One-carbon metabolism
• Methenyltetrahydrofolate cyclohydrolase

Gallery

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  3D space-filling model of 5,10-Methenyltetrahydrofolate

5,10-Methenyltetrahydrofolate

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  3D spacefill model of 5,10-Methenyltetrahydrofolate cation