Structures of Folates

The vitamers of the folate group display a high variety of different structures.

They are derivatives of folic acid (see figure), which is also denominated pteroyl glutamic acid. The latter is a purely artificial compound and usually does not appear as metabolite. The physiologically active forms such as tetrahydrofolic acid are fourfold hydrogenated (see figure). Along with tetrahydrofolate derivatives with one-carbon substituents at N5 and/or N10  occur, of which 5-methyl-, 5-formyl-, 10-formyl, 5,10-methylene- , 5,10-methenyl-, and 5-formimino-H4folate are the most abundant ones.

This so-called pteroyl monoglutamates only play a minor role in foods in comparison with the pteroyl polyglutamates, which may contain n=2 to 7 glutamates.


Structures of important folates

Folate

R1

R2

Bridge R1-R2

Tetrahydrofolic acid

H

H

5-Methyltetrahydrofolic acid

-CH3

H

-

5-Formyltetrahydrofolic acid

-CH=O

H

-

10-Formyltetrahydrofolic acid

H

-CH=O

-

5-Formiminotetrahydrofolic acid

-CH=NH

H

-

5,10-Methylenetetrahydrofolic acid

-

-

-CH2-

5,10-Methenyltetrahydrofolic acid

-

-

-CH+=