From Wikipedia, the free encyclopedia
(Redirected from Tetrahydrofolate) Tetrahydrofolic acid Names IUPAC nameN-[4-({[(6Ξ)-2-Amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid
Systematic IUPAC name(2S)-2-[4-({[(6Ξ)-2-Amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzamido]pentanedioic acid
Identifiers CAS Number3D model (
JSmol)
Beilstein Reference 101189 ChEBI ChemSpiderInChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1
YKey: MSTNYGQPCMXVAQ-KIYNQFGBSA-N
YInChI=1/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1
Key: MSTNYGQPCMXVAQ-KIYNQFGBBC
O=C(O)[C@@H](NC(=O)c1ccc(cc1)NCC3N/C2=C(/N/C(=N\C2=O)N)NC3)CCC(=O)O
Except where otherwise noted, data are given for materials in their
standard state(at 25 °C [77 °F], 100 kPa).
N verify(
what is YN?)
Infobox referencesChemical compound
Tetrahydrofolic acid (THFA), or tetrahydrofolate, is a folic acid derivative.
Pathway of tetrahydrofolate and antimetabolitesIn humans, tetrahydrofolic acid is produced from dihydrofolic acid by dihydrofolate reductase. This reaction is inhibited by methotrexate.[1] It is converted into 5,10-methylenetetrahydrofolate by serine hydroxymethyltransferase.
Many bacteria produce tetrahydrofolic acid via dihydropteroate.[citation needed] Humans lack the enzymes to do this, thus molecules that shut down these enzymes are effective antibacterial compounds. For example, sulfonamide antibiotics competitively binds the active site of dihydropteroate synthetase, excluding the binding of the dihydropteroate precuror, 4-aminobenzoic acid (PABA).
Tetrahydrofolic acid is a cofactor in many reactions, especially in the synthesis (or anabolism) of amino acids and nucleic acids. In addition, it serves as a carrier molecule for single-carbon moieties, that is, groups containing one carbon atom e.g. methyl, methylene, methenyl, formyl, or formimino. When combined with one such single-carbon moiety as in 10-formyltetrahydrofolate, it acts as a donor of a group with one carbon atom. Tetrahydrofolate gets this extra carbon atom by sequestering formaldehyde produced in other processes. These single-carbon moieties are important in the formation of precursors for DNA synthesis. A shortage in tetrahydrofolic acid (FH4) can cause megaloblastic anemia.[2][3][4]
Methotrexate acts on dihydrofolate reductase, like pyrimethamine or trimethoprim, as an inhibitor and thus reduces the amount of tetrahydrofolate made. This may result in megaloblastic anemia.
Tetrahydrofolic acid is involved in the conversion of formiminoglutamic acid to glutamic acid; this may reduce the amount of histidine available for decarboxylation and protein synthesis, and hence the urinary histamine and formiminoglutamic acid may be decreased.[5]
RetroSearch is an open source project built by @garambo | Open a GitHub Issue
Search and Browse the WWW like it's 1997 | Search results from DuckDuckGo
HTML:
3.2
| Encoding:
UTF-8
| Version:
0.7.4