Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Tetrahydrofolic acid: Difference between pages

{{distinguish|Tetrahydrofuran}}

{{Chembox

| Verifiedfields = changed

| verifiedrevid = 470604221

| ImageSize = 260px

| ImageAlt = Skeletal formula of tetrahydrofolic acid

| ImageFile1 = Tetrahydrofolic-acid-3D-spacefill.png

| ImageSize1 = 250

| ImageAlt1 = Space-filling model of the tetrahydrofolic acid molecule

| IUPACName = ''N''-[4-({[(6''Ξ'')-2-Amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-<small>L</small>-glutamic acid

| SystematicName = (2''S'')-2-[4-({[(6''Ξ'')-2-Amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzamido]pentanedioic acid

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 4675

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 135-16-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 43ZWB253H4

| PubChem = 91443

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| 3DMet = B04806

| Beilstein = 101189

| MeSHName = 5,6,7,8-tetrahydrofolic+acid

|Section2={{Chembox Properties

| Formula = {{chem2|C19H23N7O6}}

| MolarMass = 445.43 g/mol

| Appearance =

| Density =

| MeltingPtC = 250

| BoilingPt =

| pKa = 3.51

| Solubility = 0.27 g/L

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

'''Tetrahydrofolic acid''' ('''THFA'''), or '''tetrahydrofolate''', is a [[folic acid]] derivative.

==Metabolism==

===Human synthesis===

Tetrahydrofolic acid is produced from [[dihydrofolic acid]] by [[dihydrofolate reductase]]. This reaction is inhibited by [[methotrexate]].<ref>{{Cite journal|last1=Rajagopalan|first1=P. T. Ravi|last2=Zhang|first2=Zhiquan|last3=McCourt|first3=Lynn|last4=Dwyer|first4=Mary|last5=Benkovic|first5=Stephen J.|last6=Hammes|first6=Gordon G.|date=2002-10-15|title=Interaction of dihydrofolate reductase with methotrexate: Ensemble and single-molecule kinetics|journal=Proceedings of the National Academy of Sciences|language=en|volume=99|issue=21|pages=13481–13486|doi=10.1073/pnas.172501499|issn=0027-8424|pmc=129699|pmid=12359872|bibcode=2002PNAS...9913481R|doi-access=free}}</ref>

It is converted into [[5,10-methylenetetrahydrofolate]] by [[serine hydroxymethyltransferase]].

===Bacterial synthesis===

Many bacteria use [[dihydropteroate synthetase]] to produce [[dihydropteroate]], a molecule without function in humans. This makes it a useful target for [[Sulfonamide (medicine)|sulfonamide]] antibiotics, which compete with the [[4-Aminobenzoic acid|PABA]] precursor.

[[File:Pathway of tetrahydrofolate and antimetabolites.pdf|thumb|Pathway of tetrahydrofolate and antimetabolites]]

{{clear left}}

==Functions==

Tetrahydrofolic acid is a [[cofactor (biochemistry)|cofactor]] in many reactions, especially in the synthesis (or anabolism) of [[amino acid]]s and [[nucleic acid]]s. In addition, it serves as a carrier molecule for single-carbon moieties, that is, groups containing one carbon atom e.g. [[Methyl group|methyl]], [[Methylene group|methylene]], [[Methylidyne radical|methenyl]], [[Aldehyde|formyl]], or formimino. When combined with one such single-carbon moiety as in [[10-Formyltetrahydrofolate|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]].<ref>{{Cite web|date=2008-02-23|title=Biochemistry: The One-Carbon Pool: Folate and B12 Metabolism |url=https://liveonearth.livejournal.com/260487.html|archive-url=|archive-date=|access-date=2020-12-15|website=liveonearth.livejournal.com}}</ref><ref>{{Cite journal |last1=Yadav |first1=Manish K. |last2=Manoli |first2=Nandini M. |last3=Madhunapantula |first3=SubbaRao V. |date=2016-10-25 |editor-last=Roemer |editor-first=Klaus |title=Comparative Assessment of Vitamin-B12, Folic Acid and Homocysteine Levels in Relation to p53 Expression in Megaloblastic Anemia |journal=PLOS ONE |language=en |volume=11 |issue=10 |pages=e0164559 |doi=10.1371/journal.pone.0164559 |issn=1932-6203 |pmc=5079580 |pmid=27780269|bibcode=2016PLoSO..1164559Y |doi-access=free }}</ref><ref>{{Cite journal |last1=Aslinia |first1=F. |last2=Mazza |first2=J. J. |last3=Yale |first3=S. H. |date=2006-09-01 |title=Megaloblastic Anemia and Other Causes of Macrocytosis |journal=Clinical Medicine & Research |language=en |volume=4 |issue=3 |pages=236–241 |doi=10.3121/cmr.4.3.236 |issn=1539-4182 |pmc=1570488 |pmid=16988104}}</ref>

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.<ref>{{cite journal |vauthors=Dawson W, Maudsley DV, West GB |title=Histamine formation in guinea-pigs |journal=J. Physiol. |volume=181 |issue=4 |pages=801–9 |date=December 1965 |pmid=5881255 |pmc=1357684 |doi=10.1113/jphysiol.1965.sp007798 }}</ref>

<gallery>

Image:Dihydrofolic acid.svg|[[Dihydrofolic acid]]

Image:5,10-methylenetetrahydrofolic acid.svg|[[5,10-Methylenetetrahydrofolate|5,10-Methylenetetrahydrofolic acid]]

Image:10-formyl-tetrahydrofolic acid.svg|[[10-Formyltetrahydrofolate|10-Formyltetrahydrofolic acid]]

</gallery>

== References ==

{{reflist}}

==External links==

* [http://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=THG Tetrahydrofolate bound to proteins] in the [[Protein Data Bank|PDB]]

{{Enzyme cofactors}}

{{Authority control}}

{{DEFAULTSORT:Tetrahydrofolic Acid}}

[[Category:Folates]]

[[Category:Coenzymes]]