adenosine thiamine triphosphate

{{chembox

| Verifiedfields = changed

| verifiedrevid = 477242483

| ImageFile = Adenosine thiamine triphosphate.png

| ImageSize = 250px

| SystematicName = (2²R,2³R,2⁴S,2⁵R)-1⁶,13⁴-Diamino-2³,2⁴,5,7,9-pentahydroxy-13⁴,15²-dimethyl-5,7,9-trioxo-4,6,8,10-tetraoxa-5λ⁵,7λ⁵,9λ⁵-triphospha-13³λ⁵-1(9)-purina-15(5)-pyrimidina-13(5,3)-[1,3]thiazola-2(2,5)-oxolanapentadecaphan-13³-ylium

| OtherNames = P¹,P³-(Adenosine-5′-thiamine) triphosphate

| Section1 = {{Chembox Identifiers

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

| ChemSpiderID = 13082023

| InChI = 1/C22H30N9O13P3S/c1-11-15(48-10-30(11)6-13-5-25-12(2)29-19(13)23)3-4-40-45(34,35)43-47(38,39)44-46(36,37)41-7-14-17(32)18(33)22(42-14)31-9-28-16-20(24)26-8-27-21(16)31/h5,8-10,14,17-18,22,32-33H,3-4,6-7H2,1-2H3,(H6-,23,24,25,26,27,29,34,35,36,37,38,39)/p+1/t14-,17-,18-,22-/m1/s1

| SMILES1 = O=P(O)(OC[C@H]3O[C@@H](n1c2ncnc(N)c2nc1)[C@H](O)[C@@H]3O)OP(=O)(O)OP(=O)(O)OCCc4sc[n+](c4C)Cc5c(nc(nc5)C)N

| InChIKey = FGOYXNBJKMNPDH-YLNAWJOLBZ

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C22H30N9O13P3S/c1-11-15(48-10-30(11)6-13-5-25-12(2)29-19(13)23)3-4-40-45(34,35)43-47(38,39)44-46(36,37)41-7-14-17(32)18(33)22(42-14)31-9-28-16-20(24)26-8-27-21(16)31/h5,8-10,14,17-18,22,32-33H,3-4,6-7H2,1-2H3,(H6-,23,24,25,26,27,29,34,35,36,37,38,39)/p+1/t14-,17-,18-,22-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FGOYXNBJKMNPDH-SAJUPQAESA-O

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

| CASNo = 30632-11-2

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

| UNII = 9FE2NX8HJW

| CASNo_Comment = (chloride)

| PubChem = 15938962

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 71394

| SMILES = NC1=NC=NC2=C1N=CN2[C@H]3[C@H](O)[C@H](O)[C@@H](COP(OP(OP(OCCC4=C(C)[N+](CC5=CN=C(C)N=C5N)=CS4)(O)=O)(O)=O)(O)=O)O3

| MeSHName=adenosine+thiamine+triphosphate

}}

| Section2 = {{Chembox Properties

| C=22|H=31|N=9|O=13|P=3|S=1

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

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| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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Adenosine thiamine triphosphate (AThTP), or thiaminylated adenosine triphosphate, is a natural thiamine adenine nucleotide.{{cite journal |vauthors =Bettendorff L, Wirtzfeld B, Makarchikov AF |title=Discovery of a natural thiamine adenine nucleotide |journal=Nat. Chem. Biol. |volume=3 |issue=4 |pages=211–2 |year=2007 |pmid=17334376 |doi=10.1038/nchembio867|hdl=2268/518 |s2cid=28498198 |display-authors=etal|hdl-access=free }} It was discovered in Escherichia coli where it may account for up to 15 - 20% of total thiamine under carbon starvation. AThTP also exists in eukaryotic organisms such as yeast, roots of higher plants and animal tissues, albeit at a much lower concentration. It was found to exist in small amounts in the muscle, heart, brain, kidneys and liver of mice.

In E. coli AThTP is synthesized from thiamine diphosphate (ThDP) according to the following reaction catalyzed by thiamine diphosphate adenylyl transferase:{{cite journal |vauthors =Makarchikov AF, Brans A, Bettendorff L |name-list-style =amp |title=Thiamine diphosphate adenylyl transferase from E. coli: functional characterization of the enzyme synthesizing adenosine thiamine triphosphate |journal=BMC Biochem. |volume=8 |year=2007 |pmid=17705845 |doi=10.1186/1471-2091-8-17 |pages=17 |pmc=1976097 |doi-access =free }}

:ThDP + ATP (ADP) ↔ AThTP + PP_i (P_i)