Adenosine thiamine triphosphate

Adenosine thiamine triphosphate

Names
Systematic IUPAC name (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
Other names P1,P3-(Adenosine-5′-thiamine) triphosphate
Identifiers
CAS Number	30632-11-2 (chloride) Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:71394 N
ChemSpider	13082023 Y
MeSH	adenosine+thiamine+triphosphate
PubChem CID	15938962
UNII	9FE2NX8HJW Y
CompTox Dashboard (EPA)	DTXSID40579927
InChI InChI=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 Y Key: FGOYXNBJKMNPDH-SAJUPQAESA-O Y 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 Key: FGOYXNBJKMNPDH-YLNAWJOLBZ
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 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
Properties
Chemical formula	C22H31N9O13P3S
Molar mass	754.52 g·mol−1
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 references

Adenosine thiamine triphosphate (AThTP), or thiaminylated adenosine triphosphate, is a natural thiamine adenine nucleotide.^[1] 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.^[2]

In E. coli AThTP is synthesized from thiamine diphosphate (ThDP) according to the following reaction catalyzed by thiamine diphosphate adenylyl transferase:^[3]

ThDP + ATP (ADP) ↔ AThTP + PP_i (P_i)

Structure and function

The molecule is made up of thiamine and adenosine joined together with phosphate groups. It is similar in structure to NAD+. The function of AThTP is not currently known but it has been shown to inhibit the activity of PARP-1.^[2]

References

External links

• "A first for vitamins". Nature. 446 (7132): 112–113. 2007. doi:10.1038/446112a.
• Jordan F (2007). "Adenosine triphosphate and thiamine cross paths". Nat. Chem. Biol. 3 (4): 202–3. doi:10.1038/nchembio0407-202. PMID 17372602.

This page was last edited on 11 December 2023, at 16:46