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Adenosine thiamine triphosphate

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Adenosine thiamine triphosphate
Names
Systematic IUPAC name (2R,2R,2S,2R)-1,13-Diamino-2,2,5,7,9-pentahydroxy-13,15-dimethyl-5,7,9-trioxo-4,6,8,10-tetraoxa-5λ,7λ,9λ-triphospha-13λ-1(9)-purina-15(5)-pyrimidina-13(5,3)-thiazola-2(2,5)-oxolanapentadecaphan-13-ylium
Other names P,P-(Adenosine-5′-thiamine) triphosphate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
MeSH adenosine+thiamine+triphosphate
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: FGOYXNBJKMNPDH-SAJUPQAESA-O
  • 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/s1Key: FGOYXNBJKMNPDH-YLNAWJOLBZ
SMILES
  • NC1=NC=NC2=C1N=CN23(O)(O)(COP(OP(OP(OCCC4=C(C)(CC5=CN=C(C)N=C5N)=CS4)(O)=O)(O)=O)(O)=O)O3
  • O=P(O)(OC3O(n1c2ncnc(N)c2nc1)(O)3O)OP(=O)(O)OP(=O)(O)OCCc4sc(c4C)Cc5c(nc(nc5)C)N
Properties
Chemical formula C22H31N9O13P3S
Molar mass 754.52 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Adenosine thiamine triphosphate (AThTP), or thiaminylated adenosine triphosphate, is a natural thiamine adenine nucleotide. 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:

ThDP + ATP (ADP) ↔ AThTP + PPi (Pi)

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.

References

  1. Bettendorff L, Wirtzfeld B, Makarchikov AF, et al. (2007). "Discovery of a natural thiamine adenine nucleotide". Nat. Chem. Biol. 3 (4): 211–2. doi:10.1038/nchembio867. hdl:2268/518. PMID 17334376. S2CID 28498198.
  2. ^ Tanaka T, Yamamoto D, Sato T, Tanaka S, Usui K, Manabe M, Aoki Y, Iwashima Y, Saito Y, Mino Y, Deguchi H (2011). "Adenosine thiamine triphosphate (AThTP) inhibits poly(ADP-ribose) polymerase-1(PARP-1) activity". J Nutr Sci Vitaminol (Tokyo). 57 (2): 192–6. doi:10.3177/jnsv.57.192. PMID 21697640.
  3. Makarchikov AF, Brans A, Bettendorff L (2007). "Thiamine diphosphate adenylyl transferase from E. coli: functional characterization of the enzyme synthesizing adenosine thiamine triphosphate". BMC Biochem. 8: 17. doi:10.1186/1471-2091-8-17. PMC 1976097. PMID 17705845.

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