Adenosine thiamine triphosphate (AThTP), or thiaminylated adenosine triphosphate, is a natural thiamineadeninenucleotide.[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 + PPi (Pi)
Structure and functionedit
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]
Referencesedit
^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.
^ abTanaka 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.
^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. PMC1976097. PMID 17705845.
External linksedit
"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.
January 01, 1970
adenosine, thiamine, triphosphate, athtp, thiaminylated, adenosine, triphosphate, natural, thiamine, adenine, nucleotide, discovered, escherichia, coli, where, account, total, thiamine, under, carbon, starvation, athtp, also, exists, eukaryotic, organisms, suc. 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 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 5l5 7l5 9l5 triphospha 133l5 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 imageInteractive 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 YKey FGOYXNBJKMNPDH SAJUPQAESA O YInChI 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 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 O3O 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 C 22H 31N 9O 13P 3S 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 Y N Infobox references 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 PPi Pi Structure and function editThe 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 edit 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 a b 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 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 External links edit 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 Retrieved from https en wikipedia org w index php title Adenosine thiamine triphosphate amp oldid 1189405262, wikipedia, wiki, book, books, library,
