Adenosine thiamine triphosphate
Adenosine thiamine triphosphate
Names
Systematic IUPAC name
(22 R ,23 R ,24 S ,25 R )-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-133 λ5 -1(9)-purina-15(5)-pyrimidina-13(5,3)-[1,3]thiazola-2(2,5)-oxolanapentadecaphan-133 -ylium
Other names
P 1 ,P 3 -(Adenosine-5′-thiamine) triphosphate
Identifiers
ChEBI
ChemSpider
MeSH
adenosine+thiamine+triphosphate
UNII
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
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
C 22 H 31 N 9 O 13 P 3 S
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).
Chemical compound
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 + 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.[ 2]
References
^ 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