Cas no 5959-90-0 (Adenosine-(5')-triphospho-(5')-adenosine)

Adenosine-(5')-triphospho-(5')-adenosine (Ap?A) is a dinucleotide consisting of two adenosine moieties linked by a triphosphate bridge. This compound plays a significant role in cellular signaling and energy metabolism, serving as a substrate for various enzymes, including nucleotide pyrophosphatases and ligases. Its structural similarity to ATP and ADP makes it valuable for studying nucleotide-dependent processes, such as DNA repair and RNA synthesis. Ap?A is also implicated in stress responses and apoptosis regulation. With high purity and stability, it is widely used in biochemical research, particularly in enzymology and molecular biology, to investigate nucleotide interactions and signaling pathways. Its specificity and reactivity make it a useful tool for mechanistic studies.
Adenosine-(5')-triphospho-(5')-adenosine structure
5959-90-0 structure
Product Name:Adenosine-(5')-triphospho-(5')-adenosine
CAS No:5959-90-0
MF:C20H27N10O16P3
MW:756.407065629959
CID:367989
PubChem ID:165381
Update Time:2025-05-27

Adenosine-(5')-triphospho-(5')-adenosine Chemical and Physical Properties

Names and Identifiers

    • adenosine 5'-triphosphate 5'-adenosine
    • Diadenosine triphosphate
    • P1-(5’-ADENOSYL) P3-(5’-ADENOSYL) TRIPHOSPHATE SODIUM SALT
    • 5'-ester with adenosine
    • Adenosine5'-(tetrahydrogen triphosphate), P''&reg
    • P1,P3- 3 Diadenosine-5' triphosphate
    • ApppA
    • Ap A
    • Adenosine-(5')-triphospho-(5')-adenosine
    • Adenosine 5'-triphosphate, 5'-ester with adenosine (7CI)
    • Adenosine 5'-(tetrahydrogen triphosphate), P''→5'-ester with adenosine
    • GTPL5454
    • BDBM50184368
    • BIS(ADENOSINE)-5'-TRIPHOSPHATE
    • P1,P3-Diadenosine-5 inverted exclamation marka triphosphate
    • 5959-90-0
    • P(1),P(3)-bis(5'-adenosyl) trihydrogen triphosphate
    • adenosine(5'')triphospho(5'')adenosine
    • P(1),P(3)-bis(5''-adenosyl) trihydrogen triphosphate
    • P(1),P(3)-bis(5''-adenosyl) triphosphate
    • CHEBI:27775
    • adenosine(5')triphospho(5')adenosine
    • {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid
    • D0S5GU
    • bis[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
    • Q27074473
    • 5'Ap3A
    • A(5')p3(5')A
    • P1,P3-Bis(5'-adenosyl) triphosphate
    • C06197
    • P(1),P(3)-bis(5'-adenosyl) trihydrogen triphosphate
    • P(1),P(3)-bis(5'-adenosyl) triphosphate
    • Ap3A
    • Adenosine 5'-(tetrahydrogen triphosphate), P''-5'-ester with adenosine
    • CHEMBL407938
    • Adenosine (5')triphospho(5')adenosine
    • DB01690
    • A(5'')p3(5'')A
    • SCHEMBL1744586
    • ApppA
    • Adenosine(3)triphosphate adenosine
    • Adenosine-(5')-triphospho-(5')-adenosine
    • P1,P3-Diadenosine-5' triphosphate
    • NS00070415
    • P(1),P(3)-bis(5'-adenosyl) triphosphate
    • Inchi： 1S/C20H27N10O16P3/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(43-19)1-41-47(35,36)45-49(39,40)46-48(37,38)42-2-8-12(32)14(34)20(44-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
    • InChI Key： QCICUPZZLIQAPA-XPWFQUROSA-N
    • SMILES： P(=O)(O)(OP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3C(N)=NC=NC2=3)O1)O)O)OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3C(N)=NC=NC2=3)O1)O)O

Computed Properties

  • Exact Mass: 756.08193580g/mol
  • Monoisotopic Mass: 756.08193580g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 9
  • Hydrogen Bond Acceptor Count: 24
  • Heavy Atom Count: 49
  • Rotatable Bond Count: 12
  • Complexity: 1240
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 8
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -7.2
  • Topological Polar Surface Area: 387?2

Adenosine-(5')-triphospho-(5')-adenosine Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
A959900-10mg
Adenosine-(5')-triphospho-(5')-adenosine
 5959-90-0
10mg
 $ 155.00 2023-04-19
TRC
A959900-50mg
Adenosine-(5')-triphospho-(5')-adenosine
 5959-90-0
50mg
 $ 620.00 2023-04-19
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Adenosine-(5')-triphospho-(5')-adenosine
 5959-90-0
100mg
 $ 1194.00 2023-04-19
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Adenosine-(5')-triphospho-(5')-adenosine
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 $ 990.00 2022-07-14

Adenosine-(5')-triphospho-(5')-adenosine Production Method

Production Method 1

Reaction Conditions
1.1R:EtN(Pr-i)2, R:PCl3, S:THF, 10 min, 0°C; 45 min, 0°C
2.1R:EtN(Pr-i)2, 10 min, 0°C; 25 min, 0°C
2.2R:EtN(Pr-i)2, S:H2O, 10 min, 0°C; 10 min, 0°C
3.1R:EtN(Pr-i)2, R:PCl3, 10 min, 0°C; 25 min, 0°C
3.2R:EtN(Pr-i)2, 10 min, 0°C; 15 min, 0°C
1.1R:EtN(Pr-i)2, R:PCl3, S:THF, 10 min, 0°C; 45 min, 0°C
2.1R:EtN(Pr-i)2, S:H2O, S:THF, 0°C
2.2R:EtN(Pr-i)2, 10 min, 0°C; 35 min, 0°C
3.1R:(polymer-bound)R:EtN(Pr-i)2, S:THF, 24 h, 4°C
4.1R:S:THF, S:DMSO, 48 h, rt
5.1R:t-BuOOH, S:Me(CH2)8Me, S:THF, 2.5 h, rt
6.1R:DBU, S:THF, 48 h, rt
Reference
Solid-Phase Synthesis of Symmetrical 5',5'-Dinucleoside Mono-, Di-, Tri-, and Tetraphosphodiesters
By Ahmadibeni, Yousef and Parang, Keykavous, Organic Letters, 2007, 9(22), 4483-4486

Production Method 2

Reaction Conditions
1.1R:2-PySSPy-2, R:Et3N, R:PPh3, S:DMF
1.2C:ZnCl2, S:DMF
Reference
New Journal of Chemistry'Bimetallic Cu2+ complexes of bis-terpyridine ligands as catalysts of the cleavage of mRNA 5'-cap models. The effect of linker length and base moiety' By Maanpaeae, Leena et al, 2009 , vol.33(9), # 4 p.1853-1858

Production Method 3

Reaction Conditions
1.1C:2591-17-5, C:9014-00-0 (firefly), S:H2O
Reference
Specific synthesis of adenosine(5')tetraphospho(5')nucleoside and adenosine(5')oligophospho(5')adenosine (n > 4) catalyzed by firefly luciferase
By Ortiz, Begona et al, European Journal of Biochemistry, 1993, 212(1), 263-70

Production Method 4

Reaction Conditions
1.1R:2-PySSPy-2, R:Et3N, R:PPh3, S:DMF
1.2C:ZnCl2, S:DMF
Reference
Bimetallic Cu2+ complexes of bis-terpyridine ligands as catalysts of the cleavage of mRNA 5'-cap models. The effect of linker length and base moiety
By Maanpaeae, Leena et al, New Journal of Chemistry, 2009, 33(9), 1853-1858

Production Method 5

Reaction Conditions
1.1R:MgCl2, R:R:ZnCl2, C:9031-26-9, S:H2O, overnight, rt, pH 7.8
Reference
The duality of LysU, a catalyst for both Ap4A and Ap3A formation
By Wright, Michael et al, FEBS Journal, 2006, 273(15), 3534-3544

Production Method 6

Reaction Conditions
1.1R:2-PySSPy-2, R:P(OPh)3, S:DMF, 30 min, -5°C
1.2R:LiClO4, S:Me2CO, 0°C
2.1R:2-PySSPy-2, C:63951-94-0
Reference
Engineering Human Fhit, a Diadenosine Triphosphate Hydrolase, into an Efficient Dinucleoside Polyphosphate Synthase
By Huang, Kaisheng and Frey, Perry A., Journal of the American Chemical Society, 2004, 126(31), 9548-9549

Production Method 7

Reaction Conditions
1.1R:MgCl2, R:R:ZnCl2, C:9031-26-9, S:H2O, overnight, rt, pH 7.8
Reference
反應(yīng)條件 :
1.1R:MgCl2, R:R:ZnCl2, C:9031-26-9, S:H2O, overnight, rt, pH 7.8
The duality of LysU, a catalyst for both Ap4A and Ap3A formation
By Wright, Michael et al, FEBS Journal, 2006, 273(15), 3534-3544

Production Method 8

Reaction Conditions
1.1C:2591-17-5, C:9014-00-0 (firefly), S:H2O
Reference
反應(yīng)條件 :
1.1C:2591-17-5, C:9014-00-0 (firefly), S:H2O
Specific synthesis of adenosine(5')tetraphospho(5')nucleoside and adenosine(5')oligophospho(5')adenosine (n > 4) catalyzed by firefly luciferase
By Ortiz, Begona et al, European Journal of Biochemistry, 1993, 212(1), 263-70

Production Method 9

Reaction Conditions
1.1R:2-PySSPy-2, R:P(OPh)3, S:DMF, 30 min, -5°C
1.2R:LiClO4, S:Me2CO, 0°C'
2.1R:2-PySSPy-2, C:63951-94-0
Reference
Journal of the American Chemical Society'Engineering Human Fhit, a Diadenosine Triphosphate Hydrolase, into an Efficient Dinucleoside Polyphosphate Synthase' By Huang, Kaisheng and Frey, Perry A., 2004 , vol.126(31), # 4 p.9548-9549

Production Method 10

Reaction Conditions
1.1R:EtN(Pr-i)2, R:PCl3, S:THF, 10 min, 0°C; 45 min, 0°C
2.1R:EtN(Pr-i)2, 10 min, 0°C; 25 min, 0°C
2.2R:EtN(Pr-i)2, S:H2O, 10 min, 0°C; 10 min, 0°C
3.1R:EtN(Pr-i)2, R:PCl3, 10 min, 0°C; 25 min, 0°C
3.2R:EtN(Pr-i)2, 10 min, 0°C; 15 min, 0°C
1.1R:EtN(Pr-i)2, R:PCl3, S:THF, 10 min, 0°C; 45 min, 0°C
2.1R:EtN(Pr-i)2, S:H2O, S:THF, 0°C
2.2R:EtN(Pr-i)2, 10 min, 0°C; 35 min, 0°C
3.1R:(polymer-bound)R:EtN(Pr-i)2, S:THF, 24 h, 4°C
4.1R:S:THF, S:DMSO, 48 h, rt
5.1R:t-BuOOH, S:Me(CH2)8Me, S:THF, 2.5 h, rt
6.1R:DBU, S:THF, 48 h, rt
Reference
Organic Letters'Solid-Phase Synthesis of Symmetrical 5',5'-Dinucleoside Mono-, Di-, Tri-, and Tetraphosphodiesters' By Ahmadibeni, Yousef and Parang, Keykavous, 2007 , vol.9(22), # 4 p.4483-4486

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(CAS:5959-90-0)Adenosine-(5')-triphospho-(5')-adenosine
Order Number:NC13242
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Quantity:10g
Purity:97%
Pricing Information Last Updated:Friday, 18 July 2025 16:04
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(CAS:5959-90-0)Adenosine-(5')-triphospho-(5')-adenosine
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Purity:97%
Quantity:10g
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