Adenosine 3',5'-bisphosphate

Adenosine 3',5'-bisphosphate is a form of an adenosine nucleotide with two phosphate groups attached to different carbons in the ribose ring. This is distinct from adenosine diphosphate, where the two phosphate groups are attached in a chain to the 5' carbon atom in the ring.

Adenosine 3',5'-bisphosphate

Names
IUPAC name [(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-4-hydroxy-2-(phosphonooxymethyl)oxolan-3-yl]dihydrogen phosphate
Other names 3'-Phosphoadenylate
Identifiers
CAS Number	1053-73-2
3D model (JSmol)	Interactive image
ChemSpider	140102
IUPHAR/BPS	1718
MeSH	Adenosine+bisphosphate
PubChem CID	159296
UNII	C65F80D52U
CompTox Dashboard (EPA)	DTXSID50909413
InChI InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1 Key: WHTCPDAXWFLDIH-KQYNXXCUSA-N InChI=1/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1 Key: WHTCPDAXWFLDIH-KQYNXXCUBO
SMILES c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)OP(=O)(O)O)O)N
Properties
Chemical formula	C10H15N5O10P2
Molar mass	427.20 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Adenosine 3',5'-bisphosphate is produced as a product of sulfotransferase enzymes from the donation of a sulfate group from the coenzyme 3'-phosphoadenosine-5'-phosphosulfate.[1][2] This product is then hydrolysed by 3'(2'),5'-bisphosphate nucleotidase to give adenosine monophosphate, which can then be recycled into adenosine triphosphate.[3][4]

See also

• Adenine
• Sulfur metabolism
• Acetyl-CoA

References

1. Negishi M, Pedersen LG, Petrotchenko E, et al. (2001). "Structure and function of sulfotransferases" (PDF). Arch. Biochem. Biophys. 390 (2): 149–57. doi:10.1006/abbi.2001.2368. PMID 11396917.
2. Rath VL, Verdugo D, Hemmerich S (2004). "Sulfotransferase structural biology and inhibitor discovery". Drug Discov. Today. 9 (23): 1003–11. doi:10.1016/S1359-6446(04)03273-8. PMID 15574316.
3. Farooqui AA, Balasubramanian AS (1970). "Enzymatic dephosphorylation 3'-phosphoadenosine 5'-phoaphosulfate to adenosine 5'-phosphosulfate in sheep brain". Biochim. Biophys. Acta. 198 (1): 56–65. doi:10.1016/0005-2744(70)90032-x. PMID 4313079.
4. Ramaswamy SG, Jakoby WB (1987). "(2')3',5'-Bisphosphate nucleotidase". J. Biol. Chem. 262 (21): 10044–7. PMID 3038862.