Adenosine 3',5'-bisphosphate

Adenosine 3',5'-bisphosphate
Names
	IUPAC name Adenosine 3′,5′-bis(dihydrogen phosphate)
	Systematic IUPAC name (2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-2-[(phosphonooxy)methyl]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). verify (what is ?) Infobox references

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 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]

References

^ Negishi M, Pedersen LG, Petrotchenko E, et al. (2001). "Structure and function of sulfotransferases". Arch. Biochem. Biophys. 390 (2): 149–57. doi:10.1006/abbi.2001.2368. PMID 11396917.
^ 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.
^ 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.
^ Ramaswamy SG, Jakoby WB (1987). "(2')3',5'-Bisphosphate nucleotidase". J. Biol. Chem. 262 (21): 10044–7. doi:10.1016/S0021-9258(18)61072-5. PMID 3038862.

[1] Negishi M, Pedersen LG, Petrotchenko E, et al. (2001). "Structure and function of sulfotransferases". 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. doi:10.1016/S0021-9258(18)61072-5. PMID 3038862.

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[4]

See also

References