Adenosine 3',5'-bisphosphate

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Adenosine 3',5'-bisphosphate
Adenosin-3',5'-bisphosphat.svg
Adenosine-3',5'-bisphosphate-anion-3D-spacefill.png
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
3D model (JSmol)
ChemSpider
MeSH Adenosine+bisphosphate
PubChem CID
UNII
  • 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 X mark.svgN
    Key: WHTCPDAXWFLDIH-KQYNXXCUSA-N X mark.svgN
  • 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
  • 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
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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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]

See also

Related Research Articles

<span class="mw-page-title-main">3'-Phosphoadenosine-5'-phosphosulfate</span> Chemical compound

3′-Phosphoadenosine-5′-phosphosulfate (PAPS) is a derivative of adenosine monophosphate (AMP) that is phosphorylated at the 3′ position and has a sulfate group attached to the 5′ phosphate. It is the most common coenzyme in sulfotransferase reactions and hence part of sulfation pathways. It is endogenously synthesized by organisms via the phosphorylation of adenosine 5′-phosphosulfate (APS), an intermediary metabolite. In humans such reaction is performed by bifunctional 3′-phosphoadenosine 5′-phosphosulfate synthases using ATP as the phosphate donor.

<span class="mw-page-title-main">Sulfotransferase</span>

Sulfotransferases (SULTs) are transferase enzymes that catalyze the transfer of a sulfo group from a donor molecule to an acceptor alcohol or amine. The most common sulfo group donor is 3'-phosphoadenosine-5'-phosphosulfate (PAPS). In the case of alcohol as acceptor, the product is a sulfate (R-OSO3−), whereas an amine leads to a sulfamate (R-NH-SO3−). Both reactive groups for a sulfonation via sulfotransferases may be part of a protein, lipid, carbohydrate or steroid.

In enzymology, a phosphoadenylyl-sulfate reductase (thioredoxin) is an enzyme that catalyzes the chemical reaction

An aryl sulfotransferase is an enzyme that transfers a sulfate group from phenolic sulfate esters to a phenolic acceptor substrate.

In enzymology, a chondroitin 4-sulfotransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a chondroitin 6-sulfotransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a desulfoglucosinolate sulfotransferase is an enzyme that catalyzes the chemical reaction

Estrone sulfotransferase (EST), also known as estrogen sulfotransferase, is an enzyme that catalyzes the transformation of an unconjugated estrogen like estrone into a sulfated estrogen like estrone sulfate. It is a steroid sulfotransferase and belongs to the family of transferases, to be specific, the sulfotransferases, which transfer sulfur-containing groups. This enzyme participates in androgen and estrogen metabolism and sulfur metabolism.

In enzymology, a galactosylceramide sulfotransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a glycochenodeoxycholate sulfotransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a [heparan sulfate]-glucosamine N-sulfotransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a psychosine sulfotransferase is an enzyme that catalyzes the chemical reaction:

In enzymology, a scymnol sulfotransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a thiol sulfotransferase is an enzyme that catalyzes the chemical reaction

In enzymology, an UDP-N-acetylgalactosamine-4-sulfate sulfotransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a phosphoadenylylsulfatase (EC 3.6.2.2) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">3'(2'),5'-bisphosphate nucleotidase</span>

The enzyme 3′(2′),5′-bisphosphate nucleotidase (EC 3.1.3.7) catalyzes the reaction

<span class="mw-page-title-main">PAPSS1</span> Protein-coding gene in the species Homo sapiens

Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthetase 1 is an enzyme that in humans is encoded by the PAPSS1 gene.

<span class="mw-page-title-main">GAL3ST1</span> Protein-coding gene in the species Homo sapiens

Galactosylceramide sulfotransferase is an enzyme that in humans is encoded by the GAL3ST1 gene.

<span class="mw-page-title-main">Carbohydrate sulfotransferase</span>

Carbohydrate sulfotransferases are sulfotransferase enzymes that transfer sulfate to carbohydrate groups in glycoproteins and glycolipids. Carbohydrates are used by cells for a wide range of functions from structural purposes to extracellular communication. Carbohydrates are suitable for such a wide variety of functions due to the diversity in structure generated from monosaccharide composition, glycosidic linkage positions, chain branching, and covalent modification. Possible covalent modifications include acetylation, methylation, phosphorylation, and sulfation. Sulfation, performed by carbohydrate sulfotransferases, generates carbohydrate sulfate esters. These sulfate esters are only located extracellularly, whether through excretion into the extracellular matrix (ECM) or by presentation on the cell surface. As extracellular compounds, sulfated carbohydrates are mediators of intercellular communication, cellular adhesion, and ECM maintenance.

References

  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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