Ap4A

Ap4A
Names
	IUPAC name [[(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate
	Other names Diadenosine tetraphosphate; 5',5'''-Diadenosine tetraphosphate; AppppA
Identifiers
CAS Number	5542-28-9;
3D model (JSmol)	Interactive image;
PubChem CID	21706;
	SMILES C1=NC2=C(C(=N1)N)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)N5C=NC6=C5N=CN=C6N)O)O)O)O;
Properties
Chemical formula	C20H28N10O19P4
Molar mass	836.390 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Diadenosine tetraphosphate or Ap4A is a putative alarmone, ubiquitous in nature being common to everything from bacteria to humans. Adenosine polyphosphates are capable of inducing multiple physiological effects.[1] The molecule's role as a second messenger has recently been discovered in The LysRS-Ap4A-MITF signaling pathway.[2]

Myxococcus xanthus is a type of Gram-negative bacteria, and M. xanthus lysyl-tRNA synthetase (LysS) is an enzyme from the bacteria that synthesizes diadenosine tetraphosphates (Ap4A) when adenosine triphosphate (ATP) is present. Diadenosine pentaphosphate (Ap5A) is synthesized from Ap4A with ATP.[3]

References

Luo, Jiankai; Jankowski, Vera; GüNgär, Nihayrt; Neumann, Joachim; Schmitz, Wilhelm; Zidek, Walter; SchlüTer, Hartmut; Jankowski, Joachim (2004). "Endogenous diadenosine tetraphosphate, diadenosine pentaphosphate, and diadenosine hexaphosphate in human myocardial tissue". Hypertension. 43 (5): 1055–9. doi:10.1161/01.hyp.0000126110.46402.dd. PMID 15066958.
- Lee, Yu-Nee; Nechushtan, Hovav; Figov, Navah; Razin, Ehud (April 2004). "The function of lysyl-tRNA synthetase and Ap4A as signaling regulators of MITF activity in FcepsilonRI-activated mast cells". Immunity. 20 (2): 145–51. doi:10.1016/S1074-7613(04)00020-2. PMID 14975237.
Kimura, Yoshio; Tanaka, Chihiro; Oka, Manami (July 2018). "Identification of Major Enzymes Involved in the Synthesis of Diadenosine Tetraphosphate and/or Adenosine Tetraphosphate in Myxococcus xanthus". Current Microbiology. 75 (7): 811–817. doi:10.1007/s00284-018-1452-x. ISSN 1432-0991. PMID 29468302.

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[1] Luo, Jiankai; Jankowski, Vera; GüNgär, Nihayrt; Neumann, Joachim; Schmitz, Wilhelm; Zidek, Walter; SchlüTer, Hartmut; Jankowski, Joachim (2004). "Endogenous diadenosine tetraphosphate, diadenosine pentaphosphate, and diadenosine hexaphosphate in human myocardial tissue". Hypertension. 43 (5): 1055–9. doi:10.1161/01.hyp.0000126110.46402.dd. PMID 15066958.

[2] Lee, Yu-Nee; Nechushtan, Hovav; Figov, Navah; Razin, Ehud (April 2004). "The function of lysyl-tRNA synthetase and Ap4A as signaling regulators of MITF activity in FcepsilonRI-activated mast cells". Immunity. 20 (2): 145–51. doi:10.1016/S1074-7613(04)00020-2. PMID 14975237.

[3] Lee, Yu-Nee; Nechushtan, Hovav; Figov, Navah; Razin, Ehud (April 2004). "The function of lysyl-tRNA synthetase and Ap4A as signaling regulators of MITF activity in FcepsilonRI-activated mast cells". Immunity. 20 (2): 145–51. doi:10.1016/S1074-7613(04)00020-2. PMID 14975237.

[3] Kimura, Yoshio; Tanaka, Chihiro; Oka, Manami (July 2018). "Identification of Major Enzymes Involved in the Synthesis of Diadenosine Tetraphosphate and/or Adenosine Tetraphosphate in Myxococcus xanthus". Current Microbiology. 75 (7): 811–817. doi:10.1007/s00284-018-1452-x. ISSN 1432-0991. PMID 29468302.