Cyclic di-GMP

Cyclic di-GMP
Names
	Systematic IUPAC name (2R,3R,3aS,7aR,9R,10R,10aS,14aR)-2,9-Bis(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,5,10,12-tetrahydroxyoctahydro-2H,5H,7H,12H-5λ5,12λ5-difuro[3,2-d:3′,2′-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecine-5,12-dione
	Other names Cyclic diguanylate; 3',5'-Cyclic diguanylic acid; c-di-GMP; 5GP-5GP
Identifiers
CAS Number	61093-23-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	4883312 ;
PubChem CID	6323195;
CompTox Dashboard (EPA)	DTXSID801027528 DTXSID20976591, DTXSID801027528 ;
	InChI InChI=1S/C20H24N10O14P2/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1 Key: PKFDLKSEZWEFGL-MHARETSRSA-N ; InChI=1/C20H24N10O14P2/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1 Key: PKFDLKSEZWEFGL-MHARETSRBV;
	SMILES O=C7/N=C(/N)Nc1c7ncn1[C@@H]3O[C@@H]4COP(=O)(O)O[C@H]2[C@@H](O)[C@@H](O[C@@H]2COP(=O)(O)O[C@H]4[C@H]3O)n5c6NC(=N/C(=O)c6nc5)\N;
Properties
Chemical formula	C20H24N10O14P2
Molar mass	690.09 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

Cyclic di-GMP (also called cyclic diguanylate and c-di-GMP) is a second messenger used in signal transduction in a wide variety of bacteria.^[1] Cyclic di-GMP is not known to be used by archaea, and has only been observed in eukaryotes in Dictyostelium.^[2] The biological role of cyclic di-GMP was first uncovered when it was identified as an allosteric activator of a cellulose synthase found in Gluconacetobacter xylinus in order to produce microbial cellulose.^[3]

In structure, it is a cycle containing only two guanine bases linked by ribose and phosphate.

^ Tamayo R, Pratt JT, Camilli A (2007). "Roles of cyclic diguanylate in the regulation of bacterial pathogenesis". Annual Review of Microbiology. 61: 131–148. doi:10.1146/annurev.micro.61.080706.093426. PMC 2776827. PMID 17480182.
^ Chen ZH, Schaap P (August 2012). "The prokaryote messenger c-di-GMP triggers stalk cell differentiation in Dictyostelium". Nature. 488 (7413): 680–683. Bibcode:2012Natur.488..680C. doi:10.1038/nature11313. PMC 3939355. PMID 22864416.
^ Ross P, Weinhouse H, Aloni Y, Michaeli D, Weinberger-Ohana P, Mayer R, et al. (1987). "Regulation of cellulose synthesis in Acetobacter xylinum by cyclic diguanylic acid". Nature. 325 (6101): 279–281. Bibcode:1987Natur.325..279R. doi:10.1038/325279a0. PMID 18990795. S2CID 4305512.

[Tamayo-1] Tamayo R, Pratt JT, Camilli A (2007). "Roles of cyclic diguanylate in the regulation of bacterial pathogenesis". Annual Review of Microbiology. 61: 131–148. doi:10.1146/annurev.micro.61.080706.093426. PMC 2776827. PMID 17480182.

[Chen-2] Chen ZH, Schaap P (August 2012). "The prokaryote messenger c-di-GMP triggers stalk cell differentiation in Dictyostelium". Nature. 488 (7413): 680–683. Bibcode:2012Natur.488..680C. doi:10.1038/nature11313. PMC 3939355. PMID 22864416.

[Ross_1987-3] Ross P, Weinhouse H, Aloni Y, Michaeli D, Weinberger-Ohana P, Mayer R, et al. (1987). "Regulation of cellulose synthesis in Acetobacter xylinum by cyclic diguanylic acid". Nature. 325 (6101): 279–281. Bibcode:1987Natur.325..279R. doi:10.1038/325279a0. PMID 18990795. S2CID 4305512.

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