8-Bromoguanosine 3',5'-cyclic monophosphate

8-Bromoguanosine 3′,5′-cyclic monophosphate is a brominated derivative of cyclic guanosine monophosphate (cGMP).[1] It acts as an activator of cGMP-dependent protein kinases.[2]

8-Bromoguanosine 3′,5′-cyclic monophosphate
Names
IUPAC name
8-Bromoguanosine 3′,5′-(hydrogen phosphate)
Preferred IUPAC name
(4aR,6R,7R,7aS)-6-(2-Amino-8-bromo-6-oxo-1,6-dihydro-9H-purin-9-yl)-2,7-dihydroxytetrahydro-2H,4H-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
Other names
8-Bromocyclic GMP;8-Bromo-cGMP; 8-Br-cyclic GMP; 8-Br-cGMP
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C10H11BrN5O7P/c11-9-13-3-6(14-10(12)15-7(3)18)16(9)8-4(17)5-2(22-8)1-21-24(19,20)23-5/h2,4-5,8,17H,1H2,(H,19,20)(H3,12,14,15,18)/t2-,4-,5-,8-/m1/s1 checkY
    Key: YUFCOOWNNHGGOD-UMMCILCDSA-N checkY
  • InChI=1/C10H11BrN5O7P/c11-9-13-3-6(14-10(12)15-7(3)18)16(9)8-4(17)5-2(22-8)1-21-24(19,20)23-5/h2,4-5,8,17H,1H2,(H,19,20)(H3,12,14,15,18)/t2-,4-,5-,8-/m1/s1
    Key: YUFCOOWNNHGGOD-UMMCILCDBZ
  • C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C4=C(C(=O)N=C(N4)N)N=C3Br)O)OP(=O)(O1)O
  • O=C4/N=C(/N)Nc1c4nc(Br)n1[C@@H]2O[C@@H]3COP(=O)(O[C@H]3[C@H]2O)O
Properties
C10H11BrN5O7P
Molar mass 424.104 g·mol−1
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

See also

References
  1. Rapoport, RM; Draznin, MB; Murad, F (Nov 1982). "Sodium nitroprusside-induced protein phosphorylation in intact rat aorta is mimicked by 8-bromo cyclic GMP" (Free full text). Proceedings of the National Academy of Sciences of the United States of America. 79 (21): 6470–4. Bibcode:1982PNAS...79.6470R. doi:10.1073/pnas.79.21.6470. ISSN 0027-8424. PMC 347148. PMID 6292902.
  2. 8-Bromoguanosine-3′,5′-cyclic monophosphate ( 8-Br-cGMP )
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