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Merck
CN

G136

Sp-Guanosine 3′,5′-cyclic monophosphorothioate triethylammonium salt

solid

Synonym(s):

Sp-Cyclic 3′5′-hydrogen phosphorothioate guanosine triethylammonium salt, Sp-cGMPS triethylammonium salt

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About This Item

Empirical Formula (Hill Notation):
C10H12N5O6PS · C6H15N
CAS Number:
86562-10-9
Molecular Weight:
462.46
NACRES:
NA.77
PubChem Substance ID:
329799838
UNSPSC Code:
41106305
MDL number:
MFCD04113738

Key Documents

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InChI key

SBVIQYPGQBMDDI-GWHKBMFWSA-N

SMILES string

CCN(CC)CC.NC1=Nc2c(ncn2[C@@H]3O[C@@H]4CO[P@](O)(=S)O[C@H]4[C@H]3O)C(=O)N1

InChI

1S/C10H12N5O6PS.C6H15N/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(20-9)1-19-22(18,23)21-6;1-4-7(5-2)6-3/h2-3,5-6,9,16H,1H2,(H,18,23)(H3,11,13,14,17);4-6H2,1-3H3/t3-,5-,6-,9-,22+;/m1./s1

form

solid

color

white

solubility

H2O: 5 mg/mL

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

Biochem/physiol Actions

Sp-cGMPS is a metabolically resistant activator of cGMP-dependent protein kinases.

Other Notes

Sp-Diastereomer of guanosine 3′,5′-cyclic monophosphorothioate.

Disclaimer

Hygroscopic

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBS9636
081M1781V
079K1328
018K1279
036K1652

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S L Archer et al.
Proceedings of the National Academy of Sciences of the United States of America, 91(16), 7583-7587 (1994-08-02)
Nitric oxide (NO)-induced relaxation is associated with increased levels of cGMP in vascular smooth muscle cells. However, the mechanism by which cGMP causes relaxation is unknown. This study tested the hypothesis that activation of Ca-sensitive K (KCa) channels, mediated by
E Butt et al.
FEBS letters, 263(1), 47-50 (1990-04-09)
The activation of the cGMP-dependent protein kinase and cAMP-dependent protein kinase by the diastereomers of guanosine 3',5'-monophosphorothioate, (Sp)-cGMPS and (Rp)-cGMPS, and 8-chloroguanosine 3',5'-monophosphorothioate, (Sp)-8-Cl-cGMPS and (Rp)-8-Cl-cGMPS, was investigated using the peptide Kemptide as substrate. The (Sp)-diastereomers, which have an axial

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