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G136

Sigma-Aldrich

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
MDL number:
MFCD04113738
UNSPSC Code:
41106305
PubChem Substance ID:
329799838
NACRES:
NA.77

form

solid

Quality Level

200

color

white

solubility

H2O: 5 mg/mL

shipped in

dry ice

storage temp.

−20°C

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

InChI key

SBVIQYPGQBMDDI-GWHKBMFWSA-N

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.

Caution

Hygroscopic

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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