GTPgammaS

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GTPgammaS
Names
IUPAC name
[(2S,3R,4S,5S)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydroxyphosphinothioyl hydrogen phosphate
Identifiers
3D model (
JSmol
)
  • InChI=34654
    Key: XOFLBQFBSOEHOG-UUOKFMHZBU
  • InChI=1/C10H16N5O13P3S/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(26-9)1-25-29(19,20)27-30(21,22)28-31(23,24)32/h2-3,5-6,9,16-17H,1H2,(H,19,20)(H,21,22)(H2,23,24,32)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
  • S=P(O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n1cnc2c1NC(=N/C2=O)\N)[C@H](O)[C@@H]3O
Properties
C10H16N5O13P3S
Molar mass 539.24 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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GTPgammaS (GTPγS, guanosine 5'-O-[gamma-thio]triphosphate) is a non-hydrolyzable or slowly hydrolyzable

phosphoanhydride bond that links the γ-phosphate to the remainder of the nucleotide, leaving a bound guanosine diphosphate (GDP) and releasing an inorganic phosphate. This usually occurs rapidly, and the GTP-binding protein can then only be activated by exchanging the GDP for a new GTP molecule.[1] The substitution of sulfur for one of the oxygens of the γ-phosphate of GTP creates a nucleotide that either cannot be hydrolyzed or is only slowly hydrolyzed. This prevents the GTP-binding proteins from being inactivated, and allows the cellular processes that they carry out when active to be more easily studied.[2]

The consequences of the constitutive activation of GTP-binding proteins include stimulation of

autoradiography and G-protein binding studies.[6]

References