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Key Documents

I144

Sigma-Aldrich

L-chiro-Inositol 1,4,6-tris­phosphorothioate triethylammonium salt

solid

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About This Item

MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:

form

solid

color

light yellow-green

solubility

H2O: >10 mg/mL
methanol: >10 mg/mL

storage temp.

−20°C

SMILES string

CCN(CC)CC.O[C@H]1[C@H](O)[C@H](OP(O)(O)=S)[C@@H](OP(O)(O)=S)[C@@H](O)[C@@H]1OP(O)(O)=S

Biochem/physiol Actions

Selective inhibitor of myo-inositol.

Other Notes

The n value of the salt varies from 3 to 4 for each lot.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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P M Hansbro et al.
Biochemical and biophysical research communications, 200(1), 8-15 (1994-04-15)
The ability of the novel D-myo-inositol 1,4,5-trisphosphate [Ins(1,4,5)P 3] analogues, L-chiro-inositol 1,4,6-trisphosphate [L-chr Ins(1,4,6)P3] and the corresponding trisphosphorothioate compound [L-chr Ins(1,4,6)PS3] to inhibit soluble inositol (1,4,5)P3/(1,3,4,5)P4-polyphosphate 5-phosphatase, potently and selectively, has been investigated. L-chr Ins(1,4,6)P3 competitively inhibited 5-phosphate specific dephosphorylation
D Lampe et al.
Journal of medicinal chemistry, 37(7), 907-912 (1994-04-01)
Syntheses of novel phosphorothioate-based non-Ca(2+)-releasing inhibitors of myo-inositol 1,4,5-trisphosphate 5-phosphatase are described. 1L-myo-Inositol 1,4,5-trisphosphorothioate, myo-inositol 1,3,5-trisphosphorothioate, and 1L-chiro-inositol 1,4,6-trisphosphorothioate have been synthesized from 1L-2,3,6-tri-O-benzyl-1-O-(cis-prop-1-enyl)-myo-inositol, 2,4,6-tris-O-(p-methoxybenzyl)-myo-inositol orthoformate and 1L-2,3,5-tri-O-benzyl-chiro-inositol, respectively. 1L-2,3,5-Tri-O-benzyl-chiro-inositol was also used to prepare 1L-chiro-inositol 1,4,6-trisphosphate. The phosphorothioates did
S T Safrany et al.
Biochemistry, 33(35), 10763-10769 (1994-09-06)
The interactions of synthetic analogues of D-myo-inositol 1,4,5-trisphosphate [Ins(1,4,5)P3] with the Ins(1,4,5)P3 receptor in permeabilized SH-SY5Y cells and with two key metabolic enzymes, Ins(1,4,5)P(3)3-kinase from a supernatant preparation of rat brain homogenates and Ins(1,4,5)P(3)5-phosphatase from human erythrocyte ghosts, have been

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