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Thiamet G

SIGMA/SML0244 - ≥98% (HPLC)

Synonym: (3aR,5R,6S,7R,7aR)-2-(ethylamino)-3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-5H-Pyrano[3,2-d]thiazole-6,7-diol

CAS Number: 1009816-48-1
Empirical Formula (Hill Notation): C9H16N2O4S
Molecular Weight: 248.30
MDL Number: MFCD15144964
Linear Formula: C9H16N2O4S
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-SML0244-5MG 5 mg
 $141.00
1/EA		 Add To Favorites
45-SML0244-25MG 25 mg
 $557.00
1/EA		 Add To Favorites

 

assay ≥98% (HPLC)
color white to beige
form powder
InChI 1S/C9H16N2O4S/c1-2-10-9-11-5-7(14)6(13)4(3-12)15-8(5)16-9/h4-8,12-14H,2-3H2,1H3,(H,10,11)/t4-,5-,6-,7-,8-/m1/s1
InChI key PPAIMZHKIXDJRN-FMDGEEDCSA-N
optical activity [α]/D -21 to -26°, c = 0.3 in methanol
Quality Level 100 
SMILES string CCNC1=N[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]2S1
solubility H2O: ≥5 mg/mL at warmed to 60 °C
storage condition desiccated
storage temp. −20°C
Application: Thiamet G has been used as an O-GlcNAcase inhibitor:
• to treat human embryonic kidney 293 cells in order to study its effect on Wnt/beta-catenin signalling
• to treat lytically-replicating producer
• to incubate mice (C57BL/6) aortic segments to increase global O-GlcNAc levels
Biochem/physiol Actions: Thiamet G is a glycosidase inhibitor
Biochem/physiol Actions: Thiamet G is a potent inhibitor of the enzyme O-GlcNAcase (Ki = 21 nM). The compound is orally bioavailable and crosses the blood brain barrier. Thiamet G leads to an increase in O-GlcNAc-modified proteins in cell-based and in vivo assay systems, and reduces levels of phosphorylated Tau protein in rat cortex and hippocampus.
Packaging: 5, 25 mg in glass bottle
Symbol GHS07  GHS07
Signal word Warning
Hazard statements H317
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥98% (HPLC)
Storage Temp. −20°C
UNSPSC 12352200

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