Skip to Content
MilliporeSigma
All Photos(1)

Documents

SML0244

Sigma-Aldrich

Thiamet G

≥98% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C9H16N2O4S
CAS Number:
1009816-48-1
Molecular Weight:
248.30
MDL number:
MFCD15144964
UNSPSC Code:
12352200
PubChem Substance ID:
329825254
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -21 to -26°, c = 0.3 in methanol

storage condition

desiccated

color

white to beige

solubility

H2O: ≥5 mg/mL at warmed to 60 °C

storage temp.

−20°C

SMILES string

CCNC1=N[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]2S1

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

Looking for similar products? Visit Product Comparison Guide

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 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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1B

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Scott A Yuzwa et al.
Nature chemical biology, 8(4), 393-399 (2012-03-01)
Oligomerization of tau is a key process contributing to the progressive death of neurons in Alzheimer's disease. Tau is modified by O-linked N-acetylglucosamine (O-GlcNAc), and O-GlcNAc can influence tau phosphorylation in certain cases. We therefore speculated that increasing tau O-GlcNAc
O-GlcNAc transferase inhibits KSHV propagation and modifies replication relevant viral proteins as detected by systematic O-GlcNAcylation analysis
Jochmann R, et al.
Glycobiology, 23(10), 1114-1130 (2013)
Scott A Yuzwa et al.
Nature chemical biology, 4(8), 483-490 (2008-07-01)
Pathological hyperphosphorylation of the microtubule-associated protein tau is characteristic of Alzheimer's disease (AD) and the associated tauopathies. The reciprocal relationship between phosphorylation and O-GlcNAc modification of tau and reductions in O-GlcNAc levels on tau in AD brain offers motivation for
OGA heterozygosity suppresses intestinal tumorigenesis in Apc min/+ mice
Yang YR, et al.
Oncogenesis, 3(7), e109-e109 (2014)
O-Glycosylation with O-linked beta-N-acetylglucosamine increases vascular contraction: Possible modulatory role on Interleukin-10 signaling pathway
Miguez JSG, et al.
Life Sciences, 23(10), 1114-1130 (2018)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service