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SML0244

Thiamet G

Name: Thiamet G
Brand: SIGMA

≥98% (HPLC), O-GlcNAcase inhibitor, powder

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

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₆N₂O₄S

CAS Number:

1009816-48-1

Molecular Weight:

248.30

UNSPSC Code:

12352200

PubChem Substance ID:

329825254

NACRES:

NA.77

MDL number:

MFCD15144964

Assay:

≥98% (HPLC)

Form:

powder

Storage condition:

desiccated

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Properties

Product Name

Thiamet G, ≥98% (HPLC)

Quality Segment

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

Description

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

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.

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pictograms

GHS07

signalword

Warning

hcodes

H317

pcodes

P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364

Hazard Classifications

Skin Sens. 1B

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000549767

0000549769