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Merck
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주요 문서

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SML0244

Sigma-Aldrich

Thiamet G

≥98% (HPLC)

동의어(들):

(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

실험식(Hill 표기법):
C9H16N2O4S
CAS Number:
1009816-48-1
Molecular Weight:
248.30
MDL number:
MFCD15144964
UNSPSC 코드:
12352200
PubChem Substance ID:
329825254
NACRES:
NA.77
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Quality Level

100

분석

≥98% (HPLC)

양식

powder

광학 활성

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

저장 조건

desiccated

색상

white to beige

solubility

H2O: ≥5 mg/mL at warmed to 60 °C

저장 온도

−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

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애플리케이션

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[1]
  • to treat lytically-replicating producer[2]
  • to incubate mice (C57BL/6) aortic segments to increase global O-GlcNAc levels[3]

생화학적/생리학적 작용

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.

픽토그램

Exclamation mark
GHS07

신호어

Warning

유해 및 위험 성명서

H317

Hazard Classifications

Skin Sens. 1B

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

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시험 성적서(COA)

Lot/Batch Number
0000248320
0000385807
0000385808
0000248321
0000248321

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문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

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)
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)
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
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
OGA heterozygosity suppresses intestinal tumorigenesis in Apc min/+ mice
Yang YR, et al.
Oncogenesis, 3(7), e109-e109 (2014)
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