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SML2702

Sigma-Aldrich

ST045849

≥98% (HPLC)

Synonym(s):

2-[(4-Chlorophenyl)imino]tetrahydro-4-oxo-3-(2-tricyclo[3.3.1.13,7]dec-1-ylethyl)-2H-1,3-thiazine-6-carboxylic acid, 3-(2-Adamantanylethyl)-2-[(4-chlorophenyl)azamethylene]-4-oxo-l,3-thiazaperhyd roine-6-carboxylic acid, TT04

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About This Item

Empirical Formula (Hill Notation):
C23H27ClN2O3S
CAS Number:
442665-87-4
Molecular Weight:
446.99
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C(N/1CCC23C[C@H](C4)C[C@H](C[C@H]4C3)C2)CC(SC1=N/C5=CC=C(C=C5)Cl)C(O)=O

Biochem/physiol Actions

ST045849 (TT04) is an O-GlcNAc transferase (OGT) Inhibitor (IC50/human splice variant = 30 μM/sOGT & 53 μM/ncOGT; 6.25 μM UDP-GlcNAc, 500 μM peptide substrate KKKYPGGSTPVSSANMM). ST045849 is typically employed in the 1-100 μM range for probing O-GlcNAcylation-dependent cellular processes in cultures, although low 10-50 nM and high 1-20 mM dosing ranges have also been reported. Daily oral administration is reported to prevent embryos neural tube defects at E10.5 among diabetic pregnant mice (20 mg/kg/day p.o. from E6.5 to E9.5).

Storage Class Code

11 - Combustible Solids

WGK

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’.

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Resistance to insulin action is a key cause of diabetic complications, yet much remains unknown about the molecular mechanisms that contribute to the defect. Glucose-induced insulin resistance in peripheral tissues such as the retina is mediated in part by the
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Journal of the American Chemical Society, 127(42), 14588-14589 (2005-10-20)
O-GlcNAcylation of serine and threonine residues is a dynamic and essential post-translational modification involved in signaling pathways in eukaryotes. Studies of O-GlcNAcylation would be aided by small-molecule inhibitors of O-GlcNAc transferase (OGT), the sole enzyme know to mediate this modification
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