(1Z)-2-(乙酰基氨基)-2-脱氧-N-[[(苯基氨基)羰基]氧基]-D-葡萄糖酸肟DELTA-内酯)
产品描述
Proteins can be modified post-translationally by the addition of O-linked N-acetylglucosamine (O-GlcNAc). Nuclear cytoplasmic O-GlcNAcase and acetyltransferase (NCOAT) is a β-N-acetylglucosaminidase that removes GlcNAc from O-glycosylated proteins. PUGNAc is a (phenylcarbamoyl)oxime analog of GlcNAc that reversibly inhibits NCOAT (Ki = 40-110 nM).[1],[2] It also less potently inhibits other hexosaminidases and exochitinases.[2],[3],[4] (Z)-PUGNAc is a stereoisomer of PUGNAc that is a more potent inhibitor of NCOAT than the (E) isomer, both in vitro and in cells.[5]
Reference:
[1]. Horsch, M., Hoesch, L., Vasella, A., et al. N-Acetylglucosaminono-1,5-lactone oxime and the corresponding (phenylcarbamoyl)oxime. Novel and potent inhibitors of β-N-acetylglucosaminidase. European Journal of Biochemistry 197(3), 815-818 (1991).
[2]. Dong, D.L.Y., and Hart, G.W. Purification and characterization of an O-GlcNAc selective N-acetyl-β-D-glucosaminidase from rat spleen cytosol. The Journal of Biological Chemisty 269(30), 19321-19330 (1994).
[3]. Hodge, A., Gooday, G.W., and Alexander, I.J. Inhibition of chitinolytic activities from tree species and associated fungi. Phytochemistry 41, 77-84 (1996).
[4]. Macauley, M.S., Bubb, A.K., Martinez-Fleites, C., et al. Elevation of global O-GlcNAc levels in 3T3-L1 adipocytes by selective inhibition of O-GlcNAcase does not induce insulin resistance. The Journal of Biological Chemisty 283(50), 34687-34695 (2008).
[5]. Perreira, M., Kim, E.J., Thomas, C.J., et al. Inhibition of O-GlcNAcase by PUGNAc is dependent upon the oxime stereochemistry. Bioorganic & Medicinal Chemistry 14, 837-846 (2006).
Chemical Properties
Cas No.
132489-69-1
SDF
别名
(1Z)-2-(乙酰基氨基)-2-脱氧-N-[[(苯基氨基)羰基]氧基]-D-葡萄糖酸肟DELTA-内酯
化学名
[(Z)-[(3R,4R,5S,6R)-3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino] N-phenylcarbamate
Canonical SMILES
O=C(C)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O/C1=N\OC(NC2=CC=CC=C2)=O
分子式
C15H19N3O7
分子量
353.33
溶解度
1mg/ml in DMSO, 10mg/mL in DMF
储存条件
Store at -20°C, stored under nitrogen
General tips
For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.
Shipping Condition
Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request
溶解性数据
制备储备液
1 mg
5 mg
10 mg
1 mM
2.8302 mL
14.1511 mL
28.3022 mL
5 mM
0.566 mL
2.8302 mL
5.6604 mL
10 mM
0.283 mL
1.4151 mL
2.8302 mL
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