132489-69-1 Usage
Description
O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI], also known as PUGNAc, is a (phenylcarbamoyl)oxime analog of N-acetylglucosamine (GlcNAc) that plays a crucial role in the post-translational modification of proteins. It is a white to off-white solid and acts as a reversible inhibitor of nuclear cytoplasmic O-GlcNAcase and acetyltransferase (NCOAT), a β-N-acetylglucosaminidase that removes GlcNAc from O-glycosylated proteins. PUGNAc also inhibits other hexosaminidases and exochitinases, albeit with less potency.
Uses
1. Used in Enzyme Inhibition:
O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI] is used as an inhibitor for [O-GlcNAcase, hexosaminidase A, and hexosaminidase B] to study the effects of various compounds on O-GlcNAc levels of glycoproteins.
2. Used in Cellular Studies:
In the field of cellular biology, O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI] is used as a component of the HEPES lysis buffer for [rat brain samples] to evaluate the effects of silibinin on O-GlcNAc levels of glycoproteins in Adult Retinal Pigment Epithelial-19 (ARPE-19) cells.
3. Used in Pharmaceutical Research:
O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI] is used as a research tool in the pharmaceutical industry for [developing drugs targeting O-GlcNAcylation], a post-translational modification process that plays a significant role in various cellular functions and diseases.
4. Used in Biochemical Analysis:
In the field of biochemistry, O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI] is used as a reagent for [analyzing and understanding the role of O-GlcNAcylation in protein function and stability], which can provide insights into the development of new therapeutic strategies for various diseases.
5. Used in Diagnostic Applications:
O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI] is used in the diagnostic industry as a [marker for O-GlcNAcylation levels] to detect and monitor changes in O-GlcNAcylation, which can be indicative of certain disease states or cellular processes.
Biological Activity
O -GlcNAc- β - N -acetylglucosaminidase ( O -GlcNAcase) and β -hexosaminidase inhibitor (K i values are 46 and 36 nM respectively) that increases O -GlcNAc levels ~ 2-fold in HT29 cells. Z -linked isomer is more potent than the E isomer.
Biochem/physiol Actions
O-(2-acetamido-2deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate (PUGNAc) induces insulin resistance in 3T3-L1 adipocytes by reducing insulin-prompting phosphorylation of protein kinase B (Akt) and glycogen synthase kinase 3β (GSK3β).
References
1) Macauley et al. (2005), O-GlcNAcase uses substrate-assisted catalysis: kinetic analysis and development of highly selective mechanism-inspired inhibitors; J. Biol. Chem., 280 25313
2) Kneass and Marchase (2005), Protein O-GlcNAc modulates motility-associated signaling intermediates in neutrophils; J. Biol. Chem., 280 14579
3) Zou et al. (2007), The protective effects of PUGNAC on cardiac function after trauma-hemorrhage are mediated via increased protein O-GlcNAc levels; Shock, 27 402
4) Arias et al. (2004), Prolonged incubation in PUGNAc results in increased protein O-Linked glycosylation and insulin resistance in rat skeletal muscle; Diabetes, 53 921
Check Digit Verification of cas no
The CAS Registry Mumber 132489-69-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,2,4,8 and 9 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 132489-69:
(8*1)+(7*3)+(6*2)+(5*4)+(4*8)+(3*9)+(2*6)+(1*9)=141
141 % 10 = 1
So 132489-69-1 is a valid CAS Registry Number.
InChI:InChI=1/C15H19N3O7/c1-8(20)16-11-13(22)12(21)10(7-19)24-14(11)18-25-15(23)17-9-5-3-2-4-6-9/h2-6,10-13,19,21-22H,7H2,1H3,(H,16,20)(H,17,23)/b18-14-/t10-,11-,12-,13-/m1/s1
132489-69-1Relevant articles and documents
An improved route to PUGNAc and its Galacto -configured congener
Goddard-Borger, Ethan D.,Stubbs, Keith A.
scheme or table, p. 3931 - 3934 (2010/08/06)
Figure presented An efficient, scalable, and reliable synthesis of PUGNAc and its galacto-configured congener is reported.
A divergent synthesis of 2-acyl derivatives of PUGNAc yields selective inhibitors of O-GlcNAcase
Stubbs, Keith A.,Zhang, Nelson,Vocadlo, David J.
, p. 839 - 845 (2007/10/03)
A divergent route facilitating the rapid synthesis of a series of O-(2-acetamido-2-deoxy-d-glucopyranosylidene)amino N-phenylcarbamate (PUGNAc)-based inhibitors, bearing different N-acyl groups has been developed. All compounds of this series are inhibito
Synthesis of 2-acetamido-2-deoxy-D-gluconhydroximolactone- and chitobionhydroximolactone-derived N-phenylcarbamates, potential inhibitors of β-N-acetylglucosaminidase
Beer,Maloisel,Rast,Vasella
, p. 1918 - 1922 (2007/10/02)
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