132489-69-1 Usage
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
SELECTIVE GLYCOSIDASE INHIBITORS, METHODS OF MAKING INHIBITORS, AND USES THEREOF
-
Page/Page column 47; 52-53, (2010/11/23)
The invention comprises compounds for selectively inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions containing the compounds or prodrugs of the compounds. The invention also comprises animal models and methods of making the animal models for studying diseases and disorders related to deficiency or overexpression of O-GIcNAcase, accumulation or deficiency of O-GIcNAc, and treatment of such diseases and disorders. The invention also comprises methods of treating such diseases and disorders. The invention also comprises methods of making the compounds, and methods of making selective glycosidase inhibitors
An improved synthesis of 2-acetamido-2-deoxy-D-gluconohydroximolactone (PUGNAc), a strong inhibitor of β-N-acetylglucosaminidases
Mohan, Halasyam,Vasella, Andrea
, p. 114 - 118 (2007/10/03)
O-(2-Acetamido-3,4,6-tri-O-acetyl-D-glucopyranosylidene)amino N- phenylcarbamate (1), an established inhibitor of β-N-acetylglucosaminidases, has been prepared by an improved six-step synthesis from N-acetyl-D- glucosamine.
