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EA06838

O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate

Inhibitor of O-GlcNAcase and β-hexosaminidase

Technical Data

CAS No: 132489-69-1
Synonyms: PugNAc; (Z)-PugNAc
Product Code: EA06838
MDL No: MFCD00145022
Chemical Formula: C15H19N3O7
Molecular Weight: 353.33

References


  • Haltiwanger RS et al (1998). Modulation of O-linked N-acetylglucosamine levels on nuclear and cytoplasmic proteins in vivo using the peptide O-GlcNAc-beta-N-acetylglucosaminidase inhibitor O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate. J Biol Chem 273(6):3611-7., Alonso et al., 2014. O-GlcNAcase: Promiscuous Hexosaminidase or Key Regulator of O-GlcNAc Signaling? J Biol Chem 289(50):34433-9.
  • Khidekel N et al (2007). Probing the dynamics of O-GlcNAc glycosylation in the brain using quantitative proteomics. Nat Chem Biol 3(6):339-48., Macauley et al., 2005. O-GlcNAcase uses substrate-assisted catalysis: kinetic analysis and development of highly selective mechanism-inspired inhibitors. J Biol Chem 280(27):25313-22.
  • Perreira M et al (2006). Inhibition of O-GlcNAcase by PUGNAc is dependent upon the oxime stereochemistry. Bioorg Med Chem 14(3):837-46., Cetinbas et al., 2006. Identification of Asp174 and Asp175 as the key catalytic residues of human O-GlcNAcase by functional analysis of site-directed mutants. Biochemistry 45(11):3835-44.
  • Whitworth GE et al (2007). Analysis of PUGNAc and NAG-thiazoline as transition state analogues for human O-GlcNAcase: mechanistic and structural insights into inhibitor selectivity and transition state poise. J Am Chem Soc 129(3):635-44., Luyun et al., 2007. The protective effects of PUGNAc on cardiac function after trauma-hemorrhage are mediated via increased protein O-GlcNAc levels. Shock 27(4):402-8.
  • Zou L et al (2007). The protective effects of PUGNAc on cardiac function after trauma-hemorrhage are mediated via increased protein O-GlcNAc levels. Shock 27(4):402-8.

Solubility

Stability

Further Information


Datasheets

Specification: View
MSDS: View
Technical Bulletin: View

O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate

CAS No:
132489-69-1
Synonyms:
PugNAc
(Z)-PugNAc
MDL No:
MFCD00145022
Chemical Formula:
Molecular Weight:
353.33
Product Structure
References:
1. Haltiwanger RS et al (1998). Modulation of O-linked N-acetylglucosamine levels on nuclear and cytoplasmic proteins in vivo using the peptide O-GlcNAc-beta-N-acetylglucosaminidase inhibitor O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate. J Biol Chem 273(6):3611-7., Alonso et al., 2014. O-GlcNAcase: Promiscuous Hexosaminidase or Key Regulator of O-GlcNAc Signaling? J Biol Chem 289(50):34433-9.
2. Khidekel N et al (2007). Probing the dynamics of O-GlcNAc glycosylation in the brain using quantitative proteomics. Nat Chem Biol 3(6):339-48., Macauley et al., 2005. O-GlcNAcase uses substrate-assisted catalysis: kinetic analysis and development of highly selective mechanism-inspired inhibitors. J Biol Chem 280(27):25313-22.
3. Perreira M et al (2006). Inhibition of O-GlcNAcase by PUGNAc is dependent upon the oxime stereochemistry. Bioorg Med Chem 14(3):837-46., Cetinbas et al., 2006. Identification of Asp174 and Asp175 as the key catalytic residues of human O-GlcNAcase by functional analysis of site-directed mutants. Biochemistry 45(11):3835-44.
4. Whitworth GE et al (2007). Analysis of PUGNAc and NAG-thiazoline as transition state analogues for human O-GlcNAcase: mechanistic and structural insights into inhibitor selectivity and transition state poise. J Am Chem Soc 129(3):635-44., Luyun et al., 2007. The protective effects of PUGNAc on cardiac function after trauma-hemorrhage are mediated via increased protein O-GlcNAc levels. Shock 27(4):402-8.
5. Zou L et al (2007). The protective effects of PUGNAc on cardiac function after trauma-hemorrhage are mediated via increased protein O-GlcNAc levels. Shock 27(4):402-8.
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