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NAG-thiazoline

Names

[ CAS No. ]:
179030-22-9

[ Name ]:
NAG-thiazoline

[Synonym ]:
(3aR,5R,6S,7R,7aR)-5-(Hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
3AR,5R,6S,7R,7AR-5-HYDROXYMETHYL-2-METHYL-5,6,7,7A-TETRAHYDRO-3AH-PYRANO[3,2-D]THIAZOLE-6,7-DIOL
(5R,6S,7R)-5-(Hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
NAG-thiazoline
5H-Pyrano[3,2-d]thiazole-6,7-diol, 3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-2-methyl-, (5R,6S,7R)-
N-Acetylglucosamine Thiazoline
UNII-ML5FHL557A
2epn
NGT
1hp5
5H-Pyrano[3,2-d]thiazole-6,7-diol, 3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-2-methyl-, (3aR,5R,6S,7R,7aR)-

Biological Activity

[Description]:

NAG-thiazoline is a O-GlcNAcase inhibitor with a Ki of 180 nM. NAG-thiazoline is a potent GH20 GlcNAcase (VhGlcNAcase) inhibitor with an IC50 of 11.9 μM and a Ki of 62 µM[1].

[Related Catalog]:

Research Areas >> Infection
Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Macauley MS, et al. Increasing O-GlcNAc levels: An overview of small-molecule inhibitors of O-GlcNAcase. Biochim Biophys Acta. 2010 Feb;1800(2):107-21.  

[2]. Piyanat Meekrathok, et al. NAG-thiazoline is a potent inhibitor of the Vibrio campbellii GH20 β-N-Acetylglucosaminidase. FEBS J. 2020 Nov;287(22):4982-4995.  

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
443.0±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C8H13NO4S

[ Molecular Weight ]:
219.26

[ Flash Point ]:
221.7±28.7 °C

[ Exact Mass ]:
219.056534

[ PSA ]:
107.58000

[ LogP ]:
-0.44

[ Vapour Pressure ]:
0.0±2.4 mmHg at 25°C

[ Index of Refraction ]:
1.742

Related Compounds