NAG-thiazoline
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MedKoo CAT#: 464839

CAS#: 179030-22-9

Description: NAG-thiazoline is an inhibitor of O-GlcNAcase (OGA; Ki = 180 nM).1 It is active against V. campbellii (MIC = 0.5 µM).

Chemical Structure

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NAG-thiazoline
CAS# 179030-22-9
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464839
Name: NAG-thiazoline
CAS#: 179030-22-9
Chemical Formula: C8H13NO4S
Exact Mass: 219.06
Molecular Weight: 219.255
Elemental Analysis: C, 43.82; H, 5.98; N, 6.39; O, 29.19; S, 14.62

Price and Availability

Size Price Availability Quantity
5mg USD 285 2 Weeks
10mg USD 450 2 Weeks
25mg USD 950 2 Weeks
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Related CAS #: 179030-22-9,  

Synonym: NAG-thiazoline; NAGthiazoline; NAG thiazoline; GlcNAc-thiazoline; GlcNActhiazoline; GlcNAc thiazoline;

IUPAC/Chemical Name: (3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-methyl-3a,6,7,7a-tetrahydro-5H-pyrano[3,2-d]thiazole-6,7-diol

InChi Key: DRHXTSWSUAJOJZ-FMDGEEDCSA-N

InChi Code: InChI=1S/C8H13NO4S/c1-3-9-5-7(12)6(11)4(2-10)13-8(5)14-3/h4-8,10-12H,2H2,1H3/t4-,5-,6-,7-,8-/m1/s1

SMILES Code: O[C@@H]1[C@@]2([C@]([H])(O[C@H](CO)[C@H]1O)SC(C)=N2)[H]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: NAG-thiazoline is an inhibitor of O-GlcNAcase (OGA; Ki = 180 nM).
In vitro activity: This study examined NAG-thiazoline (NGT)-mediated inhibition of a recombinantly expressed GH20 β-N-acetylglucosaminidase, namely VhGlcNAcase from Vibrio campbellii (formerly V. harveyi) ATCC BAA-1116. NGT strongly inhibited VhGlcNAcase with an IC50 of 11.9 ± 1.0 μm and Ki 62 ± 3 µm, respectively. NGT was also found to completely inhibit the growth of V. campbellii strain 650 with an minimal inhibitory concentration value of 0.5 µm. Reference: FEBS J. 2020 Nov;287(22):4982-4995. https://pubmed.ncbi.nlm.nih.gov/32145141/
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 136.83
DMSO 25.0 114.02
Ethanol 30.0 136.83
PBS (pH 7.2) 5.0 22.80

Preparing Stock Solutions

The following data is based on the product molecular weight 219.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Meekrathok P, Stubbs KA, Aunkham A, Kaewmaneewat A, Kardkuntod A, Bulmer DM, van den Berg B, Suginta W. NAG-thiazoline is a potent inhibitor of the Vibrio campbellii GH20 β-N-Acetylglucosaminidase. FEBS J. 2020 Nov;287(22):4982-4995. doi: 10.1111/febs.15283. Epub 2020 Mar 23. PMID: 32145141. 2. Reid CW, Blackburn NT, Clarke AJ. The effect of NAG-thiazoline on morphology and surface hydrophobicity of Escherichia coli. FEMS Microbiol Lett. 2004 May 15;234(2):343-8. doi: 10.1016/j.femsle.2004.03.047. PMID: 15135542.
In vitro protocol: 1. Meekrathok P, Stubbs KA, Aunkham A, Kaewmaneewat A, Kardkuntod A, Bulmer DM, van den Berg B, Suginta W. NAG-thiazoline is a potent inhibitor of the Vibrio campbellii GH20 β-N-Acetylglucosaminidase. FEBS J. 2020 Nov;287(22):4982-4995. doi: 10.1111/febs.15283. Epub 2020 Mar 23. PMID: 32145141. 2. Reid CW, Blackburn NT, Clarke AJ. The effect of NAG-thiazoline on morphology and surface hydrophobicity of Escherichia coli. FEMS Microbiol Lett. 2004 May 15;234(2):343-8. doi: 10.1016/j.femsle.2004.03.047. PMID: 15135542.
In vivo protocol: TBD

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1: Meekrathok P, Stubbs KA, Aunkham A, Kaewmaneewat A, Kardkuntod A, Bulmer DM, van den Berg B, Suginta W. NAG-thiazoline is a potent inhibitor of the Vibrio campbellii GH20 β-N-Acetylglucosaminidase. FEBS J. 2020 Nov;287(22):4982-4995. doi: 10.1111/febs.15283. Epub 2020 Mar 23. PMID: 32145141.

2: Peng P, Wang J, Ding N, Zhou M, Gu Z, Shi Y, Gong C, Zhao G, Deng Y. Alteration of O-GlcNAcylation affects assembly and axonal transport of neurofilament via phosphorylation. Neurosci Lett. 2019 Apr 17;698:97-104. doi: 10.1016/j.neulet.2018.11.001. Epub 2018 Nov 3. PMID: 30395884.

3: Krejzová J, Kulik N, Slámová K, Křen V. Expression of human β-N- acetylhexosaminidase B in yeast eases the search for selective inhibitors. Enzyme Microb Technol. 2016 Jul;89:1-6. doi: 10.1016/j.enzmictec.2016.03.003. Epub 2016 Mar 9. PMID: 27233122.

4: Alteen MG, Oehler V, Nemčovičová I, Wilson IB, Vocadlo DJ, Gloster TM. Mechanism of Human Nucleocytoplasmic Hexosaminidase D. Biochemistry. 2016 May 17;55(19):2735-47. doi: 10.1021/acs.biochem.5b01285. Epub 2016 May 5. PMID: 27149221; PMCID: PMC4878814.

5: Kong H, Chen W, Lu H, Yang Q, Dong Y, Wang D, Zhang J. Synthesis of NAG- thiazoline-derived inhibitors for β-N-acetyl-d-hexosaminidases. Carbohydr Res. 2015 Sep 2;413:135-44. doi: 10.1016/j.carres.2015.06.004. Epub 2015 Jun 16. PMID: 26142545.

6: Krejzová J, Kalachova L, Šimon P, Pelantová H, Slámová K, Křen V. Inhibition of microbial β-N-acetylhexosaminidases by 4-deoxy- and galacto-analogues of NAG- thiazoline. Bioorg Med Chem Lett. 2014 Nov 15;24(22):5321-3. doi: 10.1016/j.bmcl.2014.09.066. Epub 2014 Oct 2. PMID: 25442323.

7: Liu T, Xia M, Zhang H, Zhou H, Wang J, Shen X, Yang Q. Exploring NAG- thiazoline and its derivatives as inhibitors of chitinolytic β-acetylglucosaminidases. FEBS Lett. 2015 Jan 2;589(1):110-6. doi: 10.1016/j.febslet.2014.11.032. Epub 2014 Nov 29. PMID: 25436416.

8: Krejzová J, Simon P, Kalachova L, Kulik N, Bojarová P, Marhol P, Pelantová H, Cvačka J, Ettrich R, Slámová K, Křen V. Inhibition of GlcNAc-processing glycosidases by C-6-azido-NAG-thiazoline and its derivatives. Molecules. 2014 Mar 20;19(3):3471-88. doi: 10.3390/molecules19033471. PMID: 24658571; PMCID: PMC6271965.

9: Pluvinage B, Stubbs KA, Hattie M, Vocadlo DJ, Boraston AB. Inhibition of the family 20 glycoside hydrolase catalytic modules in the Streptococcus pneumoniae exo-β-D-N-acetylglucosaminidase, StrH. Org Biomol Chem. 2013 Dec 7;11(45):7907-15. doi: 10.1039/c3ob41579a. Epub 2013 Oct 16. PMID: 24132305.

10: de Alencar NA, Sousa PR, Silva JR, Lameira J, Alves CN, Martí S, Moliner V. Computational analysis of human OGA structure in complex with PUGNAc and NAG- thiazoline derivatives. J Chem Inf Model. 2012 Oct 22;52(10):2775-83. doi: 10.1021/ci2006005. Epub 2012 Sep 18. PMID: 22937904.

11: Li J, Li Z, Li T, Lin L, Zhang Y, Guo L, Xu Y, Zhao W, Wang P. Identification of a specific inhibitor of nOGA - a caspase-3 cleaved O-GlcNAcase variant during apoptosis. Biochemistry (Mosc). 2012 Feb;77(2):194-200. doi: 10.1134/S0006297912020113. PMID: 22348480.

12: Lameira J, Alves CN, Tuñón I, Martí S, Moliner V. Enzyme molecular mechanism as a starting point to design new inhibitors: a theoretical study of O-GlcNAcase. J Phys Chem B. 2011 May 26;115(20):6764-75. doi: 10.1021/jp202079e. Epub 2011 May 4. PMID: 21542586.

13: Laczy B, Marsh SA, Brocks CA, Wittmann I, Chatham JC. Inhibition of O-GlcNAcase in perfused rat hearts by NAG-thiazolines at the time of reperfusion is cardioprotective in an O-GlcNAc-dependent manner. Am J Physiol Heart Circ Physiol. 2010 Nov;299(5):H1715-27. doi: 10.1152/ajpheart.00337.2010. Epub 2010 Sep 10. PMID: 20833964; PMCID: PMC2993218.

14: Macauley MS, Vocadlo DJ. Increasing O-GlcNAc levels: An overview of small- molecule inhibitors of O-GlcNAcase. Biochim Biophys Acta. 2010 Feb;1800(2):107-21. doi: 10.1016/j.bbagen.2009.07.028. Epub 2009 Aug 4. PMID: 19664691.

15: Macauley MS, Vocadlo DJ. Enzymatic characterization and inhibition of the nuclear variant of human O-GlcNAcase. Carbohydr Res. 2009 Jun 12;344(9):1079-84. doi: 10.1016/j.carres.2009.04.017. Epub 2009 Apr 20. PMID: 19423084.

16: Abbott DW, Macauley MS, Vocadlo DJ, Boraston AB. Streptococcus pneumoniae endohexosaminidase D, structural and mechanistic insight into substrate-assisted catalysis in family 85 glycoside hydrolases. J Biol Chem. 2009 Apr 24;284(17):11676-89. doi: 10.1074/jbc.M809663200. Epub 2009 Jan 30. PMID: 19181667; PMCID: PMC2670171.

17: Lameira J, Alves CN, Moliner V, Martí S, Kanaan N, Tuñón I. A quantum mechanics/molecular mechanics study of the protein-ligand interaction of two potent inhibitors of human O-GlcNAcase: PUGNAc and NAG-thiazoline. J Phys Chem B. 2008 Nov 13;112(45):14260-6. doi: 10.1021/jp804626j. Epub 2008 Oct 22. Erratum in: J Phys Chem B. 2010 Feb 11;114(5):2090. PMID: 18939790.

18: Langley DB, Harty DW, Jacques NA, Hunter N, Guss JM, Collyer CA. Structure of N-acetyl-beta-D-glucosaminidase (GcnA) from the endocarditis pathogen Streptococcus gordonii and its complex with the mechanism-based inhibitor NAG- thiazoline. J Mol Biol. 2008 Mar 14;377(1):104-16. doi: 10.1016/j.jmb.2007.09.028. Epub 2007 Sep 16. PMID: 18237743.

19: Kim EJ, Amorelli B, Abdo M, Thomas CJ, Love DC, Knapp S, Hanover JA. Distinctive inhibition of O-GlcNAcase isoforms by an alpha-GlcNAc thiolsulfonate. J Am Chem Soc. 2007 Dec 5;129(48):14854-5. doi: 10.1021/ja076038u. Epub 2007 Nov 10. PMID: 17994748.

20: Plíhal O, Sklenár J, Hofbauerová K, Novák P, Man P, Pompach P, Kavan D, Ryslavá H, Weignerová L, Charvátová-Pisvejcová A, Kren V, Bezouska K. Large propeptides of fungal beta-N-acetylhexosaminidases are novel enzyme regulators that must be intracellularly processed to control activity, dimerization, and secretion into the extracellular environment. Biochemistry. 2007 Mar 13;46(10):2719-34. doi: 10.1021/bi061828m. Epub 2007 Feb 16. PMID: 17302431.