Synonym
PUGNAc; (Z)-PugNAc; Nac-lapco; Nac lapco
IUPAC/Chemical Name
N-((3R,4R,5S,6R,Z)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((phenylcarbamoyl)oxy)imino)tetrahydro-2H-pyran-3-yl)acetamide
InChi Key
PBLNJFVQMUMOJY-JXZOILRNSA-N
InChi Code
InChI=1S/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
SMILES Code
CC(=O)N[C@@H]\1[C@H]([C@@H]([C@H](O/C1=N\OC(=O)NC2=CC=CC=C2)CO)O)O
Appearance
To be determined
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
353.33
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.
| 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 |
1: Okuda T. PUGNAc treatment provokes globotetraosylceramide accumulation
in human umbilical vein endothelial cells. Biochem Biophys Res Commun. 2017 May
20;487(1):76-82. doi: 10.1016/j.bbrc.2017.04.019. Epub 2017 Apr 6. PMID:
28392398.
2: Park JH, Lee JE, Moon PG, Baek MC. PUGNAc induces protein ubiquitination in
C2C12 myotube cells. Cell Biochem Funct. 2015 Dec;33(8):525-33. doi:
10.1002/cbf.3150. Epub 2015 Nov 4. PMID: 26531776.
3: Teo CF, El-Karim EG, Wells L. Dissecting PUGNAc-mediated inhibition of the
pro-survival action of insulin. Glycobiology. 2016 Nov;26(11):1198-1208. doi:
10.1093/glycob/cww043. Epub 2016 Apr 12. PMID: 27072814; PMCID: PMC5884396.
4: Mehdy A, Morelle W, Rosnoblet C, Legrand D, Lefebvre T, Duvet S, Foulquier F.
PUGNAc treatment leads to an unusual accumulation of free oligosaccharides in
CHO cells. J Biochem. 2012 Apr;151(4):439-46. doi: 10.1093/jb/mvs012. Epub 2012
Feb 15. PMID: 22337894.
5: Whitworth GE, Macauley MS, Stubbs KA, Dennis RJ, Taylor EJ, Davies GJ, Greig
IR, Vocadlo DJ. 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. 2007 Jan
24;129(3):635-44. doi: 10.1021/ja065697o. PMID: 17227027.
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