Synonym
Nagstatin; Nagstatine
IUPAC/Chemical Name
Imidazo(1,2-a)pyridine-3-acetic acid, 8-(acetylamino)-5,6,7,8-tetrahydro-6,7-dihydroxy-5-(hydroxymethyl)-
InChi Key
OBMORLCFLUTVPI-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H17N3O6/c1-5(17)14-9-11(21)10(20)7(4-16)15-6(2-8(18)19)3-13-12(9)15/h3,7,9-11,16,20-21H,2,4H2,1H3,(H,14,17)(H,18,19)
SMILES Code
O=C(O)CC1=CN=C2C(NC(C)=O)C(O)C(O)C(CO)N21
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
299.28
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: Shanmugasundaram B, Debowski AW, Dennis RJ, Davies GJ, Vocadlo DJ, Vasella A. Inhibition of O-GlcNAcase by a gluco-configured nagstatin and a PUGNAc-imidazole hybrid inhibitor. Chem Commun (Camb). 2006 Nov 13;(42):4372-4. Epub 2006 Sep 29. PubMed PMID: 17057847.
2: Tatsuta K, Miura S, Ohta S, Gunji H. Syntheses and glycosidase inhibiting activities of nagstatin analogs. J Antibiot (Tokyo). 1995 Mar;48(3):286-8. PubMed PMID: 7730168.
3: Aoyagi T, Suda H, Uotani K, Kojima F, Aoyama T, Horiguchi K, Hamada M, Takeuchi T. Nagstatin, a new inhibitor of N-acetyl-beta-D-glucosaminidase, produced by Streptomyces amakusaensis MG846-fF3. Taxonomy, production, isolation, physico-chemical properties and biological activities. J Antibiot (Tokyo). 1992 Sep;45(9):1404-8. PubMed PMID: 1429224.
4: Aoyama T, Naganawa H, Suda H, Uotani K, Aoyagi T, Takeuchi T. The structure of nagstatin, a new inhibitor of N-acetyl-beta-D-glucosaminidase. J Antibiot (Tokyo). 1992 Sep;45(9):1557-8. PubMed PMID: 1429245.
5: Tatsuta K, Ikeda Y, Miura S. Synthesis and glycosidase inhibitory activities of nagstatin triazole analogs. J Antibiot (Tokyo). 1996 Aug;49(8):836-8. PubMed PMID: 8823523.
6: 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. Review. PubMed PMID: 19664691.
7: Usuki H, Toyo-oka M, Kanzaki H, Okuda T, Nitoda T. Pochonicine, a polyhydroxylated pyrrolizidine alkaloid from fungus Pochonia suchlasporia var. suchlasporia TAMA 87 as a potent beta-N-acetylglucosaminidase inhibitor. Bioorg Med Chem. 2009 Oct 15;17(20):7248-53. doi: 10.1016/j.bmc.2009.08.052. Epub 2009 Aug 31. PubMed PMID: 19775896.
8: Usuki H, Nitoda T, Ichikawa M, Yamaji N, Iwashita T, Komura H, Kanzaki H. TMG-chitotriomycin, an enzyme inhibitor specific for insect and fungal beta-N-acetylglucosaminidases, produced by actinomycete Streptomyces anulatus NBRC 13369. J Am Chem Soc. 2008 Mar 26;130(12):4146-52. doi: 10.1021/ja077641f. Epub 2008 Feb 29. PubMed PMID: 18307344.
