Nagstatin

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 584888

CAS#: 126844-81-3

Description: Nagstatin is an inhibitor of N-acetyl-beta-D-glucosaminidase and is produced by Streptomyces amakusaensis MG846-fF3.


Price and Availability

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Nagstatin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 584888
Name: Nagstatin
CAS#: 126844-81-3
Chemical Formula: C12H17N3O6
Exact Mass: 299.1117
Molecular Weight: 299.283
Elemental Analysis: C, 48.16; H, 5.73; N, 14.04; O, 32.07


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


Technical Data

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:
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).

Harmonized System Code:
2934990300


References

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.