Nojirimycin

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

MedKoo CAT#: 585299

CAS#: 15218-38-9

Description: Nojirimycin is the parent compound of a class of antibiotics and glycosidase inhibitors obtained from a class of Streptomyces species.

Chemical Structure

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Nojirimycin
CAS# 15218-38-9
Instruction

Theoretical Analysis

MedKoo Cat#: 585299
Name: Nojirimycin
CAS#: 15218-38-9
Chemical Formula: C6H13NO5
Exact Mass: 179.08
Molecular Weight: 179.172
Elemental Analysis: C, 40.22; H, 7.31; N, 7.82; O, 44.65

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Nojirimycin; R 468; R468; R-468; U 51640; U51640; U-51640

IUPAC/Chemical Name: (3R,4S,5R,6R)-6-(hydroxymethyl)piperidine-2,3,4,5-tetrol

InChi Key: BGMYHTUCJVZIRP-GASJEMHNSA-N

InChi Code: InChI=1S/C6H13NO5/c8-1-2-3(9)4(10)5(11)6(12)7-2/h2-12H,1H2/t2-,3-,4+,5-,6?/m1/s1

SMILES Code: OC1N[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

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).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 179.17 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:
In vitro protocol:
In vivo protocol:

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Reconstitution Calculator

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1: Tsuruoka T, Fukuyasu H, Ishii M, Usui T, Shibahara S, Inouye S. Inhibition of mouse tumor metastasis with nojirimycin-related compounds. J Antibiot (Tokyo). 1996 Feb;49(2):155-61. PubMed PMID: 8621356.

2: Xu Y, Choi SR, Kung MP, Kung HF. Synthesis of radioiodinated 1-deoxy-nojirimycin derivatives: novel glucose analogs. Nucl Med Biol. 1999 Oct;26(7):833-9. PubMed PMID: 10628565.

3: Brumshtein B, Aguilar-Moncayo M, Benito JM, García Fernandez JM, Silman I, Shaaltiel Y, Aviezer D, Sussman JL, Futerman AH, Ortiz Mellet C. Cyclodextrin-mediated crystallization of acid β-glucosidase in complex with amphiphilic bicyclic nojirimycin analogues. Org Biomol Chem. 2011 Jun 7;9(11):4160-7. doi: 10.1039/c1ob05200d. Epub 2011 Apr 11. PubMed PMID: 21483943.

4: Mitchell EP, Withers SG, Ermert P, Vasella AT, Garman EF, Oikonomakos NG, Johnson LN. Ternary complex crystal structures of glycogen phosphorylase with the transition state analogue nojirimycin tetrazole and phosphate in the T and R states. Biochemistry. 1996 Jun 11;35(23):7341-55. PubMed PMID: 8652510.

5: Viuff AH, Besenbacher LM, Kamori A, Jensen MT, Kilian M, Kato A, Jensen HH. Stable analogues of nojirimycin--synthesis and biological evaluation of nojiristegine and manno-nojiristegine. Org Biomol Chem. 2015 Oct 7;13(37):9637-58. doi: 10.1039/c5ob01281c. PubMed PMID: 26264193.

6: Bini D, Cardona F, Forcella M, Parmeggiani C, Parenti P, Nicotra F, Cipolla L. Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors. Beilstein J Org Chem. 2012;8:514-21. doi: 10.3762/bjoc.8.58. Epub 2012 Apr 5. PubMed PMID: 22509223; PubMed Central PMCID: PMC3326631.

7: Tyrrell BE, Sayce AC, Warfield KL, Miller JL, Zitzmann N. Iminosugars: Promising therapeutics for influenza infection. Crit Rev Microbiol. 2017 Sep;43(5):521-545. doi: 10.1080/1040841X.2016.1242868. Epub 2016 Dec 8. Review. PubMed PMID: 27931136; PubMed Central PMCID: PMC5470110.

8: Argoudelis AD, Reusser F, Mizsak SA, Baczynskyj L. Antibiotics produced by Streptomyces ficellus II. Feldamycin and nojirimycin. J Antibiot (Tokyo). 1976 Oct;29(10):1007-14. PubMed PMID: 994320.

9: Godin G, Compain P, Masson G, Martin OR. A general strategy for the practical synthesis of nojirimycin C-glycosides and analogues. Extension to the first reported example of an iminosugar 1-phosphonate. J Org Chem. 2002 Oct 4;67(20):6960-70. PubMed PMID: 12353989.

10: Niwa T, Tsuruoka T, Goi H, Kodama Y, Itoh J, Inouye S, Yamada Y, Niida T, Nobe M, Ogawa Y. Novel glycosidase inhibitors, nojirimycin B and D-mannonic-delta-lactam. Isolation, structure determination and biological property. J Antibiot (Tokyo). 1984 Dec;37(12):1579-86. PubMed PMID: 6549315.

11: Cipolla L, Fernandes MR, Gregori M, Airoldi C, Nicotra F. Synthesis and biological evaluation of a small library of nojirimycin-derived bicyclic iminosugars. Carbohydr Res. 2007 Sep 3;342(12-13):1813-30. Epub 2007 Apr 18. PubMed PMID: 17477911.

12: Fuhrmann U, Bause E, Ploegh H. Inhibitors of oligosaccharide processing. Biochim Biophys Acta. 1985 Jun 24;825(2):95-110. Review. PubMed PMID: 3159432.

13: Nauerth A, Lemansky P, Hasilik A, von Figura K, Bause E, Legler G. Cell type dependent inhibition of transport of cathepsin D in HepG2 cells and fibroblasts exposed to deoxy-manno-nojirimycin and deoxynojirimycin. Biol Chem Hoppe Seyler. 1985 Nov;366(11):1009-16. PubMed PMID: 2934077.

14: Brumshtein B, Aguilar-Moncayo M, García-Moreno MI, Ortiz Mellet C, García Fernández JM, Silman I, Shaaltiel Y, Aviezer D, Sussman JL, Futerman AH. 6-Amino-6-deoxy-5,6-di-N-(N'-octyliminomethylidene)nojirimycin: synthesis, biological evaluation, and crystal structure in complex with acid beta-glucosidase. Chembiochem. 2009 Jun 15;10(9):1480-5. doi: 10.1002/cbic.200900142. PubMed PMID: 19437524.

15: Stavale EJ, Vu H, Sampath A, Ramstedt U, Warfield KL. In vivo therapeutic protection against influenza A (H1N1) oseltamivir-sensitive and resistant viruses by the iminosugar UV-4. PLoS One. 2015 Mar 18;10(3):e0121662. doi: 10.1371/journal.pone.0121662. eCollection 2015. PubMed PMID: 25786028; PubMed Central PMCID: PMC4364785.

16: Tsukamoto K, Uno A, Kubota Y, Shimada S, Hori Y, Imokawa G. Role of asparagine-linked carbohydrates in pulmonary metastasis of B16-F10 murine melanoma cells: implication through glycosylation inhibition by nojirimycin. Melanoma Res. 1992 May;2(1):33-9. PubMed PMID: 1643422.

17: Dubernet M, Defoin A, Tarnus C. Asymmetric synthesis of the L-fuco-nojirimycin, a nanomolar alpha-L-fucosidase inhibitor. Bioorg Med Chem Lett. 2006 Mar 1;16(5):1172-4. Epub 2005 Dec 20. PubMed PMID: 16376079.

18: Suzuki H, Ohto U, Higaki K, Mena-Barragán T, Aguilar-Moncayo M, Ortiz Mellet C, Nanba E, Garcia Fernandez JM, Suzuki Y, Shimizu T. Structural basis of pharmacological chaperoning for human β-galactosidase. J Biol Chem. 2014 May 23;289(21):14560-8. doi: 10.1074/jbc.M113.529529. Epub 2014 Apr 15. PubMed PMID: 24737316; PubMed Central PMCID: PMC4031513.

19: Hettkamp H, Bause E, Legler G. Inhibition by nojirimycin and 1-deoxynojirimycin of microsomal glucosidases from calf liver acting on the glycoprotein oligosaccharides Glc1-3Man9GlcNAc2. Biosci Rep. 1982 Nov;2(11):899-906. PubMed PMID: 6218840.

20: Atsumi S, Iinuma H, Nosaka C, Umezawa K. Biological activities of cyclophellitol. J Antibiot (Tokyo). 1990 Dec;43(12):1579-85. PubMed PMID: 2148935.