Nectrisine

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MedKoo CAT#: 584836

CAS#: 108692-47-3

Description: Nectrisine is an inhibitor of alpha-glucosidases produced by the fungus, Nectria lucida F-4490.


Price and Availability

Size Price Shipping out time Quantity
Inquire bulk and customized quantity

Pricing updated 2020-09-28. Prices are subject to change without notice.

Nectrisine 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#: 584836
Name: Nectrisine
CAS#: 108692-47-3
Chemical Formula: C5H9NO3
Exact Mass: 131.0582
Molecular Weight: 131.131
Elemental Analysis: C, 45.80; H, 6.92; N, 10.68; O, 36.60


Synonym: Nectrisine; FR 900483; WF 4490

IUPAC/Chemical Name: (2R-(2-alpha,3-beta,4-alpha))-3,4-Dihydro-2-(hydroxymethyl)-2H-pyrrole-3,4-diol

InChi Key: QUPCOXZVKXONSC-UOWFLXDJSA-N

InChi Code: InChI=1S/C5H9NO3/c7-2-3-5(9)4(8)1-6-3/h1,3-5,7-9H,2H2/t3-,4-,5-/m1/s1

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


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).

HS Tariff Code:
2934.99.9001


References

1: Miyauchi R, Sakurai H, Shiba Y. Characterization of a novel oxidase from Thelonectria discophora SANK 18292 involved in nectrisine biosynthesis. AMB Express. 2016 Mar;6(1):6. doi: 10.1186/s13568-016-0176-1. Epub 2016 Jan 20. PubMed PMID: 26786316; PubMed Central PMCID: PMC4718913.

2: Shibata T, Nakayama O, Tsurumi Y, Okuhara M, Terano H, Kohsaka M. A new immunomodulator, FR-900483. J Antibiot (Tokyo). 1988 Mar;41(3):296-301. PubMed PMID: 3366688.

3: Miyauchi R, Takatsu T, Suzuki T, Ono Y, Shiba Y. Biosynthesis of nectrisine in Thelonectria discophora SANK 18292. Phytochemistry. 2015 Aug;116:87-93. doi: 10.1016/j.phytochem.2015.03.011. Epub 2015 Apr 9. PubMed PMID: 25865736.

4: Miyauchi R, Ono C, Ohnuki T, Shiba Y. Nectrisine Biosynthesis Genes in Thelonectria discophora SANK 18292: Identification and Functional Analysis. Appl Environ Microbiol. 2016 Oct 14;82(21):6414-6422. Print 2016 Nov 1. PubMed PMID: 27565616; PubMed Central PMCID: PMC5066358.

5: Soriano S, Azzouz M, Llaveria J, Marcé P, Matheu MI, Díaz Y, Castillón S. Enantioselective Formal Synthesis of Nectrisine Using a Palladium-Catalyzed Asymmetric Allylic Amination and Cross-Metathesis as Key Steps. J Org Chem. 2016 Jun 17;81(12):5217-21. doi: 10.1021/acs.joc.6b00494. Epub 2016 Jun 2. PubMed PMID: 27182738.

6: Ribes C, Falomir E, Carda M, Marco JA. Short, stereoselective synthesis of the naturally occurring pyrrolidine radicamine B and a formal synthesis of nectrisine. J Org Chem. 2008 Oct 3;73(19):7779-82. doi: 10.1021/jo8012989. Epub 2008 Sep 3. PubMed PMID: 18763826.

7: Tsujii E, Muroi M, Shiragami N, Takatsuki A. Nectrisine is a potent inhibitor of alpha-glucosidases, demonstrating activities similarly at enzyme and cellular levels. Biochem Biophys Res Commun. 1996 Mar 18;220(2):459-66. PubMed PMID: 8645327.

8: Kayakiri H, Nakamura K, Takase S, Setoi H, Uchida I, Terano H, Hashimoto M, Tada T, Koda S. Structure and synthesis of nectrisine, a new immunomodulator isolated from a fungus. Chem Pharm Bull (Tokyo). 1991 Nov;39(11):2807-12. PubMed PMID: 1799935.

9: Tschamber T, Gessier F, Dubost E, Newsome J, Tarnus C, Kohler J, Neuburger M, Streith J. Carbohydrate transition state mimics: synthesis of imidazolo-pyrrolidinoses as potential nectrisine surrogates. Bioorg Med Chem. 2003 Aug 15;11(17):3559-68. PubMed PMID: 12901900.