Nectrisine | CAS#108692-47-3 | inhibitor

MedKoo Cat#: 584836 | Name: Nectrisine

Description:

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

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

Chemical Structure

Nectrisine

CAS#108692-47-3

Theoretical Analysis

MedKoo Cat#: 584836

Name: Nectrisine

CAS#: 108692-47-3

Chemical Formula: C5H9NO3

Exact Mass: 131.0582

Molecular Weight: 131.13

Elemental Analysis: C, 45.80; H, 6.92; N, 10.68; O, 36.60

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

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

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 131.13 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: 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.