Abikoviromycin

Abikoviromycin

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Abikoviromycin
Category Antibiotics
Catalog number BBF-00001
CAS 31774-33-1
Molecular Weight 161.20
Molecular Formula C10H11NO
Purity ≥90%

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Description

Abikoviromycin is an antiviral antibiotic piperidine alkaloid produced by the bacteria Streptomyces abikoensis and Streptomyces rubescens. The dilution of Abikoviromycin has the effect of anti-Eastern and Western equine encephalitis virus, but has no effect on Venezuelan virus.

Specification

Synonyms Latumcidin; Abicoviromycin; Cyclopent(b)oxireno(c)pyridine, 7-ethylidene-1a,2,3,7-tetrahydro-, (1aR,7E,7aS)-; Cyclopent(b)oxireno(c)pyridine, 7-ethylidene-1a,2,3,7-tetrahydro-, (1aR-(1aR*,7E,7aS*))-; Cyclopent(b)oxireno(c)pyridine, 7-ethylidene-1a,2,3,7-tetrahydro-, (E)-(1aS,7aR)-; Virocidin; (1aR,7E,7aS)-7-Ethylidene-1a,2,3,7-tetrahydrocyclopent[b]oxireno[c]pyridine
Storage Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
IUPAC Name (1S,3R,10Z)-10-ethylidene-2-oxa-6-azatricyclo[5.3.0.01,3]deca-6,8-diene
Canonical SMILES CC=C1C=CC2=NCCC3C12O3
InChI InChI=1S/C10H11NO/c1-2-7-3-4-8-10(7)9(12-10)5-6-11-8/h2-4,9H,5-6H2,1H3/b7-2-/t9-,10+/m1/s1
InChI Key KQSFHAWSULOGRI-LPPIIHRRSA-N

Properties

Appearance Solid Powder
Antibiotic Activity Spectrum viruses
Boiling Point 278.8±40.0°C (Predicted)
Melting Point 140-141°C
Density 1.30±0.1 g/cm3 (Predicted)
Solubility Soluble in DMSO

Reference Reading

1. Concise Asymmetric Syntheses of Streptazone A and Abikoviromycin*
Gustav J Wørmer, Nikolaj L Villadsen, Peter Nørby, Thomas B Poulsen Angew Chem Int Ed Engl. 2021 May 3;60(19):10521-10525. doi: 10.1002/anie.202101439. Epub 2021 Mar 18.
Streptazone A and abikoviromycin are alkaloids that both feature an unusual arrangement of reactive functionalities within a compact tricyclic ring system. Here, we report a highly concise asymmetric synthesis of both natural products. The route first constructs another family member, streptazone B1 , using a rhodium-catalyzed distal selective allene-ynamide Pauson-Khand reaction. A regio- and enantioselective epoxidation under chiral phase-transfer catalytic conditions directly afforded streptazone A in 8 steps overall. In one additional step, a chemoselective, iridium-catalyzed reduction of the enaminone system then gave abikoviromycin. The reactivity of streptazone A towards a cysteine mimic, N-acetylcysteamine, was studied and revealed unanticipated transformations, including bis-thiol conjugation which may proceed via formation of a cyclopentadienone intermediate. With flexible access to these compounds, studies aimed to identify their direct biological targets are now possible.

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