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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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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product 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.

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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
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
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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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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