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Benesudon

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Category Antibiotics
Catalog number BBF-00280
CAS 189506-36-3
Molecular Weight 296.36
Molecular Formula C16H24O5

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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

Benesudon is produced by the strain of Mollisia benesuada. MIC 2.5-10μg/mL was found to be resistant to gram-positive bacteria, negative bacteria, yeast and fungi. It's cytotoxic and its IC50 of L1 210, RBL, BHK21 and B1 6-F1 cells is 1-2μg/mL.

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IUPAC Name (4R,5R,6R)-6-heptyl-4,5-dihydroxy-5-methyl-2-methylidene-4,6-dihydrofuro[2,3-b]pyran-3-one
Canonical SMILES CCCCCCCC1C(C(C2=C(O1)OC(=C)C2=O)O)(C)O
InChI InChI=1S/C16H24O5/c1-4-5-6-7-8-9-11-16(3,19)14(18)12-13(17)10(2)20-15(12)21-11/h11,14,18-19H,2,4-9H2,1,3H3/t11-,14-,16+/m1/s1
InChI Key IOBWHXDKGUYSRG-XFJVYGCCSA-N
Appearance Colorless Oil
Antibiotic Activity Spectrum gram-positive bacteria; gram-negative bacteria; fungi; yeast
1. Synthesis of the core structure of the fungal metabolite benesudon: use of oxidative decarboxylation
Derrick L J Clive, Minaruzzaman, Haikang Yang Org Lett. 2005 Dec 8;7(25):5581-3. doi: 10.1021/ol052131g.
[chemical reaction: see text]. The core structure (5) of the fungal metabolite benesudon (1) was synthesized, the key step being oxidative decarboxylation of acid 17.
2. Oxidative decarboxylation as a route to ketene acetals: assignment of relative and absolute stereochemistry to the fungal metabolite benesudon by total synthesis
Derrick L J Clive, Minaruzzaman Org Lett. 2007 Dec 6;9(25):5315-7. doi: 10.1021/ol702509a. Epub 2007 Nov 8.
The unusual ketene acetal benesudon, which is a bioactive fungal metabolite, was synthesized from d-glucose by a route involving radical cyclization to form the five-membered ring and oxidative decarboxylation to generate the key central double bond. The originally suggested stereochemistry for the quaternary center C(5) must be revised, as both possibilities were prepared and a comparison with an authentic sample was made. The absolute configuration of benesudon is 4S,5R,6S.
3. The naturally occurring ketene acetal benesudon: total synthesis and assignment of relative and absolute stereochemistry
Derrick L J Clive, Minaruzzaman, Haikang Yang J Org Chem. 2008 Sep 5;73(17):6743-52. doi: 10.1021/jo801028y. Epub 2008 Aug 2.
The densely functionalized ketene acetal benesudon, which is a bioactive fungal metabolite, was synthesized from D-glucose by a route involving radical cyclization to form the five-membered ring, and oxidative decarboxylation to generate the key central double bond. The originally suggested stereochemistry for the quaternary center C(5) must be revised, as both C(5) epimers were prepared and a comparison with an authentic sample was made. The absolute configuration of benesudon is 4S,5R,6S.

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