Soraphen A

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Structural formula
Structural formula of Soraphen A
General
Surname Soraphen A
Molecular formula C 29 H 44 O 8
External identifiers / databases
CAS number 122547-72-2
EC number 695-712-7
ECHA InfoCard 100.224.388
PubChem 5281897
ChemSpider 4943557
DrugBank DB02859
Wikidata Q21051153
properties
Molar mass 520.65 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Soraphen A is a fungicidally active macrolide from the Soraphene family . It was isolated in 1986 by Hans Reichenbach and Gerhard Höfle as a metabolic product of the myxobacterium Sorangium cellulosum .

Extraction and presentation

The total synthesis of Soraphen A succeeded in 1994 after previous retrosynthetic analysis .

The biosynthesis takes place on the polyketide route .

effectiveness

Soraphen A inhibits the acetyl-CoA carboxylase of fungi, which is necessary for fatty acid synthesis . The connection is extremely effective: Venturia inaequalis (apple scab) is completely inhibited from 10 g · hl −1 ; Botrytis cinerea (gray mold) from 25 g · hl −1 and a seed dressing with 30 g · 100 kg −1 prevents infection with Erysiphe graminis (powdery mildew).

The soraphen yield increased from 3 mg l −1 in 1986 to 1.5 g l −1 in 1990.

The development was discontinued on the basis of toxicological studies with rats, which indicated a teratogenic potential. However, the lead structure promises further potential.

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ a b entry on Soraphene. In: Römpp Online . Georg Thieme Verlag, accessed on August 19, 2015.
  3. ↑ a b Stephan Abel, Dominik Faber, Ottmar Hüter, Bernd Giese: Total synthesis of Soraphen A 1α . In: Angewandte Chemie . tape 106 , no. 23-24 , January 1994, doi : 10.1002 / anie.19941062312 .
  4. ↑ EP 282455.
  5. ↑ Donald B. Jump, Moises Torres-Gonzalez, L. Karl Olson: Soraphen A, an inhibitor of acetyl CoA carboxylase activity, interferes with fatty acid elongation . In: Biochemical Pharmacology . tape 81 , no. January 5 , 2011, doi : 10.1016 / j.bcp.2010.12.014 .
  6. ↑ a b Nature as an example. Natural product research in Germany , pp. 67–68 (50 MB).
  7. ↑ Hans Reichenbach, microbiologist: Der Marathon-Mann , in: Brand eins 04/2014, p. 156 ff.