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(E)-Pterulinic acid

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Category Enzyme inhibitors
Catalog number BBF-03284
CAS 190143-30-7
Molecular Weight 290.70
Molecular Formula C15H11ClO4

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Fermentation Lab

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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

(E)-Pterulinic acid is a Coenzyme I: Coenzyme Q oxidoreductase inhibitor produced by Pterula sp. 82168. It has anti-yeast and filamentous fungus effect and has cytotoxic activity.

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Synonyms ME-82168-N; Pterulinic acid
IUPAC Name 2-[(7E)-7-(chloromethylidene)furo[3,2-h][1]benzoxepin-2-yl]acetic acid
Canonical SMILES C1C(=CCl)C=CC2=C(O1)C=C3C(=C2)C=C(O3)CC(=O)O
InChI InChI=1S/C15H11ClO4/c16-7-9-1-2-10-3-11-4-12(5-15(17)18)20-14(11)6-13(10)19-8-9/h1-4,6-7H,5,8H2,(H,17,18)/b9-7+
InChI Key MMKVRUNBWGNULK-VQHVLOKHSA-N
Appearance Yellow Crystal
Antibiotic Activity Spectrum fungi; yeast
Boiling Point 501.0±50.0°C at 760 mmHg
Melting Point 152-154°C
Density 1.492±0.06 g/cm3
1. Pterulinic acid and pterulone, two novel inhibitors of NADH:ubiquinone oxidoreductase (complex I) produced by a Pterula species. II. Physico-chemical properties and structure elucidation
M Engler, T Anke, O Sterner J Antibiot (Tokyo). 1997 Apr;50(4):330-3. doi: 10.7164/antibiotics.50.330.
The structures of two novel fungal antibiotics, isolated from a Pterula species, that interfere with the NADH:ubiquinone oxidoreductase and inhibit the respiration of eucaryotes, were determined by spectroscopic techniques. Both compounds, pterulinic acid (1a) and pterulone (2), contain a 1-benzoxepin ring system and are chlorinated. Pterulinic acid (1a), which was obtained as a 1:5 inseparable mixture of the two isomers (Z)-1a and (E)-1a, in addition contains a furan. Their structures were determined by mass spectrometry and NMR spectroscopy, and 2D heteronuclear correlation experiments permitted the assignment of all NMR signals.

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